Theoretical Studies and Photovoltaic Performance of 1,10- Phenanthroline Derivative Compound as a Multiple Anchor Group

Theoretical Studies and Photovoltaic Performance of 1,10- Phenanthroline Derivative Compound as a Multiple Anchor Group | 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 Theoretical Studies and Photovoltaic Performance of 1,10- Phenanthroline Derivative Compound as a Multiple Anchor Group Buse Ozsan, Seyda Aydoğdu, Arzu Hatipoğlu, Ibrahim Erden This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-8128370/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 18 Mar, 2026 Read the published version in Chemical Papers → Version 1 posted 10 You are reading this latest preprint version Abstract In this study, organic dyes (B1 and B3) with a D–π–A architecture were synthesized for use in dye-sensitized solar cells (DSSCs). The molecules were designed with triphenylamine as the electron donor, an imidazole bridge, and 1,10-phenanthroline as an anchoring unit to facilitate efficient electron transfer to the semiconductor (TiO₂) surface. The multi-anchor structure of B3 was intended to enhance power conversion efficiency (PCE) by enabling more efficient electron injection from the donor group to the semiconductor. Structural characterization of the dyes was performed using FT-IR, NMR, mass spectrometry, UV-Vis spectroscopy, and electrochemical measurements. Theoretical calculations were performed using the density functional theory (DFT) method with the 6-31G(d)/LANL2DZ basis set. Theoretical analysis revealed that lower band gap energy would facilitate electron transfer between the HOMO and LUMO levels, thus potentially increasing PCE values. The B3 compound exhibited a lower band gap energy compared to B1. The DSSC device incorporating the multi-anchor B3 dye achieved higher power conversion efficiency than the device containing the single-anchor B1 dye. Photovoltaic measurements showed that the DSSC device incorporating B3 achieved a PCE of 0.61%, whereas the device with B1 reached a PCE of 0.28%. The obtained results showed that B3 compound possesses promising structural properties for photovoltaic applications. 1 10-phenanthroline dye sensitized solar cell photovoltaic applications organic dyes Figures Figure 1 Figure 2 Figure 3 1. INTRODUCTION Recently, with the development of science and technology, the design and development of new materials has become more important. The developed materials should be processed in smaller sizes in order to work with high energy efficiency, show high performance, be economical and environmentally friendly and to give good results. Thin film materials have begun to be given priority in technology in order to develop more useful and effective products with less material. In this context, dye-sensitized solar cells (DSSCs), one of the thin-film-based photovoltaic technologies, have attracted particular attention. Dye-sensitized solar cells (DSSCs), first introduced in 1991 by O’Regan and Grätzel [ 1 ], are cost-effective and environmentally friendly alternatives to conventional silicon-based photovoltaics. These devices use a mesoporous semiconductor structure to convert sunlight directly into electricity. The mesoporous TiO₂ nanoparticle film, deposited on a transparent conductive substrate, functions as the photoanode and requires an adsorbed organic dye to act as the sensitizer. Charge transfer is enabled by an electrolyte containing a redox mediator-typically the I⁻/I₃⁻ couple-while the circuit is completed by a counter electrode, commonly platinum-coated conductive glass due to its high catalytic activity and stability. The electrolyte solution spreads between the two electrodes and fills the porous structure of the semiconductor, providing electrical contact between them [ 2 ]. Important properties are required to make the dye available for TiO 2 -based DSSCs. First, the dye needs to be absorbed primarily in the visible range and the near-infrared region. Secondly, it’s lowest unoccupied molecular orbital (LUMO) should be above the conduction band of TiO 2 for the electron injection, and its highest occupied molecular orbital (HOMO) should be lower than the redox potential of the electrolyte for the dye’s regeneration [ 3 ]. Organic photovoltaic devices, which convert solar energy into electrical energy, have garnered significant interest as part of next-generation solar cell research. Among these technologies, dye-sensitized solar cells (DSSCs) achieve this conversion through sensitizer molecules, some of which are designed using 1,10-phenanthroline derivatives. 1,10-Phenanthroline is used as an anchor group in the sensitizer structure to provide electron transfer in dye-sensitized solar cell (DSSCs). Typically, 1,10-phenanthroline coordinates to a metal center to form metal complexes that act as light-absorbing sensitizers. These complexes absorb sunlight and, through metal-to-ligand charge-transfer (MLCT) excitation, inject electrons into the conduction band of TiO₂. Derivatives of 1,10-phenanthroline can be structurally tuned to improve the stability and overall efficiency of this electron-transfer process [ 4 ]. Particularly, when used with ruthenium-based complexes, 1,10-phenanthroline derivatives can contribute to achieving highly efficient DSSCs. Although ruthenium (II)-based sensitizers demonstrate high power conversion efficiency, they have several disadvantages, such as being a rare metal, complex synthesis, and purification steps, being toxic and having a high cost. To overcome these drawbacks, metal-free organic sensitizers have been developed and applied in DSSC applications as alternatives to ruthenium (II)-based sensitizers [ 5 ]. The main function of the sensitizer in the DSSC structure is to absorb light and provide electrons to the semiconductor layer TiO 2 . To perform this function effectively, the sensitizer dye must be chemically bonded to the semiconductor surface. In D–π–A type sensitizer molecules, anchor groups play a crucial role because they determine both the charge-injection efficiency and the binding strength between the dye and the semiconductor surface [ 6 ]. In general, carboxylic acid is the most commonly used anchor group, it has good charge injection efficiency and good electron pairing between dyes and semiconductors, but under continuous illumination or the presence of water molecules, carboxyl groups are easily detached from the semiconductor surfaces, which will greatly reduce the dye loading amount and damage the overall performance of the devices [ 7 ]. To overcome this limitation, many researchers have investigated alternative anchor groups that offer improved stability on TiO₂ surfaces. In the literature review, it was found that there were two studies using 1,10-phenanthroline as an anchor group. The first study, employed 1,10-phenanthroline as an anchor group was conducted by Li-Peng Zhang et al. in 2015. They synthesized two new donor-acceptor organic dyes using 1,10-phenanthroline as a linker group. Both dyes were efficiently adsorbed onto the TiO 2 surface via the 1,10-phenanthroline anchor, making them suitable for dye-sensitized solar cells. The resulting DSSCs demonstrated maximum power conversion efficiency (PCE) of 4.04%. This study highlighted that 1,10-phenanthroline is a promising building block for organic dyes that do not contain carboxylic acid, serving as both an acceptor and an anchoring group [ 8 ]. Another study that two new metal-free organic dyes named S1 and S2 of the 2D-π-2A type were prepared by Hai-Lang Jia et al. in 2019, which were then used as sensitizers in DSSCs. Phenothiazine and carbazole groups were used as electron donors, and 1,10-phenanthroline anchoring groups were added to the acceptors to form the 2D-π-2A type structure. The results showed that both dyes could bind to the Lewis acid sites on the TiO 2 surface through the 1,10-phenanthroline anchoring group. The bidentate configuration helped improve electron injection efficiency and enhance dye adsorption stability. The DSSC based on S1 exhibited a PCE of 4.39%, an open-circuit voltage (V oc ) of 708 mV, a short-circuit current density (J sc ) of 9.39 mAcm⁻², and a fill factor (FF) of 65.99% under AM 1.5G irradiation [ 9 ]. These findings indicate that DSSC performance can be further improved through the development of more efficient anchoring groups. In this study, a metal-free sensitizer molecule design was made for use in DSSC applications. In the molecules designed as shown in Scheme 1 and 2 , it was aimed to increase the PCE value of the solar cell by presenting the electrons coming from a single direction through the donor group to the semiconductor surface through a structure containing 1,10-phenanthroline as a multiple anchor group. The Compounds B1 and B3, which have D-π-A and D-π-3A properties, were designed to be used as sensitizers in DSSC devices. Quantum chemical theoretical calculations were performed for B1 and B3 molecules using the Density Functional Theory (DFT) method in the Gaussian 09 program package. As a result of quantum chemical calculations, the electronic properties of B1 and B3 compounds designed as sensitizers in DSSCs were investigated and analyzed. Structural characterization of the sensitizers was performed by taking FTIR, ¹H-NMR, Q-TOF and UV-Vis spectroscopy. The photovoltaic performance of the fabricated solar cells was measured under the Solar Simulator. High PCE values of the DSSC devices were achieved by Current-Voltage (I-V) measurement. 2. EXPERIMENTAL 2.1. Materials and characterization All chemicals and solvents used in this study were of analytical grade and sourced from commercial suppliers. The FTIR spectra were obtained using a Spectrum One Perkin Elmer 1600 FTIR spectrophotometer. 1 H NMR spectra were recorded on a Varian UNITY INOVA 500MHz NMR spectrometer with CDCl 3 and MeOH as the solvent. Absorption spectra were measured using a Shimadzu-2600 UV-Vis spectrophotometer. MALDI-TOF mass spectra were measured on Bruker Microflex LT instrument. 2.2. Computational method In this study the geometry optimizations of compounds are conducted by using Density Functional Theory B3LYP functional with 6-31g(d,p) level in Gaussian 09 programme [ 10 ]. The frequency calculations are done after optimization calculations in order to verify the true geometries as global minimum with positive frequencies. Time Dependent Density Functional Theory (TD-DFT) calculations are done with CAM-B3LYP/6-31g(d,p) level for comparison purpose with the experimental ones. In order to obtain 1 H NMR of compounds Gauge Independent Atomic Orbital approach is used. The solvent effect of ethanol is considered by using Conductor Like Polarizable Continuum Model (CPCM) with the same level of theory [ 11 ]. The electronic nature of the compounds are discussed with Molecular Electrostatic Potential (MEP) surface and Frontier Molecular Orbitals (FMO). All the visualizations of compounds are done with GaussView 05 package programme [ 12 ]. The reactivity properties of the compounds are discussed using global reactivity descriptors. The dye-sensitized solar cell performance of the compounds is investigated using quantum chemical theoretical calculations (See Supplementary information). 