Preparation of magnetic Schiff base nanocomposites for removal of Rhodamine B

Preparation of magnetic Schiff base nanocomposites for removal of Rhodamine B | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Preparation of magnetic Schiff base nanocomposites for removal of Rhodamine B Liuqing Li, Zhengwen Wei, Xiang-fei Lü, Zhen-Yi Jiang, Wei Wang This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6728589/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 29 Oct, 2025 Read the published version in Chemical Papers → Version 1 posted 5 You are reading this latest preprint version Abstract Magnetic inorganic/organic hybrid materials were prepared by situ polymerization method from o-Tolidine and p-phthalaldehyde. The study employed various techniques to characterize morphology and phase composition. Rhodamine B was select as the indicator pollutants to investigate the adsorption capability of magnetic inorganic/organic hybrid materials, The magnetic schiff base composite materials have excellent adsorption capacity. The density functional theory calculation (DFT) is employed to understand the structural optimization and adsorption energy in different adsorption configuration modes. During the adsorption process, rhodamine B molecules are mainly dominated by the π-π force, accompanied by van der Waals force, hydrophobic interaction, electrostatic attraction and electron donor-acceptor interaction. Schiff base polymer shells provide numerous active sites for rhodamine B adsorption, and Fe 3 O 4 magnetic cores of the inorganic/organic hybrid materials separated the adsorbed rhodamine B from wastewater easily. This kind of magnetic inorganic/organic hybrid materials have potential application in organic dyes removing. Absorption Chemical synthesis Core/shell Magnetic properties Polymer X-ray photoelectron spectroscopy (XPS) Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Figure 10 Introduction In the last decades, with the rapid development of the economy, environmental pollution problems have become great challenges for the sustainable development of society(Cao et al. 2023 ; Kazem et al. 2025 ; Ting-Ting Liu et al. 2024a ). Different organic pollutants, such as organic dyes, antibiotics, cosmetics and food additives, have been detected in environmental samples(Jain et al. 2018 ; Kaur et al. 2022 ). These organic pollutants are not only difficult to degrade naturally, but also lead to the serious environmental disasters(Sudhamayee et al. 2025 ; Xiao-Qian et al. 2025 ). Organic pollutants have the characteristics of poor biodegradability, high toxicity, teratogenicity, thus which not only affects the aesthetics of the environment but also does harm to human body(Okpara et al. 2024 ). Rhodamine B is a kind of triphenylmethane alkaline water-soluble organic dye with fresh peach color, which is used in the textile industry, colored glass, and other industries(Nilmadhab et al. 2025 ). For the treatment of rhodamine B wastewater, several techniques, such as photolysis(Pooja et al. 2025 ), electrocatalytic oxidation(Yitong et al. 2025 ), biological treatments(Kashama et al. 2025 ) and advanced oxidation(Phuong Hoang et al. 2024 ) have been used to eliminate organic pollutants effluents. Photocatalytic degradation of rhodamine B has been extensively investigated for green and environmentally friendly features in the last decades. However, the shortcomings of photocatalytic degradation, such as insufficient adsorption capacity, secondary pollution, speedy recombination of photogenerated electrons and holes and inferior migration capacity still restrict the application of photocatalytic technology (Kavya et al. 2021 ; Yan et al. 2024 ). Advanced oxidation is the organic pollutants treatment technique that utilizes strong oxidizing substances (ozone, hydroxyl radicals, etc.) to react with dissolved pollutants in wastewater to degrade the organic molecular structure(Miaomiao et al. 2025 ). It is inevitable to introduce some chemical reagents in system for strong oxidizing substances production while to use the advanced oxidation technology(Qiufeng et al. 2024 ). Electrocatalytic oxidation refers to the electrode, electrolyte interface charge transfer to accelerate the reaction of catalytic oxidation, which can effectively reduce the activation energy of the interfacial electric field reaction system to promote the reaction so that the organic pollutants in the anode are rapidly degraded(Wenxuan et al. 2025 ). Biological treatment method is a cost-effective and environmentally friendly approach to eliminate organic pollutants, and this technique benefits greatly from the flexibility of numerous microorganisms in degrading various compounds. However, organic pollutants effluents are poor in nutrients, consequently, nutritional supplements (such as nitrogen, carbon and phosphorus sources) are often necessary to improve treatment effect(Bornali et al. 2025 ). In numerous treatment technologies, adsorption, a method of removing organic pollutants by adsorbents, is widely utilized because of its favorable efficiency and easy operation(Ruisi Qiu et al. 2024b ). The adsorbents for rhodamine B include biochar materials(Behera et al. 2024 ), organic-inorganic nanomaterials(Yuan et al. 2024 ), organic skeleton materials (Terrón et al. 2024 )etc. However, the adsorbent is powder form in general, which increases comprehensive treatment processes(Chen Zhang et al. 2020 ). And the rapid recovery treatment of water pollution adsorption materials has become a research hotspot in recent years(Saad et al. 2022 ). Due to easy separation, magnetic nanoparticles have been extensively researched for removal organic pollutants in wastewater. Ouyang et al. used magnetic materials to prepare Porous β-CD polymer (CDP) composite material to adsorb organic pollutants. The adsorbent has higher adsorption capacity and good reusability than previously reported materials(Jinya et al. 2023 ). Qiu et al. developed wood fiber loaded with nano-scale zero-valent iron to improve the magnetic and dye-degrading ability of wood fiber(Dongxu Qiu et al. 2024a ). Joshiba et al. prepared Fe 3 O 4 @SiO 2 with pseudomonas fluorescens biomass in calcium alginate beads (MSAB) as the bioadsorbent to eliminate rhodamine B in water systems(Janet et al. 2021 ). Schiff base is a kind of chemical substance which content the imine group (-C = N-)(Edyta et al. 2022 ), and the imine group provides a distinct function in generating these molecules with wide application in wastewater treatment(Xiaofei Zhang et al. 2012 ). Moreover, Schiff base is easy to synthesize, and the aromaticity of Schiff base polymer will increase when the more aromaticity units is used in the synthesize processes, which will lead to the stronger π-π interactions between organic pollutants and Schiff base polymer(Zhengwen et al. 2021 ). Pawariya et al. synthesized the chitosan-based Schiff base materials modified with citric acid with high efficiency capacity for dyes from wastewater(Pawariya et al. 2024 ). Although magnetic nanoparticle complicated with Schiff base polymer to form magnetic hybrid materials has been researched somewhat, but not extensively over the adsorption removing mechanism on the density functional theory (DFT) calculation view. In this paper, magnetic Schiff base hybrid materials were prepared by situ polymerization method from o-Tolidine and p-phthalaldehyde. And Schiff base polymer molecular content plenty of benzene rings and naphthalene rings, increasing the π-π stacking interaction between rhodamine B and Schiff base polymer, and Fe 3 O 4 magnetic cores of the inorganic/organic hybrid materials separated the adsorbed rhodamine B from wastewater easily. Density functional theory (DFT) was used to explore the adsorption energy, adsorption mode and adsorption mechanism. Materials and methods Materials O-Tolidine (C 14 H 16 N 2 ), p-phthalaldehyde (C 8 H 6 O 2 ) and nano-ferric tetroxide (Fe 3 O 4 ) were obtained from Aladdin Chemical Reagent Limited Company (Shanghai, China). Sodium dodecyl sulfate (CH 3 (CH 2 ) 11 OSO 3 Na) was bought from Damao Chemical Reagent Limited Company (Tianjin China). Rhodamine B (C 28 H 31 ClN 2 O 3 ) was bought from Fuchen Chemical Reagent Limited Company (Tianjin China). Nitric Acid (HNO 3 , 65–68 wt%), sodium hydroxide (NaOH) and ethanol (C₂H₅OH) were supplied by Xian Chemical Reagent Factory (Xi’an China). Magnetic composite materials preparation The polycondensation reaction pathway diagram from o-tolidine and p-phthalaldehyde is shown in Fig. S1 . The flow chart of magnetic composite materials preparation is shown in Fig. S2. The specific preparation processes are described as follows. Magnetic schiff base inorganic/organic hybrid materials were synthesized by one-pot embedding method. Firstly, 0.335 g of p-phthalaldehyde was dissolved in 40 mL anhydrous ethanol named solution A, and 0.53 g of o-tolidine was dissolved in 40 mL anhydrous ethanol named solution B. Secondly, Solution A was mixed with solution B at 25°C for 24 hours continuously stirring. Then, yellow sediments were formed in this stage. Finally, Schiff base polymers (OTTP) were obtained after filtration, washing and drying. Magnetic inorganic/organic hybrid materials were prepared through two synthetic pathways. Nano-ferric tetroxide was weighed 0.65g accurately and suspended in 40 mL deionized water to form the suspension A. Subsequently, 0.2 g of OTTP and 0.25 g of sodium dodecyl sulfate were suspended in 100 mL deionized water, the suspension B was formed after adjusting (2M HNO 3 ) the pH to 2. Then, suspension A was mixed with suspension B at room temperature and stirred 3 hours. Finally, the magnetic hybrid materials (named Fe 3 O 4 -OTTP-1) was prepared after magnetic separation, washing and drying. Another synthetic pathway of magnetic inorganic/organic hybrid materials is the situ condensation reaction. Firstly, 0.15 g of p-phthalaldehyde was dissolved in 50 mL anhydrous ethanol named solution A, and 0.05 g of o-tolidine was dissolved in 50 mL anhydrous ethanol named solution B. Subsequently, nano-ferric tetroxide was weighed 0.325 g accurately and suspended in 50 mL anhydrous ethanol to form the suspension C. Then, solution A and solution B were added into suspension C with continuously stirred 3 hours at room temperature. Finally, the magnetic hybrid materials (named Fe 3 O 4 -OTTP-2) was prepared after magnetic separation, washing and drying. Characterization Samples were analyzed by Fourier transform infrared (FT-IR) using Nicolet 5700 analyzer. X-ray photoelectron spectroscopy (XPS) instrument (ESCALB Xi + ) was used to determine the elements on the surface of Fe 3 O 4 , OTTP, Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2. X-ray diffraction analyzer (XRD, D8 ADVANCE) was used to research phase and composition of magnetic hybrid materials. The microscopic morphology and element composition of the sample was measured by scanning electron microscope (SEM, S-4800, Hitachi, Japan), equipped with an energy dispersive spectrometer (EDS, INCA-350, Oxford, UK). Transmission electron microscope (TEM, JEM-2100F) was applied to detect the microstructures. The hysteresis loop of samples was performed by the vibrating sample magnetometer (VSM, LAKE 7404). The pore size distribution of the samples was carried out by Brunauer, Emmett and Teller (BET, NOVA 2000, USA). Nuclear Magnetic Resonance (NMR, AVANCE NEO 400MHZ) was used to determine the hydrogen spectrum of samples. The gel permeation chromatography (GPC) experiment was carried out on an Agilent PL-GPC50 analyzer to estimate the average molecular weight. Batch adsorption experiments The absorption behavior of samples for rhodamine B was assessed in batch experiments under different conditions. In the kinetic adsorption experiment, rhodamine B solution was obtained by dissolving 30 mg rhodamine B in 1 L deionized water, Fe 3 O 4 -OTTP-1 (or Fe 3 O 4 -OTTP-2) were weighed 0.14g accurately and placed into 210 mL rhodamine B solution (30 mg/L) respectively, and shaking adsorption reaction for 6 h. The mixed solutions were magnetically separated with different adsorption time. In particular, the supernatant is filtered through a microporous membrane to reduce experimental error. The concentration of rhodamine B were detected by the L6S ultraviolet-visible spectrophotometer, and the adsorption capacity of materials were calculated. The adsorption experiments were repeated three times for decreasing errors, and every data were the arithmetic mean. In the isotherm experiment, 0.02g Fe 3 O 4 -OTTP-1 (or Fe 3 O 4 -OTTP-2) was put into different concentration rhodamine B solution (30 mL) to research thermodynamic process of adsorption. Moreover, the removal performance in relation to different temperature, pH, and adsorbent dosage were investigated as well. Finally, adsorbed Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 were separated from the mixed solution and washed by anhydrous ethanol three times. It was pyrolyzed at 200°C for 3 h and used in the subsequent adsorption reaction for cyclic performance investigation. Theory calculation Theoretical calculation was conducted using GAUSSIAN 16 software. The molecular structure of rhodamine B, Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 were optimized by B3 LYP-D3 method(Zirong Zhang and Collum 2018 ), and the base group 6-311G(d,p) was selected for fast optimization(Tian et al. 2018 ; Zhu et al. 2020 ). The bonding mode of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 with rhodamine B were also optimized by this method. In addition, the M062X-D3 method was utilized to calculate molecular monomer energy, and the M062X-D3-group superposition correction factor was used to calculate the bonding energy, and the group was selected 6-311G+(d,p)(Junhong Wu et al. 2017a ). It is important to note that for the purpose of improving the computational speed and precision of the results, we choose the partial aromatic carbon of rhodamine B for theoretical calculation. In order to analyze the properties of bonding modes, the distribution of molecular orbitals and electrostatic potentials are also obtained(Wei et al. 2022a ). Results and Discussion Fe 3 O 4 , Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 Characterization Surface morphologies of Fe 3 O 4 , OTTP, Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 are shown in Fig. 1 (A-D). Diameter of Fe 3 O 4 nanoparticles is about 20 nm, and the aggregation of nanoparticles take place due to the magnetic forces between particles. OTTP has a three-dimensional micron sheet structure, and these microstructure makes the possesses of inorganic-organic encapsulation is more likely to occur. The SEM image of Fe 3 O 4 -OTTP-1 shows that organic molecular chains play the role of a bridge connection, and Fe 3 O 4 nanoparticles composite with polymer blocks using the intermolecular force. The SEM image of Fe 3 O 4 -OTTP-2 shows that Fe 3 O 4 is encapsulated completely by the Schiff base polymer OTTP, and outside polymer molecular chains could provide more aromatic groups