2.3. Device preparation The preparation of the DSSC devices was carried out as follows: Fluorine-doped tin oxide (FTO) substrates were purchased from Spi Co. Ltd. The substrates were cleaned in an ultrasonic bath using a solution of acetone and isopropanol, and then rinsed with distilled water for 10 minutes. They were dried with nitrogen gas to ensure optimal mechanical contact between the conductive FTO surface and titanium dioxide (TiO 2 ), as well as to protect the FTO surface from interaction with the electrolyte. The photoanodes consisting of a 15–20 µm thick TiO₂ layer were prepared following the procedure described in the literature [ 13 ]. The TiO₂ paste was coated onto the cleaned FTO substrates using the doctor blade technique, wherein a metal strip was used to evenly spread the paste. The coated TiO₂ layer was subsequently heated to 400°C in air and sintered at this temperature for 3 hours. After sintering step, the TiO 2 film was stained by immersing into 1x10 − 4 M dye solution containing B1 and B3 at room temperature for 24 h, respectively. Finally, a platinized FTO counter electrode was manually pressed onto the assembled device. The platinized FTO substrate was prepared by immersing it in an H₂PtCl₄ solution and subsequently heating it at 450°C for 10 minutes. After drying under an air stream, the sensitized TiO₂ electrode was sandwiched with a thermally platinized counter electrode separated and sealed. The electrolyte solution, composed of 0.5 M potassium iodide and 0.05 M iodine dissolved in pure ethylene glycol, was prepared following the procedure outlined by Smestad [ 14 ]. The electrolyte was injected into the gap between the electrodes by capillarity. The active area of the devices, determined by the overlapping regions of the anode and cathode, was set to 1 cm². The photovoltaic performance was determined under simulated sunlight. The current density versus voltage (J-V) characteristics of the cells were measured both in the dark and under simulated ABET 1.5 G solar illumination by using a Keithley 2400 Digital Source Meter at room temperature. 2.4. Synthesis 5-Nitro-1,10-phenanthroline [ 15 ], 5-Nitro-6-amino-1,10-phenanthroline [ 16 ], 5,6-Diamino-1,10-phenanthroline [ 16 ] and Tris(4-bromo phenyl) amine [ 17 ] were synthesized according to the literature procedures. 2.4.1. Synthesis of 4'-[bis(4-bromophenyl)amino]-[1,1'-biphenyl]-4-carbaldehyde (A1-Br 2 ) Tris(4-bromophenyl) amine (96.0 mg, 0.20 mmol), 4-formylphenylboronic acid (30.0 mg, 0.20 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.9 mg, 0.0033 mmol) were stirred at room temperature in 1,4-dioxane (20.0 mL) under an argon atmosphere. A 1.0 M aqueous Na₂CO₃ solution (5 mL) was added dropwise to the reaction mixture. The reaction mixture was heated to reflux at 100°C and stirred for 24 hours. After cooling to room temperature, the reaction mixture was extracted with CHCl₃ (3 × 10 mL). The organic phase was washed with water (5.0 mL), 1 M HCl (5.0 mL), and brine (5.0 mL), dried over anhydrous MgSO₄, filtered, and evaporated under vacuum. The crude product was obtained as a yellow powder (C 25 H 17 Br 2 NO: 507.217 g/mol)(Scheme SI.1). FTIR (ATR, cm⁻¹): 3061 cm⁻¹ (Ar), 1682 cm⁻¹ (C = O), 1484 cm⁻¹ (C = C). ¹H-NMR (500 MHz, CDCl 3 , ppm) δ 10.02 (s, 1H), 7.93 (d, 2H), 7.86 (d, 2H), 7.74 (d, 2H), 7.65 (d, 4H), 7.32 (d, 2H), 6.93 (d, 4H) (SI.13). 2.4.2. Synthesis of 4’-[bis({[1,1’-biphenyl]-4-yl})amino]-[1,1’-biphenyl]-4-carbaldehyde (A1) A1-Br 2 (101.4 mg, 0.20 mmol), phenylboronic acid pinacol ester (40.0 mg, 0.20 mmol), and tetrakis(triphenylphosphine)palladium(0) (7.7 mg, 0.0066 mmol) were stirred at room temperature in 1,4-dioxane (50.0 mL) under an argon atmosphere. A 1.0 M aqueous solution of Na₂CO₃ (5.0 mL) was added dropwise to the mixture. The mixture was heated to reflux at 100°C and stirred for 48 hours. The reaction mixture was cooled to room temperature and extracted with CHCl₃ (3 × 10 mL). The organic phase was washed with water (5.0 mL), 1 M HCl (5.0 mL), and brine (5.0 mL), dried over anhydrous MgSO₄, filtered, and evaporated under vacuum. The crude product was obtained as a yellow powder (C 37 H 27 NO: 501.62 g/mol). FTIR (ATR, cm⁻¹): 3058 cm⁻¹ (Ar), 1692 cm⁻¹ (C = O), 1483 cm⁻¹ (C = C) (Figure SI.9). UV-Vis (max., nm.): 220, 355. (Figure SI.5). ¹H-NMR (500 MHz, CDCl 3 , ppm) δ 10.12 (s, 1H), 8.03 (d, 2H), 7.95 (d, 2H), 7.83 (d, 6H), 7.75 (d, 6H), 7.54 (d, 4H), 7.17 (t, 4H), 7.10 (t, 2H) (Figure SI.14). 2.4.3. Synthesis of 4’-[bis({4’-formyl-[1,1’-biphenyl]-4-yl})amino]-[1,1’-biphenyl]-4-carbaldehyde (A3) Tris(4-bromo phenyl) amine (32.0 mg, 0.0667 mmol), 4-formylphenylboronic acid (30.0 mg, 0.20 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.9 mg, 0.0033 mmol) were stirred at room temperature in 1,4-dioxane (20.0 mL) under an argon atmosphere. A 1.0 M aqueous solution of Na₂CO₃ (5.0 mL) was added dropwise to the mixture. The mixture was heated to reflux at 100°C and stirred for 48 hours. The reaction mixture was cooled to room temperature and extracted with CHCl₃ (10.0 mL). The organic phase was washed with water (5.0 mL), 1 M HCl (5.0 mL), and brine (5.0 mL), dried over anhydrous MgSO₄, filtered, and evaporated under vacuum. The crude product was obtained as a yellow powder (C 39 H 27 NO 3 : 557.64 g/mol). Melting point: 230°C, Yield: 17 mg (54%). FTIR (ATR, cm⁻¹): 3069 cm⁻¹ (Ar), 1695 cm⁻¹ (C = O), 1485 cm⁻¹ (C = C) (Figure SI.10). UV-Vis (max., nm.): 220, 270, 385. (Figure SI.6). ¹H-NMR (500 MHz, CDCl 3 , ppm) δ 10.02 (s, 3H), 7.93 (d, 6H), 7.74 (d, 6H), 7.32 (d, 6H), 6.93 (d, 6H) (SI.15). Q-TOF ESI MS m/z [M+]: 557.18 g/mol, (Figure SI.18) [ 18 ]. 2.4.4. Synthesis of N,N-bis({[1,1’-biphenyl]-4-yl})-4’-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}-[1,1’-biphenyl]-4-amine (B1) 5,6-Diamino-1,10-phenanthroline (30.0 mg, 0.142 mmol) was dissolved in 20.0 mL of anhydrous ethanol, and the A1 compound (71.2 mg, 0.0473 mmol) dissolved in 30.0 mL of anhydrous ethanol, was added dropwise. The reaction mixture was stirred under reflux in argon atmosphere for 12 hours. The solvent was evaporated to one-third of its initial volume using a rotary evaporator, and then petroleum ether was added at room temperature. When the solution cooled to room temperature, a yellow precipitate was obtained. The precipitate was filtered and then recrystallized from a 2:1 n-hexane/ethyl acetate mixture. (C 49 H 33 N 5 : 691.82 g/mol). FTIR (ATR, cm⁻¹): 3285 cm − 1 (N-H), 3070 cm − 1 (aromatic C-H), 1577 cm − 1 (C = N), 1484 cm − 1 (C = C) (Figure SI.11). 1 H-NMR (500 MHz, CDCl 3 , ppm) δ 9.58 (d, 2H), 9.26 (d, 2H), 8.95 (s,1H), 8.18 (d, 2H), 7.77 (d, 2H), 7.57 (d, 4H), 7.29 (d, 6H), 7.02 (m, 2H), 6.96 (m, 4H), 6.91 (m, 2H), 6.85 (d, 6H) (SI.16). MALDI-TOF [M + 1] + 5H 697.84 g/mol (Figure SI.19). 2.4.5. Synthesis of 4’-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}-N,N-bis(4’-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}-[1,1’-biphenyl]-4-yl)-[1,1’-biphenyl]-4-amine(B3) 5,6-Diamino-1,10-phenanthroline (30.0 mg, 0.142 mmol) was dissolved in 30.0 mL of anhydrous ethanol, and the A3 compound (26.4 mg, 0.0473 mmol) dissolved in 10.0 mL of anhydrous ethanol, was added dropwise. The reaction mixture was stirred under reflux in argon atmosphere for 12 hours. The solvent was evaporated to one-third of its initial volume using a rotary evaporator, and petroleum ether was added at room temperature. When the solution cooled to room temperature, a yellow precipitate was obtained. The precipitate was filtered and then recrystallized from a 2:1 n-hexane/ethyl acetate mixture. (C 75 H 45 N 13 : 1128 g/mol). Melting point: 340°C, Yield: 27 mg (52%). FTIR (ATR, cm⁻¹): 3290 cm⁻¹ (N-H), 3080 cm⁻¹ (Aromatic), 1595 cm⁻¹ (C = N), 1470 cm⁻¹ (C = C) (Figure SI.12). ¹H-NMR (500 MHz, MeOH, ppm): δ 9.67 (s, 3H), 8.88 (d, 3H), 8.83 (d, 3H), 8.30 (dd, 6H), 7.69 (d, 6H), 7.55 (d, 6H), 7.45 (td, 6H), 6.92 (d, 6H), 6.83 (d, 6H) (SI.17). MALDI-TOF [M + 1]Na⁺ 1151 g/mol (Figure SI.20). 3. Results and Discussion 3.1. Characterization As seen in Schemes 1 and 2 , compounds B1 and B3 were synthesized purely and in good yields. In the synthetic procedure, the tris(4-bromophenyl)amine, obtained by the bromination of triphenylamine, was first reacted with 4-formylphenylboronic acid in appropriate molar ratios to afford the intermediates A1 and A3, as shown in Schemes SI.1 and SI.2 in the Supplementary Information. Subsequently, compounds A1 and A3 were separately reacted with 5,6-diamino-1,10-phenanthroline to afford compounds B1 and B3, respectively, as shown in Schemes SI.3 and SI.4. The resulting compounds were purified using a variety of methods and characterized in their pure form by FTIR, UV-Vis, 1 H-NMR, and MALDI-MS spectroscopy. In the UV-Vis spectrum analysis of the synthesized compounds B1 and B3, π-π* transitions were observed in the range of 250–350 nm, while n-π* transitions appeared between 350–400 nm, as shown in Figures SI.7 and SI.8. The calculated TD-DFT results are given in Table 1 . As seen in Table 1 , the main transition of compound B1 occurs from HOMO to LUMO with a contribution of 53.79%. The maximum wavelength of this transition is 336.26 nm and this result is in good agreement with the experimental one, the percentage error is 0.51%. For compound B3, the main transition occurs from HOMO to LUMO with a contribution of 55.90%. The maximum wavelength of this transition is 342.74 nm, and this result is in good agreement with the experimental data, with a percentage error of 3.18%. Another important transition occurs between HOMO-1 and LUMO. Spectral calculation results for orbital contributions are given in Figures SI.3 and SI.4. When the FTIR spectra of compounds B1 (Figures SI.11) and B3 (Figures SI.12) were evaluated, characteristic vibration bands belonging to the -NH group in the imidazole ring were observed at 3285–3290 cm − 1 and 3526–3527 cm − 1 for the experimental and calculated, respectively. In addition, the vibration bands belonging to the C = O group seen at 1692 cm − 1 and 1695 cm − 1 in the structure of compounds A1 (Figures SI.9) and A3 (Figures SI.10) and the vibration bands belonging to the -NH 2 group seen at 3370 and 3267 cm − 1 in the structure of 5,6-diamino-1,10-phenanthroline are not seen in the FTIR spectrum of molecules B1 and B3. This supports the formation of the imidazole ring in the structure of compounds B1 and B3. The comparison of calculated and experimental frequencies is given in Table SI.1. As seen in Table SI.1, the frequencies are compatible with each other. Table 1 Calculated wavelengths (nm), excitation energies (eV), oscillator strength, and orbital contributions for compound B1 and B3. Λ (nm) E ex (eV) f Orbital Contribution λexp (nm) B1 336.26 3.69 2.12 HOMO \(\:\to\:\) LUMO (53.79%) 338 HOMO-1 \(\:\to\:\) LUMO (17.50%) HOMO-1 \(\:\to\:\) LUMO + 4 (2.62%) HOMO → LUMO + 1 (4.87%) HOMO → LUMO + 2 (7.67%) HOMO + 1 → LUMO + 4 (4.50%) B3 342.74 3.62 2.64 HOMO \(\:\to\:\) LUMO (55.90%) 354 HOMO-3 \(\:\to\:\) LUMO + 1 (2.04%) HOMO-2 \(\:\to\:\) LUMO + 1 (5.58%) HOMO-1 → LUMO + 2 (7.95%) HOMO → LUMO + 3 (2.47%) HOMO → LUMO + 6 (3.74%) HOMO → LUMO + 11 (4.14%) The aldehyde proton of A1 (10.12 ppm) and the –NH₂ protons of 5,6-diamino-1,10-phenanthroline (4.4 ppm) disappeared in the ¹H-NMR spectrum of B1. It was observed that a singlet -NH proton belonging to the imidazole ring was formed at 8.95 ppm in the structure. The aldehyde proton of A3 (10.02 ppm) and the –NH₂ protons of 5,6-diamino-1,10-phenanthroline (4.4 ppm) disappeared in the ¹H-NMR spectrum of B3. It was observed that a singlet -NH proton belonging to the imidazole ring was formed at 9.67 ppm in the structure. Also, the calculated 1 H-NMR results are in good agreement with the experimental results (Table SI.2). In the Q-toff spectrum, the molecular ion peak of the A3 compound was seen as m/z: 557.64 g/mol. In the MALDI-TOF spectrum of ligand B1, the molecular ion peak was observed at m/z 697.84, corresponding to [M + H]⁺. In the MALDI-TOF spectrum of ligand B3, the molecular ion peak at m/z 1151.0 was assigned to the sodium adduct [M + Na]⁺. Taken together, all spectral data confirm the proposed structures of the synthesized molecules. 