which is benefit for rhodamine B adsorption and removing. The element mapping images corresponding to the scanning electron micrographs of OTTP are shown in Fig. 1 (E-H), the elements of C, N, and O can be seen in the whole area, indicating that polymers have uniformity and high purity. The element of C, N, and O are detected in the mapping images of sample Fe 3 O 4 -OTTP-1 in Fig. 1 (I-M), and the Fe element is observed simultaneously, indicating that Fe 3 O 4 nanoparticles are successfully embedded in the Schiff base polymer. Figure 1 (N-R) is the mapping images of sample Fe 3 O 4 -OTTP-2, and these mapping images are similar with sample Fe 3 O 4 -OTTP-1, signals of C, N, O and Fe are also measured in the final inorganic/organic hybrid materials. Furthermore, by comparing the EDS schematic diagrams of OTTP (Fig. 1 S), Fe 3 O 4 -OTTP-1(Fig. 1 T), and Fe 3 O 4 -OTTP-2(Fig. 1 U), it can be seen that the content of element O in inorganic/organic hybrid materials (Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2). The surface chemical composition and valence state of samples (OTTP, Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2) were analyzed by XPS technology. The XPS spectra of OTTP (Fig. 2 A) show that the peak corresponding to the C element appears at 284 eV, the peak is scribed to the N element appears at 398 eV, and the peak is attributed to the O element appears at 531.5 eV. Meanwhile, with regard to the XPS spectra of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2, it is noticed that not only are the C, N and O elements present, but also the characteristic peak corresponding to the Fe element is detected at 711 eV. Moreover, the high-resolution spectra of elements are used to obtain more comprehensive information, the C1s spectra of OTTP, Fe 3 O 4 -OTTP-1, and Fe 3 O 4 -OTTP-2 are shown in Fig. 2 B, Fig. 2 E and Fig. 2 H respectively. The peak (284.4 eV) is originated from C = C/C-C (Khan et al. 2020 ) and the peak (286.5 eV) is ascribed to C = N (Wei et al. 2022b ) respectively. The N1s spectra of OTTP, Fe 3 O 4 -OTTP-1, and Fe 3 O 4 -OTTP-2 are shown in Fig. 2 C, Fig. 2 F, and Fig. 2 G. Two peaks are found at 379.71 and 401.09 eV respectively, corresponding to N-C and N = C bonds(Shi et al. 2020 ). Figure 2 D, Fig. 2 G, and Fig. 2 K are the O1s spectra of OTTP, Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2, and which are attributed to O = C(Khan et al. 2020 ) bond and O-H bond at 379.71 and 531.17 eV respectively. The characteristic peak appearing at 529.8 eV is ascribed to the O-Fe bond (Khan et al. 2020 ) in Fig. 2 K. The Fe 2p spectrum (Fig. 2 H) has three peaks at 708.21, 709.10, and 725.51 eV, correlating to Fe 2+ 2p 3/2 , Fe 3+ 2p 3/2 , and Fe 3+ 2p 1/2 respectively. In addition, the three satellite peaks at 711.99 eV, 717.7 eV, and 731.32 eV confirm that the iron oxide is Fe 3 O 4 . The distinctive azomethine (N = C) group indicates the effectiveness of the polycondensation reaction of Schiff base polymer synthesis, on the other hand, the aromatic carbon associated with the C = C/C-C group can provide the possibility of adsorbing rhodamine B through the π-π interaction. The distribution of the molecular weight of the OTTP polymer is shown in Fig. 3 A. It can be seen that the molecular weight of OTTP present relatively narrow peak in the curve, indicating that homogeneous molecular chains have formed in the condensation reaction. It is found in the GPC curve that the molecular weight of OTTP distribute within the scope from 700 to 4000, which indicates that the prepared OTTP is an oligomer. The weight-average molecular weight (Mw), number-average molecular weight (Mn), peak molecular weight (Mp), and z-average molecular weight (Mz) of OTTP are 919, 580, 812, and 1468 respectively. It is worth noting that the molecular weight distribution index (PDI = Mw/Mn) is 1.58. When the PDI is close to 1, it represents that the molecular weight shows a relatively narrow distribution characteristic, which means that the uniformity of the polymer molecule size is relatively high. In addition, the Mn value represents the number-weighted average of molecules with different molecular weights in the polymer, reflecting the overall size condition about the polymer molecules. The degree of polymerization is estimated by Mn/the molecular weight of the repeating unit. Polymerization degree of OTTP is 6.99, indicating that the prepared Schiff base polymer (OTTP) belongs to low molecular weight polymer. Figure 3 B is plotted with retention time as the abscissa and response as the ordinate. A narrow and sharp peak is observed in Fig. 3 B (in the 9.25–9.75 retention min region), which indicates that OTTP is oligomer. This outcome agrees with the data of the GPC molecular weight distribution curve, and the molecular weight is centered within the range of 700 to 2000 (particularly in the 1000–2000). The magnetic saturation value of samples is evaluated by VSM. The hysteresis loops of Fe 3 O 4 , Fe 3 O 4 -OTTP-1, and Fe 3 O 4 -OTTP-2 are measured in the magnetic field range of ± 20K Oe, as illustrated in Fig. 3 C. The saturation magnetization of pure magnetic oxide particles is 65.3571 emu/g, and the saturation magnetization of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 is also around 65.3571 emu/g. This phenomenon occurs because considering the influence of economic cost and green chemistry, a small amount of Schiff base polymer to wrap Fe 3 O 4 in the synthesis processes. The magnetic inorganic/organic hybrid material has good magnetism, which lays a certain foundation for the subsequent recycling of materials and reduces environmental pollution and waste of resources. Figure 3 D shows the infrared spectra of Fe 3 O 4 , OTTP, Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2. Samples (Fe3O4, Fe3O4-OTTP-1 and Fe3O4-OTTP-2) have the characteristic peak at 1400 cm − 1 and 571 cm − 1 , which corresponds to the Fe-O bond(Fu et al. 2022 ). The peak at 3432.9 cm − 1 corresponds to the -OH group. There is the characteristic peak at 1350.7 cm − 1 , which is attributed to the symmetric deformation vibration of methyl. The characteristic peak corresponding to the C = N group can be seen at 1592.6 cm − 1 (Hamed et al. 2020 ; Mingxiang Liu et al. 2023 ), indicating that the condensation reaction taking place and C = N bond forming in synthesis possesses. The XRD patterns of samples (Fe 3 O 4 , OTTP, Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2) are shown in Fig. 3 E. There exist six diffraction peaks at 2θ = 30.2°, 35.5°, 43.2°, 53.7°, 57.4°, and 62.5°, which are attributed, respectively, to the (220), (311), (400), (422), (511), and (440) planes of the cubic type (b-Fe 3 O 4 ) phase(Koli et al. 2019 ; Mishra et al. 2020 ). Schiff base organic polymer OTTP has the widen diffraction peak at 10°-15°, which demonstrates that OTTP polymer has better crystallization in comparison with traditional organic chemical compounds. The diffraction peaks of nano-Fe3O4 (30°-65°) and the characteristic diffraction peaks of OTTP (10°-15°) are observed together in samples (Fe3O4-OTTP-1 and Fe3O4-OTTP-2), it reveals that organic phase and inorganic phase co-exist through the synthesis reactions. The N 2 adsorption-desorption isotherms of samples (Fe 3 O 4 , Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2) are shown in Fig. 3 F, and the BET data are listed in S1. The specific surface area of pure nano Fe 3 O 4 is 38.6539 m 2 /g, while those of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 are 34.6209 m 2 /g and 25.8176 m 2 /g respectively. During the modification process of nano Fe 3 O 4 by OTTP, OTTP molecules may block the pores on the particle surface, bringing about the decline of surface area. And the isotherm is type IV, indicating that the inorganic/organic hybrid materials have mesoporous microstructure(Walling et al. 2024 ). According to calculation, the pore diameter of Fe 3 O 4 -OTTP-1 is 17.1571 nm and the pore volume is 0.1519 cm 3 /g, and the pore diameter of Fe 3 O 4 -OTTP-2 is 23.0069 nm and the pore volume is 0.1233 cm 3 /g. The mesoporous structures of inorganic/organic hybrid materials (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2) play important role for removing pollutants in wastewater. The pore size curves of Fe 3 O 4 , Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 are shown in Fig. 3 G, and the relatively wide pores distribution is benefit for pollutants adsorption. The polycondensation reaction synthesis are confirmed by NMR analysis, o-tolidine, terephthalaldehyde and the schiff base polymer OTTP (using tetrahydrofuran-d8 as the solvent) are measured respectively. It can be seen that o-tolidine has an obvious chemical shift at 3.62 ppm, which is ascribe to -NH 3 (Fig. 4 A). As shown in Fig. 4 B, terephthalaldehyde shows obvious signal at 10.07 ppm, in accordance with the aldehyde unit (-CHO). It is worthy noting that the strength of the aldehyde group of OTTP shows weakening tendency. In addition, as shown in Fig. 4 C, OTTP has a new chemical shift at 8.45 ppm, which is originated from the CH = N bond(MuĞLu et al. 2020 ). In addition, some intricate shifts dispersed between 8.32–6.80 ppm may result from hydrogen on the aromatic ring(Hye Kyong Kim et al. 2010 ). These NMR results can be compared together, and the conclusion is obtained clearly that Schiff base condensation reaction is the appropriate approach for polymer preparation. Adsorption performance of magnetic composite materials The adsorption experiments of magnetic inorganic/organic hybrid materials (Fe 3 O 4 -OTTP-1, and Fe 3 O 4 -OTTP-2) were investigated using rhodamine B as the pollutant (Fig. 5 A), and nano Fe 3 O 4 particles was used as the blank reference sample. It can be seen that Fe 3 O 4 -OTTP-1 have the best adsorption capability among all measured samples, and the removal rate of rhodamine B is up to 94.36%. The blank reference sample (nano Fe 3 O 4 particles) possess the lowest adsorption capacity and the lowest removal rate of rhodamine B (Q e = 3.06, removal rate = 6.80%). While nano Fe 3 O 4 particles are encapsulated by Schiff base polymer, the magnetic cores are still maintained and the additional adsorption capability of rhodamine B are endowed by the organic polymers coating. Schiff base polymers coating could interact with rhodamine B through intermolecular forces, such as van der Waals force and π-π stacking, therefore, the adsorption capacity and the removal rate are increase. However, the adsorption capacity of Fe 3 O 4 -OTTP-1 is different from the sample Fe 3 O 4 -OTTP-2, a reasonable explain is that the quantity of organic coating layer is different, the mole ratio (Fe 3 O 4 : OTTP, where OTTP select the molecular weight of basic structural units, 310.4) demonstrates the comparison of relative content of inorganic composition/organic composition, the ratio of Fe 3 O 4 -OTTP-1 is 1.12, which is smaller than the ratio of Fe 3 O 4 -OTTP-2 (5.6), indicating that the more organic molecular basic units are contented in the sample Fe 3 O 4 -OTTP-1 and the more active adsorption sites of rhodamine B are maintained in the sample Fe 3 O 4 -OTTP-1. Adsorption performance of rhodamine B with different conditions In order to evaluate the applicable scope and feasibility of magnetic composites, important factors such as temperature, adsorbent dosage and PH value are taken into consideration. The adsorption capacity and removal rate are researched with different adsorption temperature (20–40°C). It can be observed from Fig. 5 B that the best adsorption performance of all samples is 40°C (Q e1 = 44.26, Remove rate 1 = 98.35%; Q e2 = 18.26, Remove rate 2 = 40.58%). Because the molecule thermal movement velocity increase with the adsorption temperature increasing, the more molecules can reach the surface of the adsorption materials, access to the adsorption sites and undergo adsorption reactions. According to Fig. 5 C, the adsorption capacity of Fe 3 O 4 -OTTP-1 is the largest at 0.005g (Q e1 = 139.08), while the adsorption capacity of Fe 3 O 4 -OTTP-2 is the largest at 0.035g (Q e2 = 10.71). Sample Fe 3 O 4 -OTTP-1 have the higher proportion of adsorption effective active sites at a lower dose (0.005g), which can contact and adsorb rhodamine B, thereby reaching the maximum adsorption capacity. Sample Fe 3 O 4 -OTTP-2 require the higher adsorbent dosage (0.035g) to provide active sites and reach the maximum adsorption capacity. When selected the same adsorbent dosage 0.035g, both materials have enough active sites to absorb rhodamine B, resulting in the maximum removal rate. The effect of PH on rhodamine B adsorption is shown in Fig. 5 D, samples (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2) possess the high removal rates under acidic conditions (Remove rate 1 = 100.00%; Remove rate 2 = 52.58%). In acidic condition, functional groups are easily protonated, making the surface of the adsorbent carry positive charges. Rhodamine B is a cationic coloring agent and also mainly exists in cationic form under acidic conditions. Due to electrostatic attraction, the interaction force between magnetic composite materials and rhodamine B molecules increases, thereby increasing the adsorption capacity. Adsorption kinetics of rhodamine B with samples In the research, the pseudo-first-order kinetic model, pseudo-second-order kinetic model, Elovich model and Weber-Morris intraparticle diffusion model, and provided fitting diagrams and relevant fitting parameters (Fig. 6 A, 6 B, 6 C, 6 D and Table S2) were used to evaluate adsorption kinetics processes. It reveals that the optimal correlation exists between the pseudo-second-order equation and the obtained outcome, indicating that the adsorption models of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 for rhodamine B are more inclined to the pseudo-second-order kinetic model. Meanwhile, chemical adsorption takes the leading role (Jiang et al. 2019 ). As demonstrated in the Fig. 6 A and 6 C, the correlation between reaction time and adsorption capacity is presented. The adsorption amount keeps increasing as the reaction time lengthens, reaching a state of equilibrium when the reaction concludes. At the start of the experiment, the growth of removal ability is associated with plentiful adsorption vacant sites. But the saturation of these adsorption sites occurs progressively, resulting in the decline of the adsorption capacity(Wei et al. 2022a ). The pseudo-second-order kinetic model is better with fitting data. The Elovich model postulates that the adsorbent active sites are non-uniform, and shows diverse activation energies for the adsorption of organics (Zhao et al. 2017 ). In addition, through the Elovich model parameter (1/a), the stability of the adsorption process can also be analyzed. The smaller 1/a is, the more stable the adsorption process is. Therefore, the adsorption stability of Fe 3 O 4 -OTTP-1 (1/a = 0.2886) is greater than that of Fe 3 O 4 -OTTP-2 (1/a = 12.5786). The Elovich model can reflect the rate change in the adsorption process. Generally speaking, as the adsorption proceeds, the adsorption rate may gradually decrease, which is associated with how saturated the adsorption sites are. The adsorption capacity obtained from the experiment is very approximate the theoretical value forecasted by the model. These discoveries indicate that the adsorption course fully follows the Elovich model. Through the analysis of the Weber-Morris intraparticle diffusion model, we can deeply understand the diffusion of adsorbates inside the adsorbent particles and provide an important foundation for study of the adsorption process mechanism and the design of adsorbents. Since the intraparticle diffusion model is capable of fitting the experimental data effectively and the intraparticle diffusion rate is relatively fast in the entire adsorption process, it implies that intraparticle diffusion may be limiting the rate of removal, that is, the diffusion of rhodamine B inside the particles of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 controls the adsorption rate(Zhiyuan Liu et al. 2024b ). Adsorption isotherm of rhodamine B with samples Adsorption isotherm is a curve that depicts the association between the adsorption amount of adsorbent to adsorbate and the equilibrium at a certain temperature. In this work, different isotherm models are used to understand the relevant fitting parameters (as depicted in the Fig. 6 E-F and Table S3). The Langmuir adsorption isotherm successfully describes that adsorbed molecules and adsorption sites exhibit monolayer adsorption. In contrast to the Langmuir isotherm, the Freundlich isotherm is frequently utilized to depict multilayer adsorption taking place on non-uniform surface. Table S3 shows that the fitting coefficient of the Langmuir adsorption isotherm exceeds that of the Freundlich isotherm, indicating that the removal of rhodamine B occurs uniformly on the surface of magnetic materials and this kind of adsorption is single-layer adsorption. The effectiveness of the adsorption reaction is evaluated by the Langmuir adsorption model parameter R L (R L = 1/ (1 + KC 0 )). When 0 < R L < 1, it indicates that the process is advantageous (Shehzad et al. 2019 ). Through calculation, it is proved that the adsorption processes of Fe 3 O 4 -OTTP-1 (R L = 0.1836) and Fe 3 O 4 -OTTP-2 (R L = 0.3658) are favorable. The parameter n of the Freundlich isotherm reflects the adsorption strength or the affinity between the adsorbent and the adsorbate. Fe 3 O 4 -OTTP-1 (n = 0.6649) and Fe 3 O 4 -OTTP-2 (n = 0.4390) have good adsorption-desorption capabilities, providing a underpinning for the recycling of materials(Aghaei et al. 2023 ). The Sips adsorption model is an adsorption model that combines the features of the Langmuir model and the Freundlich model. When n s = 1, the Sips model degenerates into the Langmuir model, when n s approaches 0, the Sips model is close to the Freundlich model(Zhen Wu et al. 2017b ). And Fe 3 O 4 -OTTP-1 (n s = 0.6895) and Fe 3 O 4 -OTTP-2 (n s = 0.6217) are both nearly 1, signifying that the adsorption process of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 for rhodamine B is ideal monolayer adsorption. An empirical adsorption model, the Toth adsorption model is used to describe the behavior of the adsorbents. The value of K T of Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 is relatively small, which indicates that the compatibility of the adsorbent to the adsorbate is weak(Kumar et al. 2020 ), which is consistent with the results obtained from the Freundlich isotherm. The XPS spectra of samples (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2) adsorbed rhodamine B The XPS spectra were performed to confirm rhodamine B adsorption state on surface of magnetic inorganic/organic hybrid materials, and the results are shown in Fig. 7 A-E. In the Fe 3 O 4 -OTTP-1 sample, the content of C = C bond is 70.92% and the content of C = N bond is 29.08% respectively. After adsorbed rhodamine B in the Fe 3 O 4 -OTTP-1 sample, the content of C = C bond is 90.15% and the content of C = N bond is 8.85%. And in the Fe 3 O 4 -OTTP-2 sample, the content of C = C bond is 70.54% and the content of C = N bond is 29.46% respectively. After adsorbed rhodamine B in the Fe 3 O 4 -OTTP-2 sample, the content of C = C bond is 72.32% and the content of C = N bond is 27.68%. These results demonstrate that the removal rhodamine B ability of Fe 3 O 4 -OTTP-1 is better than that of Fe 3 O 4 -OTTP-2, which is consistent with the adsorption kinetics experimental results. It is precisely due to the π-electron interaction between Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2 and rhodamine B, and the content of C-C/C = C becomes greater. After rhodamine B were absorbed by samples (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2), FTIR and XRD characterizations were performed for confirming adsorption state (Fig. 7 F-G). There are several peaks at 3201 cm − 1 , 1700 cm − 1 and 1487 cm − 1 , which are attributed to the stretching vibrations of benzene rings and other aromatic ring structures in the molecular structure of rhodamine B, the extensional vibrations of -COOH, and the stretching oscillation of C-H bonds on benzene rings and hydrogen atoms on other unsaturated carbons. The XRD patterns are shown in Fig. 7 -R, it is not new phases discovering after adsorbed rhodamine B, which indicates that adsorption does not have an adverse effect on the magnetic composite material. Regeneration of samples (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2) In general, absorbents can be regenerated by thermal regeneration method(Hak-Hyeon Kim et al. 2024 ), vacuum regeneration method(Yongbiao et al. 2024 ), chemical regeneration method(Moxi and Xue-yi 2021 ) and electrochemical regeneration method(Yasri and Roberts 2024 ). The thermal regeneration method possesses some advantages, such as simple operation, stable regeneration effect and environmental friendliness. In this experiment, the thermal regeneration temperature is selected 200°C and the regeneration holding-time is selected 3 hours. After the adsorption reaction is completed, the adsorbent is separated by an external magnet and then subjected to heat treatment for the regeneration experiment. The regeneration performance of samples (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2) is shown in Fig. 8 . After four adsorption-thermal regeneration cycles, the adsorption rate of Fe 3 O 4 -OTTP-1 is 26.80% and the adsorption rate of Fe 3 O 4 -OTTP-2 is 25.02%. It can be seen that the adsorption capability of materials (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2) decrease with the adsorption-thermal regeneration cycles increasing, a possible explain is the microstructure destruction of inorganic/organic hybrid materials. Moreover, the surface functional groups of samples happen thermal decomposition or chemical reactions, lead to surface active adsorption sites decreasing. At the same time, some rhodamine B molecules still remain inside the magnetic schiff base composite material, and rhodamine B molecules of solution is difficult to adsorb on surface active sites of magnetic complicate materials. Calculation based on theory and mechanism In order to understand the π-π interaction in rhodamine B molecules adsorption processes, theoretical calculations were performed during the implementation of this work. Here, density functional calculations (DFT) are mainly performed through several aspects such as structure optimization, monomer energy calculation, combination energy calculation, analytical visualization of molecular orbitals and electrostatic potential diagrams. The calculation of monomer energy and binding energy is carried out on the basis of structure optimization. Figure 9 A-E are the structure optimization diagrams of OTTP and rhodamine B respectively. Among the molecular orbitals, the uppermost occupied molecular orbital (HOMO) and the lowermost unoccupied molecular orbital (LUMO) play important roles for molecular properties. In the analytical visualization of molecular orbitals, HOMO orbital and LUMO orbital are selected for analysis(Lin et al. 2024 ). Figure 9 B-D are the HOMO orbital, the LUMO orbital and the electrostatic potential diagrams of Fe3O4-OTTP respectively. Figure 9 F-H are the HUMO orbital, the LUMO orbital and the electrostatic potential diagrams of rhodamine B respectively. If there are differences in the LUMO and HOMO molecular orbital diagrams of two reactants, it is considered that there is an electron donor-acceptor interaction. Generally, Fe3O4-OTTP hybrids materials act as electron donor, and rhodamine B act as an electron acceptor. Furthermore, the steadiness of charge distribution during the adsorption process is studied through the characteristics of electrostatic potential distribution. The distribution of positive and negative electrostatic potential regions in the system are shown in Fig. 9 -H. The blue regions represent that they are relatively electron-deficient and have a positive electrostatic potential, and the potential electron acceptor regions show stronger electrophilicity relative to other regions. Meanwhile, the negative electrostatic potential regions (red regions) indicate that they are relatively electron-rich and may be potential electron donor regions or are more nucleophilic than other regions(Mabkhot et al. 2017 ; Vijay et al. 2019 ). Calculation results show that the charge distribution of Fe 3 O 4 -OTTP is close to neutral, and the electrostatic potential of rhodamine B is tendency to negative potential. The combination energy (ΔE) of Fe 3 O 4 -OTTP and rhodamine B molecules in the context of numerous stacking modes, calculations of the combination energy (ΔE) can be made by means of the following formula: ΔE = E (Fe3O4−OTTP···rhodamine B) – E (Fe3O4−OTTP) – E (rhodamine B) wher e E (Fe3O4−OTTP···rhodamine B) , E (Fe3O4−OTTP) and E (rhodamine B) correspond to the energies of the optimized Fe 3 O 4 -OTTP···rhodamine B, Fe 3 O 4 -OTTP and rhodamine B structures respectively. Due to the large size of rhodamine B molecules, errors may occur during calculation. Therefore, five stacking methods with smaller errors are proposed to calculate their binding energy. During the process of setting the stacking mode, the distance between the aromatic rings in Fe 3 O 4 -OTTP and rhodamine B molecules is set to 3 Å. First, these five stacking modes are optimized. The optimized structures are shown in Fig. 10 A-Q, and the distances between C-C in the aromatic rings are shown in Table S4. The binding energies corresponding to the five stacking modes are listed in Table S5. The total energies of the five magnetic materials and rhodamine B are ranked as V (-2915.817720 a.u) < III (-2915.816619 a.u) < IV (-2915.807424 a.u) < II (-2915.802948 a.u) < I (-2915.790560 a.u), and the arrangement order of ΔE (a.u) values is also V (-0.044045 a.u) < III (-0.042944 a.u) < IV (-0.033749 a.u) < II (-0.029273 a.u) < I (-0.016885 a.u). These calculation results indicate that the best bonding mode simulated during the adsorption process is type I. It can be found that the HOMO and LUMO orbits of Fe 3 O 4 -OTTP change (as shown in Fig. 10 B, 10 C, 10 F, 10 G, 10 J, 10 K, 10 N, 10 O, 10 R, and 10 S) in the rhodamine B adsorption processes, indicating that rhodamine B has been adsorbed on the magnetic inorganic/organic hybrid materials. In addition, after rhodamine B adsorption, the E GAP (E GAP = E LUMO - E HOMO ) value also changes, indicating that the electron donor-acceptor interaction between molecules may be affected during the adsorption process, thereby affecting the stability of adsorption. Figure 10 D, 10 H, 10 L, 10 P, and 10 T are electrostatic potential diagrams under five different stacking modes. It can be seen that after adsorption, the five stacking modes show cationic characteristics and negative potential distribution. In light of experimental and theoretical analysis, the main principle about the adsorption process is summarized in Fig. S3. In the start of adsorption, rhodamine B molecules reach the outer surface of the magnetic Schiff base composite material through membrane diffusion, and then reach the inner surface of the magnetic schiff base composite material through internal diffusion. Subsequently, rhodamine B molecules are effectively adhered to Fe 3 O 4 -OTTP-1 and Fe 3 O 4 -OTTP-2 through chemical interactions, such as the π-π stacking interaction, the interaction between electron donor and acceptor. Finally, the adsorption processes reach the equilibrium state because the active sites have been absorbed rhodamine B molecules. Simultaneously, the additional interaction between rhodamine B molecules and magnetic composite materials come from other forces including van der Waals force, hydrophobic interaction and electrostatic attraction(Youwen et al. 2022 ). Conclusions In this paper, magnetic inorganic/organic hybrid materials (Fe 3 O 4 -OTTP-1, Fe 3 O 4 -OTTP-2) were prepared by situ polymerization method from o-Tolidine and p-phthalaldehyde. Schiff base polymer shells provide numerous active sites for rhodamine B adsorption, and Fe 3 O 4 magnetic cores of the inorganic/organic hybrid materials separated the adsorbed rhodamine B from wastewater easily. The following conclusions can be drawn. (1) Magnetic inorganic/organic hybrid materials (Fe3O4-OTTP-1, Fe 3 O 4 -OTTP-2) possess excellent rhodamine B adsorption capability, these magnetic core-shell hybrid materials have potential application in organic dyes removing. (2) According to adsorption isotherm research, rhodamine B adsorption on magnetic inorganic/organic hybrid materials are consistent with the Langmuir adsorption model, indicating that homogeneous monolayer is formed in the adsorption processes. (3) According to theoretical calculations, the charge distribution of Fe 3 O 4 -OTTP is close to neutral, and the electrostatic potential of rhodamine B is tendency to negative potential. And in rhodamine B adsorption, the E GAP (E GAP = E LUMO - E HOMO ) value also changes, indicating that the electron donor-acceptor interaction can be affected during the adsorption process. Declarations Acknowledgements ： This work was supported by the National Natural Science Foundation of China (51678059，42407081), the Fundamental Research Funds for the Central Universities, CHD (300203211293), the Innovative Research Team for Science and Technology of Shaanxi Province (2022TD-04), the Postdoctoral Fellowship Program of CPSF under Grant Number (GZC20232222). Author contributions Liuqing Li: Experimental design, carrying out measurements and manuscript write. Zhengwen Wei: Conception, manuscript revision. Zhenyi Jiang: Theoretical calculations. Xiangfei Lv: Characterization data analysis. Wei Wang: Conception, experimental design. Conflicts of interest or competing interests The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. Data and code availability All data included in this study are available upon request by contact with the corresponding author. 