3.2 Electronic properties Density functional theory is extensively used to calculate the properties of molecules to describe and explain important chemical concepts of molecular structure and reactivity [ 19 ]. According to the frontier molecular orbital theory (FMO), the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energies are crucial for the chemical reactivity and stability of molecules. The energy gap between HOMO and LUMO is crucial for determining the electrical properties of a molecule, optical polarizability, and global reactivity descriptors such as hardness and softness [ 20 ]. The obtained global reactivity descriptors of the compounds are listed in Table 2 . As seen in Table 2 , the energy value of compound B3 is lower than B1, that is, B3 is more stable than compound B1. Also, the energy value of B3 is lower in the ethanol phase. According to this result, we can say that the compound is more stable in the solvent environment due to the interaction of the solvent and compound. All hardness and softness values ​​are quite close to each other. However, as can be understood from the chemical potential and electrophilic index results, compound B3 is more reactive than compound B1. The chemical potential and electrophilic index results of B3 are − 3.37 eV and 3.43 eV for the ethanol phase. Since the electrophilic index values ​​of the compounds are greater than 1.5 eV, the compounds have an electrophilic structure [ 21 ]. Table 2 Calculated global descriptors and energy values for B1 and B3. B1 B3 Vac. EtOH Vac. EtOH E HOMO (eV) -4.98 -5.01 -5.14 -5.03 E LUMO (eV) -1.58 -1.65 -1.76 -1.72 Hardnesss, η (eV) 1.70 1.68 1.69 1.66 Chemical potential, µ (eV) -3.28 -3.33 -3.45 -3.37 Electrophilic index, ω (eV) 3.16 3.31 3.53 3.43 Softness, S (eV) 0.29 0.30 0.30 0.30 Energy, E (Hartree) -2160.97 -2161.00 -3597.09 -3597.14 The FMO structures are given in Fig. 1 . The HOMO orbitals are mostly located in the terminal group in the B1 molecule and in the center of the B3 molecule. The LUMO orbitals are mostly located in the anchor groups. In order to achieve good performance in a solar cell, the LUMO orbital energy of the molecules need to be higher than TiO 2 and the HOMO orbital energy need to be smaller than the I − /I 3 − potential [ 22 ]. These requirements ensure efficient electron injection and dye regeneration in TiO₂-based DSSCs. As seen in Fig. 1 , both molecules provide these values. Therefore, molecules B1 and B3 can be candidates for DSSC use. As the band gap energy of the compounds decreases, the movement of electrons between the HOMO-LUMO energy levels becomes easier and it is expected that the PCE values ​​of the compound with the lower band gap energy in the produced DSSCs will be higher [ 23 ]. For this reason, it was predicted that the B3 compound would have higher power conversion efficiency than the B1 compound in the study. 3.3. Molecular electrostatic potential (MEP) analysis The molecular electrostatic potential (MEP) surface is a three-dimensional visualized representation of the electrostatic potential on the electron density surface. The color identification of electrostatic potential is in the range of red and blue that red depicts the negative potential areas for electrophilic attacks while blue depicts positive potential areas for the nucleophilic attack [ 23 ]. MEP plots of the molecules are shown in Fig. 2 . For molecules B1 and B3, the electron-rich areas are on the nitrogen atoms of the pyridine rings. The red areas in molecule B3 are more than in B1 because it has two more additional anchor groups. These groups can increase the DSSC properties of the B3 group. The positive potential regions in blue are on the hydrogens of the imidazole groups. During molecular design, electron transfer to titanium dioxide is expected to occur via the 1,10-phenanthroline anchor groups. As seen in Fig. 2 , electrons are most densely concentrated on 1,10-phenanthroline, indicating that electron transfer to titanium dioxide is anchored via nitrogen atoms within the 1,10-phenanthroline structure. 3.4. Photovoltaic performances for DSSC The details of the solar cell fabrication are given in the Device Preparation section. The photocurrent density–voltage (J–V) characteristics of the photovoltaic devices fabricated using sensitizers B1 and B3 under an illumination intensity of 100 mW cm⁻² are shown in Fig. 3 . The photovoltaic parameters such as the short circuit photocurrent density (Jsc), open-circuit voltage (Voc), fill factor (FF) and power conversion efficiency (n), as estimated from these curves, are compiled in Table 3 . Sensitizers B1 and B3 exhibit power conversion efficiencies 0.28% and 0.61%, respectively. Table 3 Photovoltaic parameter values ​​of prepared DSSCs. Dye J sc (mA/cm 2 ) V oc FF η (%) B1 1.37 0.38 0.54 0.28 B3 2.19 0.47 0.59 0.61 The quantum chemical results related to the solar cell performance of these molecules are listed in Table 4 . The relevant formulas are given in the Supplementary materials. To achieve maximum photocurrent generation, a compound must possess a high light-harvesting efficiency (LHE) value [ 24 , 25 ]. As shown in Table 4 , the LHE value of B3 is higher than that of B1, indicating that B3 is more effective as a DSSC sensitizer. This is in accordance with the experimental results. The optical stability of a compound can be determined using excited state lifetime (τ) factor. The longer the excited state lifetime, the greater the optical stability of the compound [ 26 ]. ΔG inj values ​​of the compounds are all negative, which means that excited state electrons of these compounds are spontaneously injected into the conduction band of TiO 2 [ 25 ]. In addition to negative ΔG inj values, ΔG reg values ​​of the compounds are also negative. Therefore, these results confirm the suitability and efficiency of both B1 and B3 as DSSC sensitizers. Table 4 The calculated excited and ground-state oxidation potential (E dye * and E dye ), LHE, ΔG inj , ΔG reg, and excited state lifetime (τ) for B1 and B3 Dye LHE τ (ms) E dye * (eV) E dye (eV) ΔG inj (eV) ΔG reg (eV) B1 0.9923 52.08 5.01 1.32 -2.68 -9.60 B3 0.9977 43.36 5.03 1.41 -2.59 -9.63 4. Conclusion In this study, the B1 and B3 compounds containing a 1,10-phenanthroline anchor group were successfully synthesized. In both structures, electron transfer from the donor groups to the 1,10-phenanthroline anchor group occurs via an imidazole bridge. Among the fabricated DSSC devices, the highest power conversion efficiency (PCE) of 0.61% was achieved with compound B3. The presence of multiple anchor groups in the structure was found to significantly enhance PCE values, as evidenced by the superior performance of B3 compared to B1. Furthermore, the lower E HOMO–LUMO value of B3 supported the observed improvement in electron transfer efficiency and photovoltaic performance. Overall, these results demonstrate that the multi-anchor design strategy effectively improves the electron injection process in DSSCs and contributes to higher device efficiency. This work highlights the potential of 1,10-phenanthroline-based multi-anchor dyes as promising sensitizers for next-generation DSSCs. Future studies will focus on structural optimization and the exploration of alternative π-bridges to further enhance device performance. Declarations Funding This work was supported by Yildiz Technical University Scientific Research Project Coordinator’s FYL-2022-4980 project. Data Availability All data can be requested to corresponding author. Author contributions I.E. and B.O. designed the experiments. S.A. and A.H. performed all theoretical calculations. I.E. and B.O wrote the main manuscript. Conflict of interest The authors have no relevant fnancial or non-fnancial interests to disclose. Ethical approval Not applicable. Consent for publication Not applicable. 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06:38:29","extension":"html","order_by":15,"title":"","display":"","copyAsset":false,"role":"acdc-reference","size":110556,"visible":true,"origin":"","legend":"","description":"","filename":"earlyproof.html","url":"https://assets-eu.researchsquare.com/files/rs-8128370/v1/5e8a9742241b130fada00d18.html"},{"id":96965806,"identity":"01ca0be0-54da-42aa-8b1a-469b9a66a463","added_by":"auto","created_at":"2025-11-28 06:38:32","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":136912,"visible":true,"origin":"","legend":"\u003cp\u003eEnergy levels of the frontier molecular orbitals of compounds B1 and B3.\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-8128370/v1/ab5c912d59e7cd736e049199.png"},{"id":96965858,"identity":"bcecdf67-3941-49dc-a056-a7bffb53104a","added_by":"auto","created_at":"2025-11-28 06:38:37","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":137342,"visible":true,"origin":"","legend":"\u003cp\u003eMEP plots of B1 and B3 compounds\u003cem\u003e.\u003c/em\u003e\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-8128370/v1/0785f90c80ecb792a7f6bb48.png"},{"id":96965851,"identity":"4d8cb620-b045-46fc-ba1c-0585badaa704","added_by":"auto","created_at":"2025-11-28 06:38:36","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":44934,"visible":true,"origin":"","legend":"\u003cp\u003eJ-V curves of DSSCs prepared with B1 and B3 dyes.\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-8128370/v1/528e1e83e14bea183c6b2e52.png"},{"id":105223524,"identity":"3d112a34-dc0f-4451-ad4e-e13830b10514","added_by":"auto","created_at":"2026-03-23 16:08:05","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":1279373,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-8128370/v1/c96f78b5-c4ce-44a4-a2ff-eed79700c235.pdf"},{"id":97136639,"identity":"81dd14cc-6402-4d53-911c-6d3ed6033155","added_by":"auto","created_at":"2025-12-01 09:56:50","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":1769771,"visible":true,"origin":"","legend":"","description":"","filename":"SUPPLEMENTARYINFORMATIONBuseZSAN.docx","url":"https://assets-eu.researchsquare.com/files/rs-8128370/v1/befc6af68ddc245799d9d48e.docx"},{"id":97137836,"identity":"8f6013c9-6387-41e9-9da7-99c5a1bc1dc3","added_by":"auto","created_at":"2025-12-01 09:58:13","extension":"docx","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":54977,"visible":true,"origin":"","legend":"","description":"","filename":"Schemes.docx","url":"https://assets-eu.researchsquare.com/files/rs-8128370/v1/d3014f9626cabd65782082e6.docx"}],"financialInterests":"No competing interests reported.","formattedTitle":"\u003cp\u003eTheoretical Studies and Photovoltaic Performance of 1,10- Phenanthroline Derivative Compound as a Multiple Anchor Group\u003c/p\u003e","fulltext":[{"header":"1. INTRODUCTION","content":"\u003cp\u003eRecently, with the development of science and technology, the design and development of new materials has become more important. The developed materials should be processed in smaller sizes in order to work with high energy efficiency, show high performance, be economical and environmentally friendly and to give good results. Thin film materials have begun to be given priority in technology in order to develop more useful and effective products with less material. In this context, dye-sensitized solar cells (DSSCs), one of the thin-film-based photovoltaic technologies, have attracted particular attention.\u003c/p\u003e\u003cp\u003eDye-sensitized solar cells (DSSCs), first introduced in 1991 by O\u0026rsquo;Regan and Gr\u0026auml;tzel [\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e], are cost-effective and environmentally friendly alternatives to conventional silicon-based photovoltaics. These devices use a mesoporous semiconductor structure to convert sunlight directly into electricity. The mesoporous TiO₂ nanoparticle film, deposited on a transparent conductive substrate, functions as the photoanode and requires an adsorbed organic dye to act as the sensitizer. Charge transfer is enabled by an electrolyte containing a redox mediator-typically the I⁻/I₃⁻ couple-while the circuit is completed by a counter electrode, commonly platinum-coated conductive glass due to its high catalytic activity and stability. The electrolyte solution spreads between the two electrodes and fills the porous structure of the semiconductor, providing electrical contact between them [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eImportant properties are required to make the dye available for TiO\u003csub\u003e2\u003c/sub\u003e -based DSSCs. First, the dye needs to be absorbed primarily in the visible range and the near-infrared region. Secondly, it\u0026rsquo;s lowest unoccupied molecular orbital (LUMO) should be above the conduction band of TiO\u003csub\u003e2\u003c/sub\u003e for the electron injection, and its highest occupied molecular orbital (HOMO) should be lower than the redox potential of the electrolyte for the dye\u0026rsquo;s regeneration [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eOrganic photovoltaic devices, which convert solar energy into electrical energy, have garnered significant interest as part of next-generation solar cell research. Among these technologies, dye-sensitized solar cells (DSSCs) achieve this conversion through sensitizer molecules, some of which are designed using 1,10-phenanthroline derivatives. 1,10-Phenanthroline is used as an anchor group in the sensitizer structure to provide electron transfer in dye-sensitized solar cell (DSSCs). Typically, 1,10-phenanthroline coordinates to a metal center to form metal complexes that act as light-absorbing sensitizers. These complexes absorb sunlight and, through metal-to-ligand charge-transfer (MLCT) excitation, inject electrons into the conduction band of TiO₂. Derivatives of 1,10-phenanthroline can be structurally tuned to improve the stability and overall efficiency of this electron-transfer process [\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e]. Particularly, when used with ruthenium-based complexes, 1,10-phenanthroline derivatives can contribute to achieving highly efficient DSSCs. Although ruthenium (II)-based sensitizers demonstrate high power conversion efficiency, they have several disadvantages, such as being a rare metal, complex synthesis, and purification steps, being toxic and having a high cost. To overcome these drawbacks, metal-free organic sensitizers have been developed and applied in DSSC applications as alternatives to ruthenium (II)-based sensitizers [\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eThe main function of the sensitizer in the DSSC structure is to absorb light and provide electrons to the semiconductor layer TiO\u003csub\u003e2\u003c/sub\u003e. To perform this function effectively, the sensitizer dye must be chemically bonded to the semiconductor surface. In D\u0026ndash;π\u0026ndash;A type sensitizer molecules, anchor groups play a crucial role because they determine both the charge-injection efficiency and the binding strength between the dye and the semiconductor surface [\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e]. In general, carboxylic acid is the most commonly used anchor group, it has good charge injection efficiency and good electron pairing between dyes and semiconductors, but under continuous illumination or the presence of water molecules, carboxyl groups are easily detached from the semiconductor surfaces, which will greatly reduce the dye loading amount and damage the overall performance of the devices [\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e]. To overcome this limitation, many researchers have investigated alternative anchor groups that offer improved stability on TiO₂ surfaces.\u003c/p\u003e\u003cp\u003eIn the literature review, it was found that there were two studies using 1,10-phenanthroline as an anchor group. The first study, employed 1,10-phenanthroline as an anchor group was conducted by Li-Peng Zhang et al. in 2015. They synthesized two new donor-acceptor organic dyes using 1,10-phenanthroline as a linker group. Both dyes were efficiently adsorbed onto the TiO\u003csub\u003e2\u003c/sub\u003e surface via the 1,10-phenanthroline anchor, making them suitable for dye-sensitized solar cells. The resulting DSSCs demonstrated maximum power conversion efficiency (PCE) of 4.04%. This study highlighted that 1,10-phenanthroline is a promising building block for organic dyes that do not contain carboxylic acid, serving as both an acceptor and an anchoring group [\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e]. Another study that two new metal-free organic dyes named S1 and S2 of the 2D-π-2A type were prepared by Hai-Lang Jia et al. in 2019, which were then used as sensitizers in DSSCs. Phenothiazine and carbazole groups were used as electron donors, and 1,10-phenanthroline anchoring groups were added to the acceptors to form the 2D-π-2A type structure. The results showed that both dyes could bind to the Lewis acid sites on the TiO\u003csub\u003e2\u003c/sub\u003e surface through the 1,10-phenanthroline anchoring group. The bidentate configuration helped improve electron injection efficiency and enhance dye adsorption stability. The DSSC based on S1 exhibited a PCE of 4.39%, an open-circuit voltage (V\u003csub\u003eoc\u003c/sub\u003e) of 708 mV, a short-circuit current density (J\u003csub\u003esc\u003c/sub\u003e) of 9.39 mAcm⁻\u0026sup2;, and a fill factor (FF) of 65.99% under AM 1.5G irradiation [\u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e]. These findings indicate that DSSC performance can be further improved through the development of more efficient anchoring groups.\u003c/p\u003e\u003cp\u003eIn this study, a metal-free sensitizer molecule design was made for use in DSSC applications. In the molecules designed as shown in Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan refid=\"Sch2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, it was aimed to increase the PCE value of the solar cell by presenting the electrons coming from a single direction through the donor group to the semiconductor surface through a structure containing 1,10-phenanthroline as a multiple anchor group. The Compounds B1 and B3, which have D-π-A and D-π-3A properties, were designed to be used as sensitizers in DSSC devices. Quantum chemical theoretical calculations were performed for B1 and B3 molecules using the Density Functional Theory (DFT) method in the Gaussian 09 program package. As a result of quantum chemical calculations, the electronic properties of B1 and B3 compounds designed as sensitizers in DSSCs were investigated and analyzed. Structural characterization of the sensitizers was performed by taking FTIR, \u0026sup1;H-NMR, Q-TOF and UV-Vis spectroscopy. The photovoltaic performance of the fabricated solar cells was measured under the Solar Simulator. High PCE values of the DSSC devices were achieved by Current-Voltage (I-V) measurement.\u003c/p\u003e\u003cp\u003e\u003c/p\u003e\u003cp\u003e\u003c/p\u003e"},{"header":"2. EXPERIMENTAL","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e\u003ch2\u003e2.1. Materials and characterization\u003c/h2\u003e\u003cp\u003eAll chemicals and solvents used in this study were of analytical grade and sourced from commercial suppliers. The FTIR spectra were obtained using a Spectrum One Perkin Elmer 1600 FTIR spectrophotometer. \u003csup\u003e1\u003c/sup\u003eH NMR spectra were recorded on a Varian UNITY INOVA 500MHz NMR spectrometer with CDCl\u003csub\u003e3\u003c/sub\u003e and MeOH as the solvent. Absorption spectra were measured using a Shimadzu-2600 UV-Vis spectrophotometer. MALDI-TOF mass spectra were measured on Bruker Microflex LT instrument.\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec4\" class=\"Section2\"\u003e\u003ch2\u003e2.2. Computational method\u003c/h2\u003e\u003cp\u003eIn this study the geometry optimizations of compounds are conducted by using Density Functional Theory B3LYP functional with 6-31g(d,p) level in Gaussian 09 programme [\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e]. The frequency calculations are done after optimization calculations in order to verify the true geometries as global minimum with positive frequencies. Time Dependent Density Functional Theory (TD-DFT) calculations are done with CAM-B3LYP/6-31g(d,p) level for comparison purpose with the experimental ones. In order to obtain \u003csup\u003e1\u003c/sup\u003eH NMR of compounds Gauge Independent Atomic Orbital approach is used. The solvent effect of ethanol is considered by using Conductor Like Polarizable Continuum Model (CPCM) with the same level of theory [\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eThe electronic nature of the compounds are discussed with Molecular Electrostatic Potential (MEP) surface and Frontier Molecular Orbitals (FMO). All the visualizations of compounds are done with GaussView 05 package programme [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eThe reactivity properties of the compounds are discussed using global reactivity descriptors. The dye-sensitized solar cell performance of the compounds is investigated using quantum chemical theoretical calculations (See Supplementary information).