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Journal of Hazardous Materials, 403:123810. https://doi.org/10.1016/j.jhazmat.2020.123810 Supplementary Files SupplementaryMaterial1.doc Cite Share Download PDF Status: Published Journal Publication published 29 Oct, 2025 Read the published version in Chemical Papers → Version 1 posted Reviewers agreed at journal 09 Jul, 2025 Reviewers invited by journal 09 Jul, 2025 Editor invited by journal 30 Jun, 2025 Editor assigned by journal 26 May, 2025 First submitted to journal 23 May, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-6728589","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":483070427,"identity":"8e3ef15e-a961-4d61-8edc-f814f3d02337","order_by":0,"name":"Liuqing Li","email":"","orcid":"","institution":"Changan University: Chang'an University","correspondingAuthor":false,"prefix":"","firstName":"Liuqing","middleName":"","lastName":"Li","suffix":""},{"id":483070428,"identity":"88603135-5a1f-44a9-9e2b-7537fc1e47a1","order_by":1,"name":"Zhengwen Wei","email":"","orcid":"","institution":"Changan University: Chang'an University","correspondingAuthor":false,"prefix":"","firstName":"Zhengwen","middleName":"","lastName":"Wei","suffix":""},{"id":483070429,"identity":"40537e7d-187f-4baf-a53d-96e6ff44560f","order_by":2,"name":"Xiang-fei Lü","email":"","orcid":"","institution":"Changan University: Chang'an University","correspondingAuthor":false,"prefix":"","firstName":"Xiang-fei","middleName":"","lastName":"Lü","suffix":""},{"id":483070430,"identity":"b114bf0d-3ef0-4b58-8510-149aeaa39570","order_by":3,"name":"Zhen-Yi Jiang","email":"","orcid":"","institution":"Changan University: Chang'an University","correspondingAuthor":false,"prefix":"","firstName":"Zhen-Yi","middleName":"","lastName":"Jiang","suffix":""},{"id":483070431,"identity":"35940df6-8f52-43ed-9466-93e62d447bb7","order_by":4,"name":"Wei Wang","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAoUlEQVRIiWNgGAWjYHACNiC24eFnbyBNS5qMZM8B0rQctjG44UCkeoMbyc8efMw5z8Nwg4Hxw8ccorSkmRvO3Habh3F2A7PkzG1EaDG7ncMmzQvUwixzgI2Zl2gtf7ed42GTSCBFC+O2Azw8RGuxv//MTLJ3WzKPBM/BZuL8Itlz+JnEz2129vbHmw9++EiMFiTA2ECa+lEwCkbBKBgFuAEAe7sz4w0MSCYAAAAASUVORK5CYII=","orcid":"https://orcid.org/0000-0002-0540-1810","institution":"Chang'an University","correspondingAuthor":true,"prefix":"","firstName":"Wei","middleName":"","lastName":"Wang","suffix":""}],"badges":[],"createdAt":"2025-05-23 02:30:52","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-6728589/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-6728589/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1007/s11696-025-04436-3","type":"published","date":"2025-10-29T15:58:29+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":86696827,"identity":"b82f3f2c-a883-45f2-bf42-08a9098c3844","added_by":"auto","created_at":"2025-07-14 15:34:04","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":4878856,"visible":true,"origin":"","legend":"\u003cp\u003eSEM images of (A) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, (B) OTTP, (C) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and (D) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2; Electronic elemental images of (E) OTTP, (I) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and (N) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2; Distribution maps of C, N, and O elements of OTTP (F-H), Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (G-L) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (O-Q); Distribution map of Fe element of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (M) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (R); Surface element distribution of OTTP (S), Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (T) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (U).\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/db59bb4c7dfc37ddd9cb9cdf.png"},{"id":86696277,"identity":"fa514cef-2c5a-4b1a-ba82-9de2b26cf562","added_by":"auto","created_at":"2025-07-14 15:26:04","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":1020865,"visible":true,"origin":"","legend":"\u003cp\u003e(A) Overall XPS survey of OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2; C1s spectra of (B) OTTP, (E)Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and (I) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2; N1S spectra of (C) OTTP, (F) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and (G) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2; O1S spectra of (D) OTTP, (G) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and (K) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2; Fe 2p spectra of (H) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and (L) Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2.\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/fc6805940bb9791487fd767c.png"},{"id":86696282,"identity":"970d4e39-9581-4c99-b482-1530019f9e57","added_by":"auto","created_at":"2025-07-14 15:26:04","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":566982,"visible":true,"origin":"","legend":"\u003cp\u003eGPC curve (A, B) of OTTP, (C) Magnetic curves, (D) FTIR spectrums, (E) XRD patterns, (F) N\u003csub\u003e2\u003c/sub\u003e adsorption desorption isotherms and (G) Pore size curves of different materials.\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/6915309ebef380650460e9d7.png"},{"id":86697528,"identity":"46a21702-1f35-44c1-bd07-a03084a9b656","added_by":"auto","created_at":"2025-07-14 15:42:04","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":156267,"visible":true,"origin":"","legend":"\u003cp\u003e1H NMR spectra of (A) O-Tolidine, (B) p-phthalaldehyde (C) OTTP.\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/ab1a6100eaf64694cc9b9640.png"},{"id":86696828,"identity":"9e0db47d-17b4-4873-b85f-cea7522a055b","added_by":"auto","created_at":"2025-07-14 15:34:04","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":767088,"visible":true,"origin":"","legend":"\u003cp\u003e(A)\u003cstrong\u003e \u003c/strong\u003eComparison of rhodamine B removal properties of different nanomaterials; effects of (B) temperature, (C) adsorbent dosage and (D) pH on the adsorption performance of rhodamine B.\u003c/p\u003e","description":"","filename":"5.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/e8cf4abf8e40410db6ba950d.png"},{"id":86696284,"identity":"0dc65fa1-6dd9-454d-ac41-ad81f03d7660","added_by":"auto","created_at":"2025-07-14 15:26:04","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":4060490,"visible":true,"origin":"","legend":"\u003cp\u003eFirst-order kinetic model, pseudo-second-order kinetic model, and Elovich model of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1(A) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2(C); Intraparticle diffusion model of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1(B) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2(D); adsorption isotherms of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1(E) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2(F).\u003c/p\u003e","description":"","filename":"6.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/6a4767b8549476d1d965f01e.png"},{"id":86696831,"identity":"4c55dba4-256a-40de-8772-f027a3717c29","added_by":"auto","created_at":"2025-07-14 15:34:04","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":7803948,"visible":true,"origin":"","legend":"\u003cp\u003e(A) Overall XPS survey of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 ,Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 after rhodamine B adsorption; (B) C 1s spectra for Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1; (C) C 1s spectra for Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 after rhodamine B adsorption; (D) C 1s spectra for Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2; (E) C 1s spectra for Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 after rhodamine B adsorption; (F) FTIR spectrum of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 before and after after rhodamine B adsorption; (G) FTIR spectrum of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 before and after after rhodamine B adsorption.\u003c/p\u003e","description":"","filename":"7.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/e4060d84267f2f78010b8b61.png"},{"id":86696829,"identity":"b7e5abc3-e417-44a5-bcb5-52004a54367d","added_by":"auto","created_at":"2025-07-14 15:34:04","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":2316589,"visible":true,"origin":"","legend":"\u003cp\u003eRegeneration performance of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (A) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (B)\u003c/p\u003e","description":"","filename":"8.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/32496ab1f8e5d6855532e464.png"},{"id":86696289,"identity":"a5d9cc94-8593-4e6e-884e-97e0f20ea54b","added_by":"auto","created_at":"2025-07-14 15:26:04","extension":"png","order_by":9,"title":"Figure 9","display":"","copyAsset":false,"role":"figure","size":894089,"visible":true,"origin":"","legend":"\u003cp\u003eThe optimized structures of Fe3O4-OTTP (A) and rhodamine B (E); the LUMO (B) and HUMO (C) orbitals of Fe3O4-OTTP; the LUMO (F) and HUMO (G) orbitals of rhodamine B; and the electrostatic potential diagrams of Fe3O4-OTTP (D) and rhodamine B (K).\u003c/p\u003e","description":"","filename":"9.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/4bf24141e1d8fd5b33c1244e.png"},{"id":86696297,"identity":"cda48af7-3e6b-458d-878f-d0214ebc7c2c","added_by":"auto","created_at":"2025-07-14 15:26:04","extension":"png","order_by":10,"title":"Figure 10","display":"","copyAsset":false,"role":"figure","size":2699292,"visible":true,"origin":"","legend":"\u003cp\u003e(A), (E), (R), (M), and (Q) are the five bonding modes of I, II, III, VI, and V respectively; the HOMO (B) and LUMO (C) orbitals of I, the HOMO (F) and LUMO (G) orbitals of II, the HOMO (J) and LUMO (K) orbitals of III, the HOMO (N) and LUMO (O) orbitals of VI, and the HOMO (R) and LUMO (S) orbitals of V; (D), (H), (L), (P), and (T) are the electrostatic potential diagrams of I, II, III, VI, and V respectively.\u003c/p\u003e","description":"","filename":"10.png","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/92f780e838a4ae741e199a91.png"},{"id":95041454,"identity":"1310c2fb-b245-4a68-b828-af9cff0e5407","added_by":"auto","created_at":"2025-11-03 16:11:40","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":23610172,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/3644e881-ba15-4240-ae95-f46f20a49a93.pdf"},{"id":86696286,"identity":"84c83b5c-aace-4ba4-ab71-e6a8be8fa187","added_by":"auto","created_at":"2025-07-14 15:26:04","extension":"doc","order_by":4,"title":"","display":"","copyAsset":false,"role":"supplement","size":1888768,"visible":true,"origin":"","legend":"","description":"","filename":"SupplementaryMaterial1.doc","url":"https://assets-eu.researchsquare.com/files/rs-6728589/v1/79d657d779f7938ed18f07a3.doc"}],"financialInterests":"","formattedTitle":"Preparation of magnetic Schiff base nanocomposites for removal of Rhodamine B","fulltext":[{"header":"Introduction","content":"\u003cp\u003eIn the last decades, with the rapid development of the economy, environmental pollution problems have become great challenges for the sustainable development of society(Cao et al. \u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e2023\u003c/span\u003e; Kazem et al. \u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e2025\u003c/span\u003e; Ting-Ting Liu et al. \u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e2024a\u003c/span\u003e). Different organic pollutants, such as organic dyes, antibiotics, cosmetics and food additives, have been detected in environmental samples(Jain et al. \u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e2018\u003c/span\u003e; Kaur et al. \u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). These organic pollutants are not only difficult to degrade naturally, but also lead to the serious environmental disasters(Sudhamayee et al. \u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e2025\u003c/span\u003e; Xiao-Qian et al. \u003cspan citationid=\"CR51\" class=\"CitationRef\"\u003e2025\u003c/span\u003e). Organic pollutants have the characteristics of poor biodegradability, high toxicity, teratogenicity, thus which not only affects the aesthetics of the environment but also does harm to human body(Okpara et al. \u003cspan citationid=\"CR31\" class=\"CitationRef\"\u003e2024\u003c/span\u003e). Rhodamine B is a kind of triphenylmethane alkaline water-soluble organic dye with fresh peach color, which is used in the textile industry, colored glass, and other industries(Nilmadhab et al. \u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e2025\u003c/span\u003e). For the treatment of rhodamine B wastewater, several techniques, such as photolysis(Pooja et al. \u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e2025\u003c/span\u003e), electrocatalytic oxidation(Yitong et al. \u003cspan citationid=\"CR54\" class=\"CitationRef\"\u003e2025\u003c/span\u003e), biological treatments(Kashama et al. \u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e2025\u003c/span\u003e) and advanced oxidation(Phuong Hoang et al. \u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e2024\u003c/span\u003e) have been used to eliminate organic pollutants effluents.\u003c/p\u003e\u003cp\u003ePhotocatalytic degradation of rhodamine B has been extensively investigated for green and environmentally friendly features in the last decades. However, the shortcomings of photocatalytic degradation, such as insufficient adsorption capacity, secondary pollution, speedy recombination of photogenerated electrons and holes and inferior migration capacity still restrict the application of photocatalytic technology (Kavya et al. \u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e2021\u003c/span\u003e; Yan et al. \u003cspan citationid=\"CR52\" class=\"CitationRef\"\u003e2024\u003c/span\u003e). Advanced oxidation is the organic pollutants treatment technique that utilizes strong oxidizing substances (ozone, hydroxyl radicals, etc.) to react with dissolved pollutants in wastewater to degrade the organic molecular structure(Miaomiao et al. \u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e2025\u003c/span\u003e). It is inevitable to introduce some chemical reagents in system for strong oxidizing substances production while to use the advanced oxidation technology(Qiufeng et al. \u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e2024\u003c/span\u003e). Electrocatalytic oxidation refers to the electrode, electrolyte interface charge transfer to accelerate the reaction of catalytic oxidation, which can effectively reduce the activation energy of the interfacial electric field reaction system to promote the reaction so that the organic pollutants in the anode are rapidly degraded(Wenxuan et al. \u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e2025\u003c/span\u003e). Biological treatment method is a cost-effective and environmentally friendly approach to eliminate organic pollutants, and this technique benefits greatly from the flexibility of numerous microorganisms in degrading various compounds. However, organic pollutants effluents are poor in nutrients, consequently, nutritional supplements (such as nitrogen, carbon and phosphorus sources) are often necessary to improve treatment effect(Bornali et al. \u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e2025\u003c/span\u003e).