\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec5\" class=\"Section2\"\u003e\u003ch2\u003e2.3. Device preparation\u003c/h2\u003e\u003cp\u003eThe preparation of the DSSC devices was carried out as follows: Fluorine-doped tin oxide (FTO) substrates were purchased from Spi Co. Ltd. The substrates were cleaned in an ultrasonic bath using a solution of acetone and isopropanol, and then rinsed with distilled water for 10 minutes. They were dried with nitrogen gas to ensure optimal mechanical contact between the conductive FTO surface and titanium dioxide (TiO\u003csub\u003e2\u003c/sub\u003e), as well as to protect the FTO surface from interaction with the electrolyte. The photoanodes consisting of a 15\u0026ndash;20 \u0026micro;m thick TiO₂ layer were prepared following the procedure described in the literature [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e]. The TiO₂ paste was coated onto the cleaned FTO substrates using the doctor blade technique, wherein a metal strip was used to evenly spread the paste. The coated TiO₂ layer was subsequently heated to 400\u0026deg;C in air and sintered at this temperature for 3 hours. After sintering step, the TiO\u003csub\u003e2\u003c/sub\u003e film was stained by immersing into 1x10\u003csup\u003e\u0026minus;\u0026thinsp;4\u003c/sup\u003e M dye solution containing B1 and B3 at room temperature for 24 h, respectively. Finally, a platinized FTO counter electrode was manually pressed onto the assembled device. The platinized FTO substrate was prepared by immersing it in an H₂PtCl₄ solution and subsequently heating it at 450\u0026deg;C for 10 minutes.\u003c/p\u003e\u003cp\u003eAfter drying under an air stream, the sensitized TiO₂ electrode was sandwiched with a thermally platinized counter electrode separated and sealed. The electrolyte solution, composed of 0.5 M potassium iodide and 0.05 M iodine dissolved in pure ethylene glycol, was prepared following the procedure outlined by Smestad [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e]. The electrolyte was injected into the gap between the electrodes by capillarity. The active area of the devices, determined by the overlapping regions of the anode and cathode, was set to 1 cm\u0026sup2;. The photovoltaic performance was determined under simulated sunlight. The current density versus voltage (J-V) characteristics of the cells were measured both in the dark and under simulated ABET 1.5 G solar illumination by using a Keithley 2400 Digital Source Meter at room temperature.\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec6\" class=\"Section2\"\u003e\u003ch2\u003e2.4. Synthesis\u003c/h2\u003e\u003cp\u003e5-Nitro-1,10-phenanthroline [\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e], 5-Nitro-6-amino-1,10-phenanthroline [\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e], 5,6-Diamino-1,10-phenanthroline [\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e] and Tris(4-bromo phenyl) amine [\u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e] were synthesized according to the literature procedures.\u003c/p\u003e\u003cdiv id=\"Sec7\" class=\"Section3\"\u003e\u003ch2\u003e2.4.1. Synthesis of 4'-[bis(4-bromophenyl)amino]-[1,1'-biphenyl]-4-carbaldehyde (A1-Br\u003csub\u003e2\u003c/sub\u003e)\u003c/h2\u003e\u003cp\u003eTris(4-bromophenyl) amine (96.0 mg, 0.20 mmol), 4-formylphenylboronic acid (30.0 mg, 0.20 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.9 mg, 0.0033 mmol) were stirred at room temperature in 1,4-dioxane (20.0 mL) under an argon atmosphere. A 1.0 M aqueous Na₂CO₃ solution (5 mL) was added dropwise to the reaction mixture. The reaction mixture was heated to reflux at 100\u0026deg;C and stirred for 24 hours. After cooling to room temperature, the reaction mixture was extracted with CHCl₃ (3 \u0026times; 10 mL). The organic phase was washed with water (5.0 mL), 1 M HCl (5.0 mL), and brine (5.0 mL), dried over anhydrous MgSO₄, filtered, and evaporated under vacuum. The crude product was obtained as a yellow powder (C\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e17\u003c/sub\u003eBr\u003csub\u003e2\u003c/sub\u003eNO: 507.217 g/mol)(Scheme SI.1). FTIR (ATR, cm⁻\u0026sup1;): 3061 cm⁻\u0026sup1; (Ar), 1682 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;O), 1484 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;C). \u0026sup1;H-NMR (500 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e, ppm) δ 10.02 (s, 1H), 7.93 (d, 2H), 7.86 (d, 2H), 7.74 (d, 2H), 7.65 (d, 4H), 7.32 (d, 2H), 6.93 (d, 4H) (SI.13).\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec8\" class=\"Section3\"\u003e\u003ch2\u003e2.4.2. Synthesis of 4\u0026rsquo;-[bis({[1,1\u0026rsquo;-biphenyl]-4-yl})amino]-[1,1\u0026rsquo;-biphenyl]-4-carbaldehyde (A1)\u003c/h2\u003e\u003cp\u003eA1-Br\u003csub\u003e2\u003c/sub\u003e (101.4 mg, 0.20 mmol), phenylboronic acid pinacol ester (40.0 mg, 0.20 mmol), and tetrakis(triphenylphosphine)palladium(0) (7.7 mg, 0.0066 mmol) were stirred at room temperature in 1,4-dioxane (50.0 mL) under an argon atmosphere. A 1.0 M aqueous solution of Na₂CO₃ (5.0 mL) was added dropwise to the mixture. The mixture was heated to reflux at 100\u0026deg;C and stirred for 48 hours. The reaction mixture was cooled to room temperature and extracted with CHCl₃ (3 \u0026times; 10 mL). The organic phase was washed with water (5.0 mL), 1 M HCl (5.0 mL), and brine (5.0 mL), dried over anhydrous MgSO₄, filtered, and evaporated under vacuum. The crude product was obtained as a yellow powder (C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e27\u003c/sub\u003eNO: 501.62 g/mol). FTIR (ATR, cm⁻\u0026sup1;): 3058 cm⁻\u0026sup1; (Ar), 1692 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;O), 1483 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;C) (Figure SI.9). UV-Vis (max., nm.): 220, 355. (Figure SI.5). \u0026sup1;H-NMR (500 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e, ppm) δ 10.12 (s, 1H), 8.03 (d, 2H), 7.95 (d, 2H), 7.83 (d, 6H), 7.75 (d, 6H), 7.54 (d, 4H), 7.17 (t, 4H), 7.10 (t, 2H) (Figure SI.14).\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec9\" class=\"Section3\"\u003e\u003ch2\u003e2.4.3. Synthesis of 4\u0026rsquo;-[bis({4\u0026rsquo;-formyl-[1,1\u0026rsquo;-biphenyl]-4-yl})amino]-[1,1\u0026rsquo;-biphenyl]-4-carbaldehyde (A3)\u003c/h2\u003e\u003cp\u003eTris(4-bromo phenyl) amine (32.0 mg, 0.0667 mmol), 4-formylphenylboronic acid (30.0 mg, 0.20 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.9 mg, 0.0033 mmol) were stirred at room temperature in 1,4-dioxane (20.0 mL) under an argon atmosphere. A 1.0 M aqueous solution of Na₂CO₃ (5.0 mL) was added dropwise to the mixture. The mixture was heated to reflux at 100\u0026deg;C and stirred for 48 hours. The reaction mixture was cooled to room temperature and extracted with CHCl₃ (10.0 mL). The organic phase was washed with water (5.0 mL), 1 M HCl (5.0 mL), and brine (5.0 mL), dried over anhydrous MgSO₄, filtered, and evaporated under vacuum. The crude product was obtained as a yellow powder (C\u003csub\u003e39\u003c/sub\u003eH\u003csub\u003e27\u003c/sub\u003eNO\u003csub\u003e3\u003c/sub\u003e: 557.64 g/mol). Melting point: 230\u0026deg;C, Yield: 17 mg (54%). FTIR (ATR, cm⁻\u0026sup1;): 3069 cm⁻\u0026sup1; (Ar), 1695 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;O), 1485 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;C) (Figure SI.10). UV-Vis (max., nm.): 220, 270, 385. (Figure SI.6). \u0026sup1;H-NMR (500 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e, ppm) δ 10.02 (s, 3H), 7.93 (d, 6H), 7.74 (d, 6H), 7.32 (d, 6H), 6.93 (d, 6H) (SI.15). Q-TOF ESI MS m/z [M+]: 557.18 g/mol, (Figure SI.18) [\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e].\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec10\" class=\"Section3\"\u003e\u003ch2\u003e2.4.4. Synthesis of N,N-bis({[1,1\u0026rsquo;-biphenyl]-4-yl})-4\u0026rsquo;-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}-[1,1\u0026rsquo;-biphenyl]-4-amine (B1)\u003c/h2\u003e\u003cp\u003e5,6-Diamino-1,10-phenanthroline (30.0 mg, 0.142 mmol) was dissolved in 20.0 mL of anhydrous ethanol, and the A1 compound (71.2 mg, 0.0473 mmol) dissolved in 30.0 mL of anhydrous ethanol, was added dropwise. The reaction mixture was stirred under reflux in argon atmosphere for 12 hours. The solvent was evaporated to one-third of its initial volume using a rotary evaporator, and then petroleum ether was added at room temperature. When the solution cooled to room temperature, a yellow precipitate was obtained. The precipitate was filtered and then recrystallized from a 2:1 n-hexane/ethyl acetate mixture. (C\u003csub\u003e49\u003c/sub\u003eH\u003csub\u003e33\u003c/sub\u003eN\u003csub\u003e5\u003c/sub\u003e: 691.82 g/mol). FTIR (ATR, cm⁻\u0026sup1;): 3285 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e (N-H), 3070 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e (aromatic C-H), 1577 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e (C\u0026thinsp;=\u0026thinsp;N), 1484 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e (C\u0026thinsp;=\u0026thinsp;C) (Figure SI.11). \u003csup\u003e1\u003c/sup\u003eH-NMR (500 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e, ppm) δ 9.58 (d, 2H), 9.26 (d, 2H), 8.95 (s,1H), 8.18 (d, 2H), 7.77 (d, 2H), 7.57 (d, 4H), 7.29 (d, 6H), 7.02 (m, 2H), 6.96 (m, 4H), 6.91 (m, 2H), 6.85 (d, 6H) (SI.16). MALDI-TOF [M\u0026thinsp;+\u0026thinsp;1]\u0026thinsp;+\u0026thinsp;5H 697.84 g/mol (Figure SI.19).\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec11\" class=\"Section3\"\u003e\u003ch2\u003e2.4.5. Synthesis of 4\u0026rsquo;-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}-N,N-bis(4\u0026rsquo;-{1H-imidazo[4,5-f]1,10-phenanthrolin-2-yl}-[1,1\u0026rsquo;-biphenyl]-4-yl)-[1,1\u0026rsquo;-biphenyl]-4-amine(B3)\u003c/h2\u003e\u003cp\u003e5,6-Diamino-1,10-phenanthroline (30.0 mg, 0.142 mmol) was dissolved in 30.0 mL of anhydrous ethanol, and the A3 compound (26.4 mg, 0.0473 mmol) dissolved in 10.0 mL of anhydrous ethanol, was added dropwise. The reaction mixture was stirred under reflux in argon atmosphere for 12 hours. The solvent was evaporated to one-third of its initial volume using a rotary evaporator, and petroleum ether was added at room temperature. When the solution cooled to room temperature, a yellow precipitate was obtained. The precipitate was filtered and then recrystallized from a 2:1 n-hexane/ethyl acetate mixture. (C\u003csub\u003e75\u003c/sub\u003eH\u003csub\u003e45\u003c/sub\u003eN\u003csub\u003e13\u003c/sub\u003e: 1128 g/mol). Melting point: 340\u0026deg;C, Yield: 27 mg (52%). FTIR (ATR, cm⁻\u0026sup1;): 3290 cm⁻\u0026sup1; (N-H), 3080 cm⁻\u0026sup1; (Aromatic), 1595 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;N), 1470 cm⁻\u0026sup1; (C\u0026thinsp;=\u0026thinsp;C) (Figure SI.12).\u003c/p\u003e\u003cp\u003e\u0026sup1;H-NMR (500 MHz, MeOH, ppm): δ 9.67 (s, 3H), 8.88 (d, 3H), 8.83 (d, 3H), 8.30 (dd, 6H), 7.69 (d, 6H), 7.55 (d, 6H), 7.45 (td, 6H), 6.92 (d, 6H), 6.83 (d, 6H) (SI.17). MALDI-TOF [M\u0026thinsp;+\u0026thinsp;1]Na⁺ 1151 g/mol (Figure SI.20).