\u003c/p\u003e\u003cp\u003eIn numerous treatment technologies, adsorption, a method of removing organic pollutants by adsorbents, is widely utilized because of its favorable efficiency and easy operation(Ruisi Qiu et al. \u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e2024b\u003c/span\u003e). The adsorbents for rhodamine B include biochar materials(Behera et al. \u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2024\u003c/span\u003e), organic-inorganic nanomaterials(Yuan et al. \u003cspan citationid=\"CR57\" class=\"CitationRef\"\u003e2024\u003c/span\u003e), organic skeleton materials (Terr\u0026oacute;n et al. \u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e2024\u003c/span\u003e)etc. However, the adsorbent is powder form in general, which increases comprehensive treatment processes(Chen Zhang et al. \u003cspan citationid=\"CR58\" class=\"CitationRef\"\u003e2020\u003c/span\u003e). And the rapid recovery treatment of water pollution adsorption materials has become a research hotspot in recent years(Saad et al. \u003cspan citationid=\"CR38\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). Due to easy separation, magnetic nanoparticles have been extensively researched for removal organic pollutants in wastewater. Ouyang et al. used magnetic materials to prepare Porous β-CD polymer (CDP) composite material to adsorb organic pollutants. The adsorbent has higher adsorption capacity and good reusability than previously reported materials(Jinya et al. \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e2023\u003c/span\u003e). Qiu et al. developed wood fiber loaded with nano-scale zero-valent iron to improve the magnetic and dye-degrading ability of wood fiber(Dongxu Qiu et al. \u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e2024a\u003c/span\u003e). Joshiba et al. prepared Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e@SiO\u003csub\u003e2\u003c/sub\u003e with pseudomonas fluorescens biomass in calcium alginate beads (MSAB) as the bioadsorbent to eliminate rhodamine B in water systems(Janet et al. \u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e\u003cp\u003eSchiff base is a kind of chemical substance which content the imine group (-C\u0026thinsp;=\u0026thinsp;N-)(Edyta et al. \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e2022\u003c/span\u003e), and the imine group provides a distinct function in generating these molecules with wide application in wastewater treatment(Xiaofei Zhang et al. \u003cspan citationid=\"CR59\" class=\"CitationRef\"\u003e2012\u003c/span\u003e). Moreover, Schiff base is easy to synthesize, and the aromaticity of Schiff base polymer will increase when the more aromaticity units is used in the synthesize processes, which will lead to the stronger π-π interactions between organic pollutants and Schiff base polymer(Zhengwen et al. \u003cspan citationid=\"CR62\" class=\"CitationRef\"\u003e2021\u003c/span\u003e). Pawariya et al. synthesized the chitosan-based Schiff base materials modified with citric acid with high efficiency capacity for dyes from wastewater(Pawariya et al. \u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e2024\u003c/span\u003e). Although magnetic nanoparticle complicated with Schiff base polymer to form magnetic hybrid materials has been researched somewhat, but not extensively over the adsorption removing mechanism on the density functional theory (DFT) calculation view.\u003c/p\u003e\u003cp\u003eIn this paper, magnetic Schiff base hybrid materials were prepared by situ polymerization method from o-Tolidine and p-phthalaldehyde. And Schiff base polymer molecular content plenty of benzene rings and naphthalene rings, increasing the π-π stacking interaction between rhodamine B and Schiff base polymer, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e magnetic cores of the inorganic/organic hybrid materials separated the adsorbed rhodamine B from wastewater easily. Density functional theory (DFT) was used to explore the adsorption energy, adsorption mode and adsorption mechanism.\u003c/p\u003e"},{"header":"Materials and methods","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e\u003ch2\u003eMaterials\u003c/h2\u003e\u003cp\u003eO-Tolidine (C\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e), p-phthalaldehyde (C\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e) and nano-ferric tetroxide (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e) were obtained from Aladdin Chemical Reagent Limited Company (Shanghai, China). Sodium dodecyl sulfate (CH\u003csub\u003e3\u003c/sub\u003e(CH\u003csub\u003e2\u003c/sub\u003e)\u003csub\u003e11\u003c/sub\u003eOSO\u003csub\u003e3\u003c/sub\u003eNa) was bought from Damao Chemical Reagent Limited Company (Tianjin China). Rhodamine B (C\u003csub\u003e28\u003c/sub\u003eH\u003csub\u003e31\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e) was bought from Fuchen Chemical Reagent Limited Company (Tianjin China). Nitric Acid (HNO\u003csub\u003e3\u003c/sub\u003e, 65\u0026ndash;68 wt%), sodium hydroxide (NaOH) and ethanol (C₂H₅OH) were supplied by Xian Chemical Reagent Factory (Xi\u0026rsquo;an China).\u003c/p\u003e\u003c/div\u003e\n\u003ch3\u003eMagnetic composite materials preparation\u003c/h3\u003e\n\u003cp\u003eThe polycondensation reaction pathway diagram from o-tolidine and p-phthalaldehyde is shown in Fig. \u003cspan refid=\"MOESM1\" class=\"InternalRef\"\u003eS1\u003c/span\u003e. The flow chart of magnetic composite materials preparation is shown in Fig. S2. The specific preparation processes are described as follows. Magnetic schiff base inorganic/organic hybrid materials were synthesized by one-pot embedding method. Firstly, 0.335 g of p-phthalaldehyde was dissolved in 40 mL anhydrous ethanol named solution A, and 0.53 g of o-tolidine was dissolved in 40 mL anhydrous ethanol named solution B. Secondly, Solution A was mixed with solution B at 25\u0026deg;C for 24 hours continuously stirring. Then, yellow sediments were formed in this stage. Finally, Schiff base polymers (OTTP) were obtained after filtration, washing and drying.\u003c/p\u003e\u003cp\u003eMagnetic inorganic/organic hybrid materials were prepared through two synthetic pathways. Nano-ferric tetroxide was weighed 0.65g accurately and suspended in 40 mL deionized water to form the suspension A. Subsequently, 0.2 g of OTTP and 0.25 g of sodium dodecyl sulfate were suspended in 100 mL deionized water, the suspension B was formed after adjusting (2M HNO\u003csub\u003e3\u003c/sub\u003e) the pH to 2. Then, suspension A was mixed with suspension B at room temperature and stirred 3 hours. Finally, the magnetic hybrid materials (named Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1) was prepared after magnetic separation, washing and drying.\u003c/p\u003e\u003cp\u003eAnother synthetic pathway of magnetic inorganic/organic hybrid materials is the situ condensation reaction. Firstly, 0.15 g of p-phthalaldehyde was dissolved in 50 mL anhydrous ethanol named solution A, and 0.05 g of o-tolidine was dissolved in 50 mL anhydrous ethanol named solution B. Subsequently, nano-ferric tetroxide was weighed 0.325 g accurately and suspended in 50 mL anhydrous ethanol to form the suspension C. Then, solution A and solution B were added into suspension C with continuously stirred 3 hours at room temperature. Finally, the magnetic hybrid materials (named Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) was prepared after magnetic separation, washing and drying.\u003c/p\u003e\n\u003ch3\u003eCharacterization\u003c/h3\u003e\n\u003cp\u003eSamples were analyzed by Fourier transform infrared (FT-IR) using Nicolet 5700 analyzer. X-ray photoelectron spectroscopy (XPS) instrument (ESCALB Xi\u003csup\u003e+\u003c/sup\u003e) was used to determine the elements on the surface of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2. X-ray diffraction analyzer (XRD, D8 ADVANCE) was used to research phase and composition of magnetic hybrid materials. The microscopic morphology and element composition of the sample was measured by scanning electron microscope (SEM, S-4800, Hitachi, Japan), equipped with an energy dispersive spectrometer (EDS, INCA-350, Oxford, UK). Transmission electron microscope (TEM, JEM-2100F) was applied to detect the microstructures. The hysteresis loop of samples was performed by the vibrating sample magnetometer (VSM, LAKE 7404). The pore size distribution of the samples was carried out by Brunauer, Emmett and Teller (BET, NOVA 2000, USA). Nuclear Magnetic Resonance (NMR, AVANCE NEO 400MHZ) was used to determine the hydrogen spectrum of samples. The gel permeation chromatography (GPC) experiment was carried out on an Agilent PL-GPC50 analyzer to estimate the average molecular weight.\u003c/p\u003e\n\u003ch3\u003eBatch adsorption experiments\u003c/h3\u003e\n\u003cp\u003eThe absorption behavior of samples for rhodamine B was assessed in batch experiments under different conditions. In the kinetic adsorption experiment, rhodamine B solution was obtained by dissolving 30 mg rhodamine B in 1 L deionized water, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (or Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) were weighed 0.14g accurately and placed into 210 mL rhodamine B solution (30 mg/L) respectively, and shaking adsorption reaction for 6 h. The mixed solutions were magnetically separated with different adsorption time. In particular, the supernatant is filtered through a microporous membrane to reduce experimental error. The concentration of rhodamine B were detected by the L6S ultraviolet-visible spectrophotometer, and the adsorption capacity of materials were calculated. The adsorption experiments were repeated three times for decreasing errors, and every data were the arithmetic mean. In the isotherm experiment, 0.02g Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (or Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) was put into different concentration rhodamine B solution (30 mL) to research thermodynamic process of adsorption. Moreover, the removal performance in relation to different temperature, pH, and adsorbent dosage were investigated as well. Finally, adsorbed Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 were separated from the mixed solution and washed by anhydrous ethanol three times. It was pyrolyzed at 200\u0026deg;C for 3 h and used in the subsequent adsorption reaction for cyclic performance investigation.\u003c/p\u003e\n\u003ch3\u003eTheory calculation\u003c/h3\u003e\n\u003cp\u003eTheoretical calculation was conducted using GAUSSIAN 16 software. The molecular structure of rhodamine B, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 were optimized by B3 LYP-D3 method(Zirong Zhang and Collum \u003cspan citationid=\"CR60\" class=\"CitationRef\"\u003e2018\u003c/span\u003e), and the base group 6-311G(d,p) was selected for fast optimization(Tian et al. \u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e2018\u003c/span\u003e; Zhu et al. \u003cspan citationid=\"CR63\" class=\"CitationRef\"\u003e2020\u003c/span\u003e). The bonding mode of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 with rhodamine B were also optimized by this method. In addition, the M062X-D3 method was utilized to calculate molecular monomer energy, and the M062X-D3-group superposition correction factor was used to calculate the bonding energy, and the group was selected 6-311G+(d,p)(Junhong Wu et al. \u003cspan citationid=\"CR49\" class=\"CitationRef\"\u003e2017a\u003c/span\u003e). It is important to note that for the purpose of improving the computational speed and precision of the results, we choose the partial aromatic carbon of rhodamine B for theoretical calculation. In order to analyze the properties of bonding modes, the distribution of molecular orbitals and electrostatic potentials are also obtained(Wei et al. \u003cspan citationid=\"CR46\" class=\"CitationRef\"\u003e2022a\u003c/span\u003e).\u003c/p\u003e"},{"header":"Results and Discussion","content":"\u003cdiv id=\"Sec9\" class=\"Section2\"\u003e\n \u003ch2\u003eFe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 Characterization\u003c/h2\u003e\n \u003cp\u003eSurface morphologies of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 are shown in Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e(A-D). Diameter of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nanoparticles is about 20 nm, and the aggregation of nanoparticles take place due to the magnetic forces between particles. OTTP has a three-dimensional micron sheet structure, and these microstructure makes the possesses of inorganic-organic encapsulation is more likely to occur. The SEM image of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 shows that organic molecular chains play the role of a bridge connection, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nanoparticles composite with polymer blocks using the intermolecular force. The SEM image of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 shows that Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e is encapsulated completely by the Schiff base polymer OTTP, and outside polymer molecular chains could provide more aromatic groups which is benefit for rhodamine B adsorption and removing. The element mapping images corresponding to the scanning electron micrographs of OTTP are shown in Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e(E-H), the elements of C, N, and O can be seen in the whole area, indicating that polymers have uniformity and high purity. The element of C, N, and O are detected in the mapping images of sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 in Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e(I-M), and the Fe element is observed simultaneously, indicating that Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nanoparticles are successfully embedded in the Schiff base polymer. Figure \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e(N-R) is the mapping images of sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2, and these mapping images are similar with sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, signals of C, N, O and Fe are also measured in the final inorganic/organic hybrid materials. Furthermore, by comparing the EDS schematic diagrams of OTTP (Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003eS), Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1(Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003eT), and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2(Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003eU), it can be seen that the content of element O in inorganic/organic hybrid materials (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2).