\u003c/p\u003e\u003c/div\u003e\u003c/div\u003e"},{"header":"3. Results and Discussion","content":"\u003cdiv id=\"Sec13\" class=\"Section2\"\u003e\u003ch2\u003e3.1. Characterization\u003c/h2\u003e\u003cp\u003eAs seen in Schemes \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan refid=\"Sch2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, compounds B1 and B3 were synthesized purely and in good yields. In the synthetic procedure, the tris(4-bromophenyl)amine, obtained by the bromination of triphenylamine, was first reacted with 4-formylphenylboronic acid in appropriate molar ratios to afford the intermediates A1 and A3, as shown in Schemes SI.1 and SI.2 in the Supplementary Information. Subsequently, compounds A1 and A3 were separately reacted with 5,6-diamino-1,10-phenanthroline to afford compounds B1 and B3, respectively, as shown in Schemes SI.3 and SI.4. The resulting compounds were purified using a variety of methods and characterized in their pure form by FTIR, UV-Vis, \u003csup\u003e1\u003c/sup\u003eH-NMR, and MALDI-MS spectroscopy.\u003c/p\u003e\u003cp\u003eIn the UV-Vis spectrum analysis of the synthesized compounds B1 and B3, π-π* transitions were observed in the range of 250\u0026ndash;350 nm, while n-π* transitions appeared between 350\u0026ndash;400 nm, as shown in Figures SI.7 and SI.8. The calculated TD-DFT results are given in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e. As seen in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e, the main transition of compound B1 occurs from HOMO to LUMO with a contribution of 53.79%. The maximum wavelength of this transition is 336.26 nm and this result is in good agreement with the experimental one, the percentage error is 0.51%. For compound B3, the main transition occurs from HOMO to LUMO with a contribution of 55.90%. The maximum wavelength of this transition is 342.74 nm, and this result is in good agreement with the experimental data, with a percentage error of 3.18%. Another important transition occurs between HOMO-1 and LUMO. Spectral calculation results for orbital contributions are given in Figures SI.3 and SI.4.\u003c/p\u003e\u003cp\u003eWhen the FTIR spectra of compounds B1 (Figures SI.11) and B3 (Figures SI.12) were evaluated, characteristic vibration bands belonging to the -NH group in the imidazole ring were observed at 3285\u0026ndash;3290 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 3526\u0026ndash;3527 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e for the experimental and calculated, respectively. In addition, the vibration bands belonging to the C\u0026thinsp;=\u0026thinsp;O group seen at 1692 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 1695 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e in the structure of compounds A1 (Figures SI.9) and A3 (Figures SI.10) and the vibration bands belonging to the -NH\u003csub\u003e2\u003c/sub\u003e group seen at 3370 and 3267 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e in the structure of 5,6-diamino-1,10-phenanthroline are not seen in the FTIR spectrum of molecules B1 and B3. This supports the formation of the imidazole ring in the structure of compounds B1 and B3. The comparison of calculated and experimental frequencies is given in Table SI.1. As seen in Table SI.1, the frequencies are compatible with each other.\u003c/p\u003e\u003cp\u003e\u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab1\" border=\"1\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eCalculated wavelengths (nm), excitation energies (eV), oscillator strength, and orbital contributions for compound B1 and B3.\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ccolgroup cols=\"6\"\u003e\u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e\u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e\u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/th\u003e\u003cth align=\"left\" colname=\"c2\"\u003e\u003cp\u003eΛ (nm)\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c3\"\u003e\u003cp\u003eE\u003csub\u003eex\u003c/sub\u003e (eV)\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c4\"\u003e\u003cp\u003ef\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c5\"\u003e\u003cp\u003eOrbital Contribution\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c6\"\u003e\u003cp\u003eλexp (nm)\u003c/p\u003e\u003c/th\u003e\u003c/tr\u003e\u003c/thead\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eB1\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e336.26\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e3.69\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e2.12\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:\\to\\:\\)\u003c/span\u003e\u003c/span\u003e LUMO (53.79%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e\u003cp\u003e338\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO-1 \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:\\to\\:\\)\u003c/span\u003e\u003c/span\u003e LUMO (17.50%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO-1 \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:\\to\\:\\)\u003c/span\u003e\u003c/span\u003e LUMO\u0026thinsp;+\u0026thinsp;4 (2.62%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO \u0026rarr; LUMO\u0026thinsp;+\u0026thinsp;1 (4.87%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO \u0026rarr; LUMO\u0026thinsp;+\u0026thinsp;2 (7.67%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO\u0026thinsp;+\u0026thinsp;1 \u0026rarr; LUMO\u0026thinsp;+\u0026thinsp;4 (4.50%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eB3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e342.74\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e3.62\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e2.64\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:\\to\\:\\)\u003c/span\u003e\u003c/span\u003e LUMO (55.90%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e\u003cp\u003e354\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO-3 \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:\\to\\:\\)\u003c/span\u003e\u003c/span\u003e LUMO\u0026thinsp;+\u0026thinsp;1 (2.04%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO-2 \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:\\to\\:\\)\u003c/span\u003e\u003c/span\u003e LUMO\u0026thinsp;+\u0026thinsp;1 (5.58%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO-1 \u0026rarr; LUMO\u0026thinsp;+\u0026thinsp;2 (7.95%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO \u0026rarr; LUMO\u0026thinsp;+\u0026thinsp;3 (2.47%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO \u0026rarr; LUMO\u0026thinsp;+\u0026thinsp;6 (3.74%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e\u003cp\u003eHOMO \u0026rarr; LUMO\u0026thinsp;+\u0026thinsp;11 (4.14%)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/colgroup\u003e\u003c/table\u003e\u003c/div\u003e\u003c/p\u003e\u003cp\u003eThe aldehyde proton of A1 (10.12 ppm) and the \u0026ndash;NH₂ protons of 5,6-diamino-1,10-phenanthroline (4.4 ppm) disappeared in the \u0026sup1;H-NMR spectrum of B1. It was observed that a singlet -NH proton belonging to the imidazole ring was formed at 8.95 ppm in the structure. The aldehyde proton of A3 (10.02 ppm) and the \u0026ndash;NH₂ protons of 5,6-diamino-1,10-phenanthroline (4.4 ppm) disappeared in the \u0026sup1;H-NMR spectrum of B3. It was observed that a singlet -NH proton belonging to the imidazole ring was formed at 9.67 ppm in the structure. Also, the calculated \u003csup\u003e1\u003c/sup\u003eH-NMR results are in good agreement with the experimental results (Table SI.2).\u003c/p\u003e\u003cp\u003eIn the Q-toff spectrum, the molecular ion peak of the A3 compound was seen as m/z: 557.64 g/mol. In the MALDI-TOF spectrum of ligand B1, the molecular ion peak was observed at m/z 697.84, corresponding to [M\u0026thinsp;+\u0026thinsp;H]⁺. In the MALDI-TOF spectrum of ligand B3, the molecular ion peak at m/z 1151.0 was assigned to the sodium adduct [M\u0026thinsp;+\u0026thinsp;Na]⁺. Taken together, all spectral data confirm the proposed structures of the synthesized molecules.\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec14\" class=\"Section2\"\u003e\u003ch2\u003e3.2 Electronic properties\u003c/h2\u003e\u003cp\u003eDensity functional theory is extensively used to calculate the properties of molecules to describe and explain important chemical concepts of molecular structure and reactivity [\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e]. According to the frontier molecular orbital theory (FMO), the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energies are crucial for the chemical reactivity and stability of molecules. The energy gap between HOMO and LUMO is crucial for determining the electrical properties of a molecule, optical polarizability, and global reactivity descriptors such as hardness and softness [\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e]. The obtained global reactivity descriptors of the compounds are listed in Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e.\u003c/p\u003e\u003cp\u003eAs seen in Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, the energy value of compound B3 is lower than B1, that is, B3 is more stable than compound B1. Also, the energy value of B3 is lower in the ethanol phase. According to this result, we can say that the compound is more stable in the solvent environment due to the interaction of the solvent and compound. All hardness and softness values ​​are quite close to each other. However, as can be understood from the chemical potential and electrophilic index results, compound B3 is more reactive than compound B1. The chemical potential and electrophilic index results of B3 are \u0026minus;\u0026thinsp;3.37 eV and 3.43 eV for the ethanol phase. Since the electrophilic index values ​​of the compounds are greater than 1.5 eV, the compounds have an electrophilic structure [\u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e21\u003c/span\u003e].\u003c/p\u003e\u003cp\u003e\u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab2\" border=\"1\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eCalculated global descriptors and energy values for B1 and B3.\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ccolgroup cols=\"5\"\u003e\u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e\u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e\u0026nbsp;\u003c/th\u003e\u003cth align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e\u003cp\u003eB1\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e\u003cp\u003eB3\u003c/p\u003e\u003c/th\u003e\u003c/tr\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c2\"\u003e\u003cp\u003eVac.\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c3\"\u003e\u003cp\u003eEtOH\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c4\"\u003e\u003cp\u003eVac.