\u003c/p\u003e\n \u003cp\u003eThe surface chemical composition and valence state of samples (OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) were analyzed by XPS technology. The XPS spectra of OTTP (Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eA) show that the peak corresponding to the C element appears at 284 eV, the peak is scribed to the N element appears at 398 eV, and the peak is attributed to the O element appears at 531.5 eV. Meanwhile, with regard to the XPS spectra of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2, it is noticed that not only are the C, N and O elements present, but also the characteristic peak corresponding to the Fe element is detected at 711 eV. Moreover, the high-resolution spectra of elements are used to obtain more comprehensive information, the C1s spectra of OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 are shown in Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eB, Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eE and Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eH respectively. The peak (284.4 eV) is originated from C\u0026thinsp;=\u0026thinsp;C/C-C (Khan et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e) and the peak (286.5 eV) is ascribed to C\u0026thinsp;=\u0026thinsp;N (Wei et al. \u003cspan class=\"CitationRef\"\u003e2022b\u003c/span\u003e) respectively. The N1s spectra of OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 are shown in Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eC, Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eF, and Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eG. Two peaks are found at 379.71 and 401.09 eV respectively, corresponding to N-C and N\u0026thinsp;=\u0026thinsp;C bonds(Shi et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e). Figure \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eD, Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eG, and Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eK are the O1s spectra of OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2, and which are attributed to O\u0026thinsp;=\u0026thinsp;C(Khan et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e) bond and O-H bond at 379.71 and 531.17 eV respectively. The characteristic peak appearing at 529.8 eV is ascribed to the O-Fe bond (Khan et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e) in Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eK. The Fe 2p spectrum (Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eH) has three peaks at 708.21, 709.10, and 725.51 eV, correlating to Fe\u003csup\u003e2+\u003c/sup\u003e 2p\u003csub\u003e3/2\u003c/sub\u003e, Fe\u003csup\u003e3+\u003c/sup\u003e 2p\u003csub\u003e3/2\u003c/sub\u003e, and Fe\u003csup\u003e3+\u003c/sup\u003e 2p\u003csub\u003e1/2\u003c/sub\u003e respectively. In addition, the three satellite peaks at 711.99 eV, 717.7 eV, and 731.32 eV confirm that the iron oxide is Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e. The distinctive azomethine (N\u0026thinsp;=\u0026thinsp;C) group indicates the effectiveness of the polycondensation reaction of Schiff base polymer synthesis, on the other hand, the aromatic carbon associated with the C\u0026thinsp;=\u0026thinsp;C/C-C group can provide the possibility of adsorbing rhodamine B through the \u0026pi;-\u0026pi; interaction.\u003c/p\u003e\n \u003cp\u003eThe distribution of the molecular weight of the OTTP polymer is shown in Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eA. It can be seen that the molecular weight of OTTP present relatively narrow peak in the curve, indicating that homogeneous molecular chains have formed in the condensation reaction. It is found in the GPC curve that the molecular weight of OTTP distribute within the scope from 700 to 4000, which indicates that the prepared OTTP is an oligomer. The weight-average molecular weight (Mw), number-average molecular weight (Mn), peak molecular weight (Mp), and z-average molecular weight (Mz) of OTTP are 919, 580, 812, and 1468 respectively. It is worth noting that the molecular weight distribution index (PDI\u0026thinsp;=\u0026thinsp;Mw/Mn) is 1.58. When the PDI is close to 1, it represents that the molecular weight shows a relatively narrow distribution characteristic, which means that the uniformity of the polymer molecule size is relatively high. In addition, the Mn value represents the number-weighted average of molecules with different molecular weights in the polymer, reflecting the overall size condition about the polymer molecules. The degree of polymerization is estimated by Mn/the molecular weight of the repeating unit. Polymerization degree of OTTP is 6.99, indicating that the prepared Schiff base polymer (OTTP) belongs to low molecular weight polymer. Figure \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eB is plotted with retention time as the abscissa and response as the ordinate. A narrow and sharp peak is observed in Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eB (in the 9.25\u0026ndash;9.75 retention min region), which indicates that OTTP is oligomer. This outcome agrees with the data of the GPC molecular weight distribution curve, and the molecular weight is centered within the range of 700 to 2000 (particularly in the 1000\u0026ndash;2000).\u003c/p\u003e\n \u003cp\u003eThe magnetic saturation value of samples is evaluated by VSM. The hysteresis loops of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 are measured in the magnetic field range of \u0026plusmn;\u0026thinsp;20K Oe, as illustrated in Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eC. The saturation magnetization of pure magnetic oxide particles is 65.3571 emu/g, and the saturation magnetization of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 is also around 65.3571 emu/g. This phenomenon occurs because considering the influence of economic cost and green chemistry, a small amount of Schiff base polymer to wrap Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e in the synthesis processes. The magnetic inorganic/organic hybrid material has good magnetism, which lays a certain foundation for the subsequent recycling of materials and reduces environmental pollution and waste of resources. Figure \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eD shows the infrared spectra of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2. Samples (Fe3O4, Fe3O4-OTTP-1 and Fe3O4-OTTP-2) have the characteristic peak at 1400 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 571 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, which corresponds to the Fe-O bond(Fu et al. \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e). The peak at 3432.9 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e corresponds to the -OH group. There is the characteristic peak at 1350.7 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, which is attributed to the symmetric deformation vibration of methyl. The characteristic peak corresponding to the C\u0026thinsp;=\u0026thinsp;N group can be seen at 1592.6 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e(Hamed et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Mingxiang Liu et al. \u003cspan class=\"CitationRef\"\u003e2023\u003c/span\u003e), indicating that the condensation reaction taking place and C\u0026thinsp;=\u0026thinsp;N bond forming in synthesis possesses.\u003c/p\u003e\n \u003cp\u003eThe XRD patterns of samples (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, OTTP, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) are shown in Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eE. There exist six diffraction peaks at 2\u0026theta;\u0026thinsp;=\u0026thinsp;30.2\u0026deg;, 35.5\u0026deg;, 43.2\u0026deg;, 53.7\u0026deg;, 57.4\u0026deg;, and 62.5\u0026deg;, which are attributed, respectively, to the (220), (311), (400), (422), (511), and (440) planes of the cubic type (b-Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e) phase(Koli et al. \u003cspan class=\"CitationRef\"\u003e2019\u003c/span\u003e; Mishra et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e). Schiff base organic polymer OTTP has the widen diffraction peak at 10\u0026deg;-15\u0026deg;, which demonstrates that OTTP polymer has better crystallization in comparison with traditional organic chemical compounds. The diffraction peaks of nano-Fe3O4 (30\u0026deg;-65\u0026deg;) and the characteristic diffraction peaks of OTTP (10\u0026deg;-15\u0026deg;) are observed together in samples (Fe3O4-OTTP-1 and Fe3O4-OTTP-2), it reveals that organic phase and inorganic phase co-exist through the synthesis reactions.\u003c/p\u003e\n \u003cp\u003eThe N\u003csub\u003e2\u003c/sub\u003e adsorption-desorption isotherms of samples (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) are shown in Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eF, and the BET data are listed in S1. The specific surface area of pure nano Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e is 38.6539 m\u003csup\u003e2\u003c/sup\u003e/g, while those of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 are 34.6209 m\u003csup\u003e2\u003c/sup\u003e/g and 25.8176 m\u003csup\u003e2\u003c/sup\u003e/g respectively. During the modification process of nano Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e by OTTP, OTTP molecules may block the pores on the particle surface, bringing about the decline of surface area. And the isotherm is type IV, indicating that the inorganic/organic hybrid materials have mesoporous microstructure(Walling et al. \u003cspan class=\"CitationRef\"\u003e2024\u003c/span\u003e). According to calculation, the pore diameter of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 is 17.1571 nm and the pore volume is 0.1519 cm\u003csup\u003e3\u003c/sup\u003e/g, and the pore diameter of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 is 23.0069 nm and the pore volume is 0.1233 cm\u003csup\u003e3\u003c/sup\u003e/g. The mesoporous structures of inorganic/organic hybrid materials (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) play important role for removing pollutants in wastewater. The pore size curves of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 are shown in Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003eG, and the relatively wide pores distribution is benefit for pollutants adsorption.\u003c/p\u003e\n \u003cp\u003eThe polycondensation reaction synthesis are confirmed by NMR analysis, o-tolidine, terephthalaldehyde and the schiff base polymer OTTP (using tetrahydrofuran-d8 as the solvent) are measured respectively. It can be seen that o-tolidine has an obvious chemical shift at 3.62 ppm, which is ascribe to -NH\u003csub\u003e3\u003c/sub\u003e (Fig. \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003eA). As shown in Fig. \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003eB, terephthalaldehyde shows obvious signal at 10.07 ppm, in accordance with the aldehyde unit (-CHO). It is worthy noting that the strength of the aldehyde group of OTTP shows weakening tendency. In addition, as shown in Fig. \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003eC, OTTP has a new chemical shift at 8.45 ppm, which is originated from the CH\u0026thinsp;=\u0026thinsp;N bond(MuĞLu et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e). In addition, some intricate shifts dispersed between 8.32\u0026ndash;6.80 ppm may result from hydrogen on the aromatic ring(Hye Kyong Kim et al. \u003cspan class=\"CitationRef\"\u003e2010\u003c/span\u003e). These NMR results can be compared together, and the conclusion is obtained clearly that Schiff base condensation reaction is the appropriate approach for polymer preparation.\u003c/p\u003e\n\u003c/div\u003e\n\u003ch3\u003eAdsorption performance of magnetic composite materials\u003c/h3\u003e\n\u003cp\u003eThe adsorption experiments of magnetic inorganic/organic hybrid materials (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) were investigated using rhodamine B as the pollutant (Fig. \u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003eA), and nano Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e particles was used as the blank reference sample. It can be seen that Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 have the best adsorption capability among all measured samples, and the removal rate of rhodamine B is up to 94.36%. The blank reference sample (nano Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e particles) possess the lowest adsorption capacity and the lowest removal rate of rhodamine B (Q\u003csub\u003ee\u003c/sub\u003e = 3.06, removal rate\u0026thinsp;=\u0026thinsp;6.80%). While nano Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e particles are encapsulated by Schiff base polymer, the magnetic cores are still maintained and the additional adsorption capability of rhodamine B are endowed by the organic polymers coating. Schiff base polymers coating could interact with rhodamine B through intermolecular forces, such as van der Waals force and \u0026pi;-\u0026pi; stacking, therefore, the adsorption capacity and the removal rate are increase. However, the adsorption capacity of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 is different from the sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2, a reasonable explain is that the quantity of organic coating layer is different, the mole ratio (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e : OTTP, where OTTP select the molecular weight of basic structural units, 310.4) demonstrates the comparison of relative content of inorganic composition/organic composition, the ratio of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 is 1.12, which is smaller than the ratio of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (5.6), indicating that the more organic molecular basic units are contented in the sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and the more active adsorption sites of rhodamine B are maintained in the sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1.\u003c/p\u003e\n\u003cdiv id=\"Sec11\" class=\"Section2\"\u003e\n \u003ch2\u003eAdsorption performance of rhodamine B with different conditions\u003c/h2\u003e\n \u003cp\u003eIn order to evaluate the applicable scope and feasibility of magnetic composites, important factors such as temperature, adsorbent dosage and PH value are taken into consideration. The adsorption capacity and removal rate are researched with different adsorption temperature (20\u0026ndash;40\u0026deg;C). It can be observed from Fig. \u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003eB that the best adsorption performance of all samples is 40\u0026deg;C (Q\u003csub\u003ee1\u003c/sub\u003e = 44.26, Remove rate\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;98.35%; Q\u003csub\u003ee2\u003c/sub\u003e = 18.26, Remove rate\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;40.58%). Because the molecule thermal movement velocity increase with the adsorption temperature increasing, the more molecules can reach the surface of the adsorption materials, access to the adsorption sites and undergo adsorption reactions. According to Fig. \u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003eC, the adsorption capacity of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 is the largest at 0.005g (Q\u003csub\u003ee1\u003c/sub\u003e = 139.08), while the adsorption capacity of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 is the largest at 0.035g (Q\u003csub\u003ee2\u003c/sub\u003e = 10.71). Sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 have the higher proportion of adsorption effective active sites at a lower dose (0.005g), which can contact and adsorb rhodamine B, thereby reaching the maximum adsorption capacity. Sample Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 require the higher adsorbent dosage (0.035g) to provide active sites and reach the maximum adsorption capacity. When selected the same adsorbent dosage 0.035g, both materials have enough active sites to absorb rhodamine B, resulting in the maximum removal rate.\u003c/p\u003e\n \u003cp\u003eThe effect of PH on rhodamine B adsorption is shown in Fig. \u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003eD, samples (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) possess the high removal rates under acidic conditions (Remove rate\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;100.00%; Remove rate\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;52.58%). In acidic condition, functional groups are easily protonated, making the surface of the adsorbent carry positive charges. Rhodamine B is a cationic coloring agent and also mainly exists in cationic form under acidic conditions. Due to electrostatic attraction, the interaction force between magnetic composite materials and rhodamine B molecules increases, thereby increasing the adsorption capacity.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec12\" class=\"Section2\"\u003e\n \u003ch2\u003eAdsorption kinetics of rhodamine B with samples\u003c/h2\u003e\n \u003cp\u003eIn the research, the pseudo-first-order kinetic model, pseudo-second-order kinetic model, Elovich model and Weber-Morris intraparticle diffusion model, and provided fitting diagrams and relevant fitting parameters (Fig. \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003eA, \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003eB, \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003eC, \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003eD and Table S2) were used to evaluate adsorption kinetics processes. It reveals that the optimal correlation exists between the pseudo-second-order equation and the obtained outcome, indicating that the adsorption models of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 for rhodamine B are more inclined to the pseudo-second-order kinetic model. Meanwhile, chemical adsorption takes the leading role (Jiang et al. \u003cspan class=\"CitationRef\"\u003e2019\u003c/span\u003e). As demonstrated in the Fig. \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003eA and \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003eC, the correlation between reaction time and adsorption capacity is presented. The adsorption amount keeps increasing as the reaction time lengthens, reaching a state of equilibrium when the reaction concludes. At the start of the experiment, the growth of removal ability is associated with plentiful adsorption vacant sites. But the saturation of these adsorption sites occurs progressively, resulting in the decline of the adsorption capacity(Wei et al. \u003cspan class=\"CitationRef\"\u003e2022a\u003c/span\u003e). The pseudo-second-order kinetic model is better with fitting data.\u003c/p\u003e\n \u003cp\u003eThe Elovich model postulates that the adsorbent active sites are non-uniform, and shows diverse activation energies for the adsorption of organics (Zhao et al. \u003cspan class=\"CitationRef\"\u003e2017\u003c/span\u003e). In addition, through the Elovich model parameter (1/a), the stability of the adsorption process can also be analyzed. The smaller 1/a is, the more stable the adsorption process is. Therefore, the adsorption stability of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (1/a\u0026thinsp;=\u0026thinsp;0.2886) is greater than that of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (1/a\u0026thinsp;=\u0026thinsp;12.5786). The Elovich model can reflect the rate change in the adsorption process. Generally speaking, as the adsorption proceeds, the adsorption rate may gradually decrease, which is associated with how saturated the adsorption sites are. The adsorption capacity obtained from the experiment is very approximate the theoretical value forecasted by the model. These discoveries indicate that the adsorption course fully follows the Elovich model. Through the analysis of the Weber-Morris intraparticle diffusion model, we can deeply understand the diffusion of adsorbates inside the adsorbent particles and provide an important foundation for study of the adsorption process mechanism and the design of adsorbents. Since the intraparticle diffusion model is capable of fitting the experimental data effectively and the intraparticle diffusion rate is relatively fast in the entire adsorption process, it implies that intraparticle diffusion may be limiting the rate of removal, that is, the diffusion of rhodamine B inside the particles of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 controls the adsorption rate(Zhiyuan Liu et al. \u003cspan class=\"CitationRef\"\u003e2024b\u003c/span\u003e).\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec13\" class=\"Section2\"\u003e\n \u003ch2\u003eAdsorption isotherm of rhodamine B with samples\u003c/h2\u003e\n \u003cp\u003eAdsorption isotherm is a curve that depicts the association between the adsorption amount of adsorbent to adsorbate and the equilibrium at a certain temperature. In this work, different isotherm models are used to understand the relevant fitting parameters (as depicted in the Fig. \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003eE-F and Table S3). The Langmuir adsorption isotherm successfully describes that adsorbed molecules and adsorption sites exhibit monolayer adsorption. In contrast to the Langmuir isotherm, the Freundlich isotherm is frequently utilized to depict multilayer adsorption taking place on non-uniform surface. Table S3 shows that the fitting coefficient of the Langmuir adsorption isotherm exceeds that of the Freundlich isotherm, indicating that the removal of rhodamine B occurs uniformly on the surface of magnetic materials and this kind of adsorption is single-layer adsorption.\u003c/p\u003e\n \u003cp\u003eThe effectiveness of the adsorption reaction is evaluated by the Langmuir adsorption model parameter R\u003csub\u003eL\u003c/sub\u003e (R\u003csub\u003eL\u003c/sub\u003e = 1/ (1\u0026thinsp;+\u0026thinsp;KC\u003csub\u003e0\u003c/sub\u003e)). When 0\u0026thinsp;\u0026lt;\u0026thinsp;R\u003csub\u003eL\u003c/sub\u003e \u0026lt; 1, it indicates that the process is advantageous (Shehzad et al. \u003cspan class=\"CitationRef\"\u003e2019\u003c/span\u003e). Through calculation, it is proved that the adsorption processes of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (R\u003csub\u003eL\u003c/sub\u003e = 0.1836) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (R\u003csub\u003eL\u003c/sub\u003e = 0.3658) are favorable. The parameter n of the Freundlich isotherm reflects the adsorption strength or the affinity between the adsorbent and the adsorbate. Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (n\u0026thinsp;=\u0026thinsp;0.6649) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (n\u0026thinsp;=\u0026thinsp;0.4390) have good adsorption-desorption capabilities, providing a underpinning for the recycling of materials(Aghaei et al. \u003cspan class=\"CitationRef\"\u003e2023\u003c/span\u003e). The Sips adsorption model is an adsorption model that combines the features of the Langmuir model and the Freundlich model. When n\u003csub\u003es\u003c/sub\u003e = 1, the Sips model degenerates into the Langmuir model, when n\u003csub\u003es\u003c/sub\u003e approaches 0, the Sips model is close to the Freundlich model(Zhen Wu et al. \u003cspan class=\"CitationRef\"\u003e2017b\u003c/span\u003e). And Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 (n\u003csub\u003es\u003c/sub\u003e = 0.6895) and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 (n\u003csub\u003es\u003c/sub\u003e = 0.6217) are both nearly 1, signifying that the adsorption process of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 for rhodamine B is ideal monolayer adsorption. An empirical adsorption model, the Toth adsorption model is used to describe the behavior of the adsorbents. The value of K\u003csub\u003eT\u003c/sub\u003e of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 is relatively small, which indicates that the compatibility of the adsorbent to the adsorbate is weak(Kumar et al. \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e), which is consistent with the results obtained from the Freundlich isotherm.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec14\" class=\"Section2\"\u003e\n \u003ch2\u003eThe XPS spectra of samples (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) adsorbed rhodamine B\u003c/h2\u003e\n \u003cp\u003eThe XPS spectra were performed to confirm rhodamine B adsorption state on surface of magnetic inorganic/organic hybrid materials, and the results are shown in Fig. \u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003eA-E. In the Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 sample, the content of C\u0026thinsp;=\u0026thinsp;C bond is 70.92% and the content of C\u0026thinsp;=\u0026thinsp;N bond is 29.08% respectively. After adsorbed rhodamine B in the Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 sample, the content of C\u0026thinsp;=\u0026thinsp;C bond is 90.15% and the content of C\u0026thinsp;=\u0026thinsp;N bond is 8.85%. And in the Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 sample, the content of C\u0026thinsp;=\u0026thinsp;C bond is 70.54% and the content of C\u0026thinsp;=\u0026thinsp;N bond is 29.46% respectively. After adsorbed rhodamine B in the Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 sample, the content of C\u0026thinsp;=\u0026thinsp;C bond is 72.32% and the content of C\u0026thinsp;=\u0026thinsp;N bond is 27.68%. These results demonstrate that the removal rhodamine B ability of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 is better than that of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2, which is consistent with the adsorption kinetics experimental results. It is precisely due to the \u0026pi;-electron interaction between Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 and rhodamine B, and the content of C-C/C\u0026thinsp;=\u0026thinsp;C becomes greater.\u003c/p\u003e\n \u003cp\u003eAfter rhodamine B were absorbed by samples (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2), FTIR and XRD characterizations were performed for confirming adsorption state (Fig. \u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003eF-G). There are several peaks at 3201 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, 1700 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 1487 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, which are attributed to the stretching vibrations of benzene rings and other aromatic ring structures in the molecular structure of rhodamine B, the extensional vibrations of -COOH, and the stretching oscillation of C-H bonds on benzene rings and hydrogen atoms on other unsaturated carbons. The XRD patterns are shown in Fig. \u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003e-R, it is not new phases discovering after adsorbed rhodamine B, which indicates that adsorption does not have an adverse effect on the magnetic composite material.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec15\" class=\"Section2\"\u003e\n \u003ch2\u003eRegeneration of samples (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2)\u003c/h2\u003e\n \u003cp\u003eIn general, absorbents can be regenerated by thermal regeneration method(Hak-Hyeon Kim et al. \u003cspan class=\"CitationRef\"\u003e2024\u003c/span\u003e), vacuum regeneration method(Yongbiao et al. \u003cspan class=\"CitationRef\"\u003e2024\u003c/span\u003e), chemical regeneration method(Moxi and Xue-yi \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e) and electrochemical regeneration method(Yasri and Roberts \u003cspan class=\"CitationRef\"\u003e2024\u003c/span\u003e). The thermal regeneration method possesses some advantages, such as simple operation, stable regeneration effect and environmental friendliness. In this experiment, the thermal regeneration temperature is selected 200\u0026deg;C and the regeneration holding-time is selected 3 hours. After the adsorption reaction is completed, the adsorbent is separated by an external magnet and then subjected to heat treatment for the regeneration experiment. The regeneration performance of samples (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) is shown in Fig. \u003cspan class=\"InternalRef\"\u003e8\u003c/span\u003e. After four adsorption-thermal regeneration cycles, the adsorption rate of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 is 26.80% and the adsorption rate of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 is 25.02%. It can be seen that the adsorption capability of materials (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) decrease with the adsorption-thermal regeneration cycles increasing, a possible explain is the microstructure destruction of inorganic/organic hybrid materials. Moreover, the surface functional groups of samples happen thermal decomposition or chemical reactions, lead to surface active adsorption sites decreasing. At the same time, some rhodamine B molecules still remain inside the magnetic schiff base composite material, and rhodamine B molecules of solution is difficult to adsorb on surface active sites of magnetic complicate materials.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec16\" class=\"Section2\"\u003e\n \u003ch2\u003eCalculation based on theory and mechanism\u003c/h2\u003e\n \u003cp\u003eIn order to understand the \u0026pi;-\u0026pi; interaction in rhodamine B molecules adsorption processes, theoretical calculations were performed during the implementation of this work. Here, density functional calculations (DFT) are mainly performed through several aspects such as structure optimization, monomer energy calculation, combination energy calculation, analytical visualization of molecular orbitals and electrostatic potential diagrams. The calculation of monomer energy and binding energy is carried out on the basis of structure optimization. Figure \u003cspan class=\"InternalRef\"\u003e9\u003c/span\u003eA-E are the structure optimization diagrams of OTTP and rhodamine B respectively. Among the molecular orbitals, the uppermost occupied molecular orbital (HOMO) and the lowermost unoccupied molecular orbital (LUMO) play important roles for molecular properties. In the analytical visualization of molecular orbitals, HOMO orbital and LUMO orbital are selected for analysis(Lin et al. \u003cspan class=\"CitationRef\"\u003e2024\u003c/span\u003e). Figure \u003cspan class=\"InternalRef\"\u003e9\u003c/span\u003eB-D are the HOMO orbital, the LUMO orbital and the electrostatic potential diagrams of Fe3O4-OTTP respectively. Figure \u003cspan class=\"InternalRef\"\u003e9\u003c/span\u003eF-H are the HUMO orbital, the LUMO orbital and the electrostatic potential diagrams of rhodamine B respectively.