\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c5\"\u003e\u003cp\u003eEtOH\u003c/p\u003e\u003c/th\u003e\u003c/tr\u003e\u003c/thead\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eE\u003csub\u003eHOMO\u003c/sub\u003e (eV)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e-4.98\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e-5.01\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e-5.14\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e-5.03\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eE\u003csub\u003eLUMO\u003c/sub\u003e (eV)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e-1.58\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e-1.65\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e-1.76\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e-1.72\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eHardnesss, η (eV)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e1.70\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e1.68\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e1.69\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e1.66\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eChemical potential, \u0026micro; (eV)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e-3.28\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e-3.33\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e-3.45\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e-3.37\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eElectrophilic index, ω (eV)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e3.16\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e3.31\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e3.53\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e3.43\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eSoftness, S (eV)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e0.29\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e0.30\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e0.30\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e0.30\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003eEnergy, E (Hartree)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e-2160.97\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e-2161.00\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e-3597.09\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e-3597.14\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/colgroup\u003e\u003c/table\u003e\u003c/div\u003e\u003c/p\u003e\u003cp\u003eThe FMO structures are given in Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e. The HOMO orbitals are mostly located in the terminal group in the B1 molecule and in the center of the B3 molecule. The LUMO orbitals are mostly located in the anchor groups. In order to achieve good performance in a solar cell, the LUMO orbital energy of the molecules need to be higher than TiO\u003csub\u003e2\u003c/sub\u003e and the HOMO orbital energy need to be smaller than the I\u003csup\u003e\u0026minus;\u003c/sup\u003e/I\u003csub\u003e3\u003c/sub\u003e\u003csup\u003e\u0026minus;\u003c/sup\u003e potential [\u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e]. These requirements ensure efficient electron injection and dye regeneration in TiO₂-based DSSCs. As seen in Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e, both molecules provide these values. Therefore, molecules B1 and B3 can be candidates for DSSC use.\u003c/p\u003e\u003cp\u003e\u003c/p\u003e\u003cp\u003eAs the band gap energy of the compounds decreases, the movement of electrons between the HOMO-LUMO energy levels becomes easier and it is expected that the PCE values ​​of the compound with the lower band gap energy in the produced DSSCs will be higher [\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e]. For this reason, it was predicted that the B3 compound would have higher power conversion efficiency than the B1 compound in the study.\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec15\" class=\"Section2\"\u003e\u003ch2\u003e3.3. Molecular electrostatic potential (MEP) analysis\u003c/h2\u003e\u003cp\u003eThe molecular electrostatic potential (MEP) surface is a three-dimensional visualized representation of the electrostatic potential on the electron density surface. The color identification of electrostatic potential is in the range of red and blue that red depicts the negative potential areas for electrophilic attacks while blue depicts positive potential areas for the nucleophilic attack [\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e]. MEP plots of the molecules are shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e. For molecules B1 and B3, the electron-rich areas are on the nitrogen atoms of the pyridine rings. The red areas in molecule B3 are more than in B1 because it has two more additional anchor groups. These groups can increase the DSSC properties of the B3 group. The positive potential regions in blue are on the hydrogens of the imidazole groups. During molecular design, electron transfer to titanium dioxide is expected to occur via the 1,10-phenanthroline anchor groups. As seen in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, electrons are most densely concentrated on 1,10-phenanthroline, indicating that electron transfer to titanium dioxide is anchored via nitrogen atoms within the 1,10-phenanthroline structure.\u003c/p\u003e\u003cp\u003e\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec16\" class=\"Section2\"\u003e\u003ch2\u003e3.4. Photovoltaic performances for DSSC\u003c/h2\u003e\u003cp\u003eThe details of the solar cell fabrication are given in the Device Preparation section. The photocurrent density\u0026ndash;voltage (J\u0026ndash;V) characteristics of the photovoltaic devices fabricated using sensitizers B1 and B3 under an illumination intensity of 100 mW cm⁻\u0026sup2; are shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e.\u003c/p\u003e\u003cp\u003e\u003c/p\u003e\u003cp\u003eThe photovoltaic parameters such as the short circuit photocurrent density (Jsc), open-circuit voltage (Voc), fill factor (FF) and power conversion efficiency (n), as estimated from these curves, are compiled in Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e. Sensitizers B1 and B3 exhibit power conversion efficiencies 0.28% and 0.61%, respectively.\u003c/p\u003e\u003cp\u003e\u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab3\" border=\"1\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 3\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003ePhotovoltaic parameter values ​​of prepared DSSCs.\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ccolgroup cols=\"5\"\u003e\u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e\u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c1\"\u003e\u003cp\u003eDye\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c2\"\u003e\u003cp\u003eJ\u003csub\u003esc\u003c/sub\u003e \u003cem\u003e(mA/cm\u003c/em\u003e\u003csup\u003e\u003cem\u003e2\u003c/em\u003e\u003c/sup\u003e\u003cem\u003e)\u003c/em\u003e\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c3\"\u003e\u003cp\u003eV\u003csub\u003eoc\u003c/sub\u003e\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c4\"\u003e\u003cp\u003eFF\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c5\"\u003e\u003cp\u003e\u003cem\u003eη (%)\u003c/em\u003e\u003c/p\u003e\u003c/th\u003e\u003c/tr\u003e\u003c/thead\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003e\u003cb\u003eB1\u003c/b\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e1.37\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e0.38\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e0.54\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e0.28\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003e\u003cb\u003eB3\u003c/b\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e2.19\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e0.47\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e0.59\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e0.61\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/colgroup\u003e\u003c/table\u003e\u003c/div\u003e\u003c/p\u003e\u003cp\u003eThe quantum chemical results related to the solar cell performance of these molecules are listed in Table\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e. The relevant formulas are given in the Supplementary materials. To achieve maximum photocurrent generation, a compound must possess a high light-harvesting efficiency (LHE) value [\u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e24\u003c/span\u003e, \u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e]. As shown in Table\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e, the LHE value of B3 is higher than that of B1, indicating that B3 is more effective as a DSSC sensitizer. This is in accordance with the experimental results. The optical stability of a compound can be determined using excited state lifetime (τ) factor. The longer the excited state lifetime, the greater the optical stability of the compound [\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e]. ΔG\u003csub\u003einj\u003c/sub\u003e values ​​of the compounds are all negative, which means that excited state electrons of these compounds are spontaneously injected into the conduction band of TiO\u003csub\u003e2\u003c/sub\u003e [\u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e]. In addition to negative ΔG\u003csub\u003einj\u003c/sub\u003e values, ΔG\u003csub\u003ereg\u003c/sub\u003e values ​​of the compounds are also negative. Therefore, these results confirm the suitability and efficiency of both B1 and B3 as DSSC sensitizers.\u003c/p\u003e\u003cp\u003e\u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab4\" border=\"1\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 4\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eThe calculated excited and ground-state oxidation potential (E\u003csub\u003edye\u003c/sub\u003e\u003csup\u003e*\u003c/sup\u003e and E\u003csub\u003edye\u003c/sub\u003e), LHE, ΔG\u003csub\u003einj\u003c/sub\u003e, ΔG\u003csub\u003ereg,\u003c/sub\u003e and excited state lifetime (τ) for B1 and B3\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ccolgroup cols=\"7\"\u003e\u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e\u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e\u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c1\"\u003e\u003cp\u003eDye\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c2\"\u003e\u003cp\u003eLHE\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c3\"\u003e\u003cp\u003eτ (ms)\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c4\"\u003e\u003cp\u003eE\u003csub\u003edye\u003c/sub\u003e\u003csup\u003e*\u003c/sup\u003e (eV)\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c5\"\u003e\u003cp\u003eE\u003csub\u003edye\u003c/sub\u003e (eV)\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c6\"\u003e\u003cp\u003eΔG\u003csub\u003einj\u003c/sub\u003e (eV)\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colname=\"c7\"\u003e\u003cp\u003eΔG\u003csub\u003ereg\u003c/sub\u003e (eV)\u003c/p\u003e\u003c/th\u003e\u003c/tr\u003e\u003c/thead\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003e\u003cb\u003eB1\u003c/b\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e0.9923\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e52.08\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e5.01\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e1.32\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e\u003cp\u003e-2.68\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c7\"\u003e\u003cp\u003e-9.60\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e\u003cp\u003e\u003cb\u003eB3\u003c/b\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e\u003cp\u003e0.9977\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e\u003cp\u003e43.36\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e\u003cp\u003e5.03\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e\u003cp\u003e1.41\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e\u003cp\u003e-2.59\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"char\" char=\".