\u003c/p\u003e\n \u003cp\u003eIf there are differences in the LUMO and HOMO molecular orbital diagrams of two reactants, it is considered that there is an electron donor-acceptor interaction. Generally, Fe3O4-OTTP hybrids materials act as electron donor, and rhodamine B act as an electron acceptor. Furthermore, the steadiness of charge distribution during the adsorption process is studied through the characteristics of electrostatic potential distribution. The distribution of positive and negative electrostatic potential regions in the system are shown in Fig. \u003cspan class=\"InternalRef\"\u003e9\u003c/span\u003e-H. The blue regions represent that they are relatively electron-deficient and have a positive electrostatic potential, and the potential electron acceptor regions show stronger electrophilicity relative to other regions. Meanwhile, the negative electrostatic potential regions (red regions) indicate that they are relatively electron-rich and may be potential electron donor regions or are more nucleophilic than other regions(Mabkhot et al. \u003cspan class=\"CitationRef\"\u003e2017\u003c/span\u003e; Vijay et al. \u003cspan class=\"CitationRef\"\u003e2019\u003c/span\u003e). Calculation results show that the charge distribution of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP is close to neutral, and the electrostatic potential of rhodamine B is tendency to negative potential.\u003c/p\u003e\n \u003cp\u003eThe combination energy (\u0026Delta;E) of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP and rhodamine B molecules in the context of numerous stacking modes, calculations of the combination energy (\u0026Delta;E) can be made by means of the following formula:\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec17\" class=\"Section2\"\u003e\n \u003cp\u003e\u0026Delta;E\u0026thinsp;=\u0026thinsp;E\u003csub\u003e(Fe3O4\u0026minus;OTTP\u0026middot;\u0026middot;\u0026middot;rhodamine B)\u003c/sub\u003e \u0026ndash; E\u003csub\u003e(Fe3O4\u0026minus;OTTP)\u003c/sub\u003e \u0026ndash; E\u003csub\u003e(rhodamine B)\u003c/sub\u003e\u003c/p\u003e\n \u003cp\u003ewher\u003cem\u003ee E\u003c/em\u003e\u003csub\u003e\u003cem\u003e(Fe3O4\u0026minus;OTTP\u0026middot;\u0026middot;\u0026middot;rhodamine B)\u003c/em\u003e\u003c/sub\u003e, \u003cem\u003eE\u003c/em\u003e\u003csub\u003e\u003cem\u003e(Fe3O4\u0026minus;OTTP)\u003c/em\u003e\u003c/sub\u003e \u003cem\u003eand E\u003c/em\u003e\u003csub\u003e\u003cem\u003e(rhodamine B)\u003c/em\u003e\u003c/sub\u003e correspond to the energies of the optimized Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP\u0026middot;\u0026middot;\u0026middot;rhodamine B, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP and rhodamine B structures respectively.\u003c/p\u003e\n \u003cp\u003eDue to the large size of rhodamine B molecules, errors may occur during calculation. Therefore, five stacking methods with smaller errors are proposed to calculate their binding energy. During the process of setting the stacking mode, the distance between the aromatic rings in Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP and rhodamine B molecules is set to 3 \u0026Aring;. First, these five stacking modes are optimized. The optimized structures are shown in Fig. \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eA-Q, and the distances between C-C in the aromatic rings are shown in Table S4. The binding energies corresponding to the five stacking modes are listed in Table S5. The total energies of the five magnetic materials and rhodamine B are ranked as V (-2915.817720 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;III (-2915.816619 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;IV (-2915.807424 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;II (-2915.802948 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;I (-2915.790560 a.u), and the arrangement order of \u0026Delta;E (a.u) values is also V (-0.044045 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;III (-0.042944 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;IV (-0.033749 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;II (-0.029273 a.u)\u0026thinsp;\u0026lt;\u0026thinsp;I (-0.016885 a.u). These calculation results indicate that the best bonding mode simulated during the adsorption process is type I.\u003c/p\u003e\n \u003cp\u003eIt can be found that the HOMO and LUMO orbits of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP change (as shown in Fig. \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eB, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eC, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eF, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eG, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eJ, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eK, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eN, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eO, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eR, and \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eS) in the rhodamine B adsorption processes, indicating that rhodamine B has been adsorbed on the magnetic inorganic/organic hybrid materials. In addition, after rhodamine B adsorption, the E\u003csub\u003eGAP\u003c/sub\u003e (E\u003csub\u003eGAP\u003c/sub\u003e = E\u003csub\u003eLUMO\u003c/sub\u003e - E\u003csub\u003eHOMO\u003c/sub\u003e) value also changes, indicating that the electron donor-acceptor interaction between molecules may be affected during the adsorption process, thereby affecting the stability of adsorption. Figure \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eD, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eH, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eL, \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eP, and \u003cspan class=\"InternalRef\"\u003e10\u003c/span\u003eT are electrostatic potential diagrams under five different stacking modes. It can be seen that after adsorption, the five stacking modes show cationic characteristics and negative potential distribution.\u003c/p\u003e\n \u003cp\u003eIn light of experimental and theoretical analysis, the main principle about the adsorption process is summarized in Fig. S3. In the start of adsorption, rhodamine B molecules reach the outer surface of the magnetic Schiff base composite material through membrane diffusion, and then reach the inner surface of the magnetic schiff base composite material through internal diffusion. Subsequently, rhodamine B molecules are effectively adhered to Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1 and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2 through chemical interactions, such as the \u0026pi;-\u0026pi; stacking interaction, the interaction between electron donor and acceptor. Finally, the adsorption processes reach the equilibrium state because the active sites have been absorbed rhodamine B molecules. Simultaneously, the additional interaction between rhodamine B molecules and magnetic composite materials come from other forces including van der Waals force, hydrophobic interaction and electrostatic attraction(Youwen et al. \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e).\u003c/p\u003e\n\u003c/div\u003e"},{"header":"Conclusions","content":"\u003cp\u003eIn this paper, magnetic inorganic/organic hybrid materials (Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) were prepared by situ polymerization method from o-Tolidine and p-phthalaldehyde. Schiff base polymer shells provide numerous active sites for rhodamine B adsorption, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e magnetic cores of the inorganic/organic hybrid materials separated the adsorbed rhodamine B from wastewater easily. The following conclusions can be drawn.\u003c/p\u003e\u003cp\u003e(1) Magnetic inorganic/organic hybrid materials (Fe3O4-OTTP-1, Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP-2) possess excellent rhodamine B adsorption capability, these magnetic core-shell hybrid materials have potential application in organic dyes removing.\u003c/p\u003e\u003cp\u003e(2) According to adsorption isotherm research, rhodamine B adsorption on magnetic inorganic/organic hybrid materials are consistent with the Langmuir adsorption model, indicating that homogeneous monolayer is formed in the adsorption processes.\u003c/p\u003e\u003cp\u003e(3) According to theoretical calculations, the charge distribution of Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e-OTTP is close to neutral, and the electrostatic potential of rhodamine B is tendency to negative potential. And in rhodamine B adsorption, the E\u003csub\u003eGAP\u003c/sub\u003e (E\u003csub\u003eGAP\u003c/sub\u003e = E\u003csub\u003eLUMO\u003c/sub\u003e - E\u003csub\u003eHOMO\u003c/sub\u003e) value also changes, indicating that the electron donor-acceptor interaction can be affected during the adsorption process.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAcknowledgements\u003c/strong\u003e\u003cstrong\u003e：\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThis work was supported by the National Natural Science Foundation of China (51678059，42407081), the Fundamental Research Funds for the Central Universities, CHD (300203211293), the Innovative Research Team for Science and Technology of Shaanxi Province (2022TD-04), the Postdoctoral Fellowship Program of CPSF under Grant Number (GZC20232222).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthor contributions\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eLiuqing Li: Experimental design, carrying out measurements and manuscript write. Zhengwen Wei: Conception, manuscript revision. Zhenyi Jiang: Theoretical calculations. Xiangfei Lv: Characterization data analysis. Wei Wang: Conception, experimental design.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflicts of interest or competing interests\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData and code availability\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAll data included in this study are available upon request by contact with the corresponding author.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eSupplementary information\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAny additional material omitted from the manuscript are described in the supplementary material section.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eEthical approval\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThere are no ethical issues involved in this study.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n \u003cli\u003eAghaei F., Tangestaninejad S., Bahadori M., Moghadam M., Mirkhani V., Mohammadpoor Baltork I., Khalaji M., Asadi V. 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Journal of Hazardous Materials, 403:123810. https://doi.org/10.1016/j.jhazmat.2020.123810\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":true,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"chemical-papers","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"chpa","sideBox":"Learn more about [Chemical Papers](http://link.springer.com/journal/11696)","snPcode":"11696","submissionUrl":"https://www.editorialmanager.com/CHPA/default.aspx","title":"Chemical Papers","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Absorption, Chemical synthesis, Core/shell, Magnetic properties, Polymer, X-ray photoelectron spectroscopy (XPS)","lastPublishedDoi":"10.21203/rs.3.rs-6728589/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-6728589/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eMagnetic inorganic/organic hybrid materials were prepared by situ polymerization method from o-Tolidine and p-phthalaldehyde. The study employed various techniques to characterize morphology and phase composition. Rhodamine B was select as the indicator pollutants to investigate the adsorption capability of magnetic inorganic/organic hybrid materials, The magnetic schiff base composite materials have excellent adsorption capacity. The density functional theory calculation (DFT) is employed to understand the structural optimization and adsorption energy in different adsorption configuration modes. During the adsorption process, rhodamine B molecules are mainly dominated by the π-π force, accompanied by van der Waals force, hydrophobic interaction, electrostatic attraction and electron donor-acceptor interaction. Schiff base polymer shells provide numerous active sites for rhodamine B adsorption, and Fe\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e magnetic cores of the inorganic/organic hybrid materials separated the adsorbed rhodamine B from wastewater easily. This kind of magnetic inorganic/organic hybrid materials have potential application in organic dyes removing.\u003c/p\u003e","manuscriptTitle":"Preparation of magnetic Schiff base nanocomposites for removal of Rhodamine B","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-07-14 15:25:59","doi":"10.21203/rs.3.rs-6728589/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"reviewerAgreed","content":"","date":"2025-07-09T15:51:44+00:00","index":0,"fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-07-09T15:50:39+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"Chemical Papers","date":"2025-06-30T19:38:05+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-05-26T11:05:15+00:00","index":"","fulltext":""},{"type":"submitted","content":"Chemical Papers","date":"2025-05-23T11:24:59+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"chemical-papers","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"chpa","sideBox":"Learn more about [Chemical Papers](http://link.springer.com/journal/11696)","snPcode":"11696","submissionUrl":"https://www.editorialmanager.com/CHPA/default.aspx","title":"Chemical Papers","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"3a43fd9b-005d-408f-ab70-96f445b9e3a8","owner":[],"postedDate":"July 14th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-11-03T16:10:34+00:00","versionOfRecord":{"articleIdentity":"rs-6728589","link":"https://doi.org/10.1007/s11696-025-04436-3","journal":{"identity":"chemical-papers","isVorOnly":false,"title":"Chemical Papers"},"publishedOn":"2025-10-29 15:58:29","publishedOnDateReadable":"October 29th, 2025"},"versionCreatedAt":"2025-07-14 15:25:59","video":"","vorDoi":"10.1007/s11696-025-04436-3","vorDoiUrl":"https://doi.org/10.1007/s11696-025-04436-3","workflowStages":[]},"version":"v1","identity":"rs-6728589","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-6728589","identity":"rs-6728589","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}