\" colname=\"c7\"\u003e\u003cp\u003e-9.63\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/colgroup\u003e\u003c/table\u003e\u003c/div\u003e\u003c/p\u003e\u003c/div\u003e"},{"header":"4. Conclusion","content":"\u003cp\u003eIn this study, the B1 and B3 compounds containing a 1,10-phenanthroline anchor group were successfully synthesized. In both structures, electron transfer from the donor groups to the 1,10-phenanthroline anchor group occurs via an imidazole bridge. Among the fabricated DSSC devices, the highest power conversion efficiency (PCE) of 0.61% was achieved with compound B3. The presence of multiple anchor groups in the structure was found to significantly enhance PCE values, as evidenced by the superior performance of B3 compared to B1. Furthermore, the lower E\u003csub\u003eHOMO\u0026ndash;LUMO\u003c/sub\u003e value of B3 supported the observed improvement in electron transfer efficiency and photovoltaic performance.\u003c/p\u003e\u003cp\u003eOverall, these results demonstrate that the multi-anchor design strategy effectively improves the electron injection process in DSSCs and contributes to higher device efficiency. This work highlights the potential of 1,10-phenanthroline-based multi-anchor dyes as promising sensitizers for next-generation DSSCs. Future studies will focus on structural optimization and the exploration of alternative π-bridges to further enhance device performance.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eFunding\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThis work was supported by Yildiz Technical University Scientific Research Project Coordinator\u0026rsquo;s FYL-2022-4980 project.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData Availability\u003c/strong\u003e All data can be requested to corresponding author.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthor contributions\u0026nbsp;\u003c/strong\u003eI.E. and B.O. designed the experiments. S.A. and A.H. performed all theoretical calculations. I.E. and B.O wrote the main manuscript.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflict of interest\u003c/strong\u003e The authors have no relevant fnancial or non-fnancial interests to disclose.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eEthical approval\u003c/strong\u003e Not applicable.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConsent for publication\u003c/strong\u003e Not applicable.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eHuman or animal rights\u003c/strong\u003e Not applicable\u0026nbsp;\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eO\u0026rsquo;Regan B, Gr\u0026auml;tzel M (1991) A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO₂ films. \u003cem\u003eNature\u003c/em\u003e 353:737\u0026ndash;740. http://dx.doi.org/10.1038/353737a0\u003c/li\u003e\n\u003cli\u003eGr\u0026auml;tzel M (2003) Dye-sensitized solar cells. \u003cem\u003eJ Photochem Photobiol C Photochem Rev\u003c/em\u003e 4:145\u0026ndash;153. http://dx.doi.org/10.1016/S1389-5567(03)00026-1\u003c/li\u003e\n\u003cli\u003eKrishna JVS, Mrinalini M, Prasanthkumar S, Giribabu L (2019) Recent advances on porphyrin dyes for dye-sensitized solar cells. 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Cells\u003c/em\u003e \u003cem\u003e55\u003c/em\u003e:157\u0026ndash;178. https://doi.org/10.1016/S0927-0248(98)00056-7.\u003c/li\u003e\n\u003cli\u003eSmith GF, Cagle W (1947) The Improved Synthesis of 5-Nitro-1,10-Phenanthroline. \u003cem\u003eThe Journal of Organic Chemistry 12(6):781\u0026ndash;784.\u003c/em\u003e https://doi.org/10.1021/jo01170a007.\u003c/li\u003e\n\u003cli\u003eBolger J, Gourdon A, Ishow E, Launay JP (1996) Mononuclear and Binuclear Tetrapyrido[3,2- a:2\u0026prime;,3\u0026prime;- c:3\u0026prime;\u0026prime;,2\u0026prime;\u0026prime;- h:2\u0026prime;\u0026prime;\u0026prime;,3\u0026prime;\u0026prime;\u0026prime;- j]Phenazine (tpphz) Ruthenium and Osmium Complexes. \u003cem\u003eInorg. 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Chem.\u003c/em\u003e \u003cem\u003e80\u003c/em\u003e(19):9641\u0026ndash;9651. https://doi.org/10.1021/acs.joc.5b01636.\u003c/li\u003e\n\u003cli\u003eElango M, Parthasarathi R, Narayanan GK, Sabeelullah AM, Sarkar U, Venkatasubramaniyan NS, Subramanian V, Chattaraj PK (2005) Relationship Between Electrophilicity Index, Hammett Constant and Nucleus-Independent Chemical Shift. \u003cem\u003eJ. Chem. Sci.\u003c/em\u003e \u003cem\u003e117\u003c/em\u003e(1):61\u0026ndash;65. https://doi.org/10.1007/BF02704362.\u003c/li\u003e\n\u003cli\u003eAydoğdu S, Hatipoğlu A, Erdoğmuş A (2022) Metallophthalocyanines for PDT Applications: A DFT Study. Journal of Computational Biophysics and Chemistry Volume 21, Issue 5:599\u0026ndash;609. https://doi.org/10.1142/S2737416522500235\u003c/li\u003e\n\u003cli\u003eDomingo LR, P\u0026eacute;rez P (2011) The Nucleophilicity N Index in Organic Chemistry. \u003cem\u003eOrg. Biomol. Chem.\u003c/em\u003e \u003cem\u003e9\u003c/em\u003e(20):7168. https://doi.org/10.1039/c1ob05856h.\u003c/li\u003e\n\u003cli\u003eUrbani M, Ragoussi ME, Nazeeruddin MK, Torres T (2019) Phthalocyanines for Dye-Sensitized Solar Cells. \u003cem\u003eCoord. Chem. Rev.\u003c/em\u003e \u003cem\u003e381\u003c/em\u003e:1\u0026ndash;64. https://doi.org/10.1016/j.ccr.2018.10.007.\u003c/li\u003e\n\u003cli\u003eErden I, Hatipoglu A, Cebeci C, Aydogdu S (2020) Synthesis of D-\u0026pi;-A Type 4,5-Diazafluorene Ligands and Ru (II) Complexes and Theoretical Approaches for Dye-Sensitive Solar Cell Applications. \u003cem\u003eJournal of Molecular Structure\u003c/em\u003e \u003cem\u003e1201\u003c/em\u003e:127202. https://doi.org/10.1016/j.molstruc.2019.127202.\u003c/li\u003e\n\u003cli\u003eSamiee S, Hossienpour P (2019) Tuning the Electronic and Optical Properties of Pt(diimine)(dithiolate) Complexes Through Different Anchoring Groups; A DFT/TD-DFT Study. \u003cem\u003eInorganica Chim. Acta\u003c/em\u003e \u003cem\u003e494\u003c/em\u003e:13\u0026ndash;20. https://doi.org/10.1016/j.ica.2019.05.006.\u003c/li\u003e\n\u003cli\u003eBritel O, Fitri A, Benjelloun AT, Benzakour M, Mcharfi M (2023) New Carbazole-Based Dyes for Efficient Dye-Sensitized Solar Cells: A DFT Insight. \u003cem\u003eStruct. Chem.\u003c/em\u003e \u003cem\u003e34\u003c/em\u003e(5):1827\u0026ndash;1842. https://doi.org/10.1007/s11224-023-02122-2.\u003c/li\u003e\n\u003cli\u003eY\u0026uuml;zer AC, Kurtay G, Ince T, Yurtdaş S, Harputlu E, Ocakoğlu K, G\u0026uuml;ll\u0026uuml; M, Tozlu C, Ince M (2021) Solution-Processed Small-Molecule Organic Solar Cells Based on Non-Aggregated Zinc Phthalocyanine Derivatives: A Comparative Experimental and Theoretical Study. \u003cem\u003eMater. Sci. Semicond. Process.\u003c/em\u003e \u003cem\u003e129\u003c/em\u003e:105777. https://doi.org/10.1016/j.mssp.2021.105777.\u003c/li\u003e\n\u003c/ol\u003e"},{"header":"Scheme","content":"\u003cp\u003eSchemes 1 and 2 is available in the Supplementary Files section.\u0026nbsp;\u003c/p\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":false,"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":"1,10-phenanthroline, dye sensitized solar cell, photovoltaic applications, organic dyes","lastPublishedDoi":"10.21203/rs.3.rs-8128370/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-8128370/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eIn this study, organic dyes (B1 and B3) with a D\u0026ndash;π\u0026ndash;A architecture were synthesized for use in dye-sensitized solar cells (DSSCs). The molecules were designed with triphenylamine as the electron donor, an imidazole bridge, and 1,10-phenanthroline as an anchoring unit to facilitate efficient electron transfer to the semiconductor (TiO₂) surface. The multi-anchor structure of B3 was intended to enhance power conversion efficiency (PCE) by enabling more efficient electron injection from the donor group to the semiconductor. Structural characterization of the dyes was performed using FT-IR, NMR, mass spectrometry, UV-Vis spectroscopy, and electrochemical measurements. Theoretical calculations were performed using the density functional theory (DFT) method with the 6-31G(d)/LANL2DZ basis set. Theoretical analysis revealed that lower band gap energy would facilitate electron transfer between the HOMO and LUMO levels, thus potentially increasing PCE values. The B3 compound exhibited a lower band gap energy compared to B1. The DSSC device incorporating the multi-anchor B3 dye achieved higher power conversion efficiency than the device containing the single-anchor B1 dye. Photovoltaic measurements showed that the DSSC device incorporating B3 achieved a PCE of 0.61%, whereas the device with B1 reached a PCE of 0.28%. The obtained results showed that B3 compound possesses promising structural properties for photovoltaic applications.\u003c/p\u003e","manuscriptTitle":"Theoretical Studies and Photovoltaic Performance of 1,10- Phenanthroline Derivative Compound as a Multiple Anchor Group","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-11-28 06:38:10","doi":"10.21203/rs.3.rs-8128370/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-12-24T16:36:19+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-12-24T01:38:04+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-11-28T06:08:58+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"24136331004162590209049644752540693230","date":"2025-11-28T01:34:16+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"316027033333761240367609884943370402652","date":"2025-11-24T05:50:24+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"236151949655873573371019969598757881184","date":"2025-11-24T05:37:28+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-11-24T05:32:58+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-11-18T10:42:35+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-11-18T09:53:27+00:00","index":"","fulltext":""},{"type":"submitted","content":"Chemical Papers","date":"2025-11-16T15:53:24+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":"205cee6b-cff6-4b3c-a7ed-b37fc0bcaf61","owner":[],"postedDate":"November 28th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2026-03-23T16:05:08+00:00","versionOfRecord":{"articleIdentity":"rs-8128370","link":"https://doi.org/10.1007/s11696-026-04746-0","journal":{"identity":"chemical-papers","isVorOnly":false,"title":"Chemical Papers"},"publishedOn":"2026-03-18 15:58:49","publishedOnDateReadable":"March 18th, 2026"},"versionCreatedAt":"2025-11-28 06:38:10","video":"","vorDoi":"10.1007/s11696-026-04746-0","vorDoiUrl":"https://doi.org/10.1007/s11696-026-04746-0","workflowStages":[]},"version":"v1","identity":"rs-8128370","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-8128370","identity":"rs-8128370","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}