Synthesis, structural diversity, and methanol vapor adsorption properties of three Hg(II) halide complexes derived from a helical Schiff base

Synthesis, structural diversity, and methanol vapor adsorption properties of three Hg(II) halide complexes derived from a helical Schiff base | 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 Synthesis, structural diversity, and methanol vapor adsorption properties of three Hg(II) halide complexes derived from a helical Schiff base Chao Huang, Tao Jiang, Ji-Hong Lu This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-5731921/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 21 Feb, 2025 Read the published version in Structural Chemistry → Version 1 posted 8 You are reading this latest preprint version Abstract The Schiff base condensation reaction between precursor diamine N , N' -bis(2-aminophenyl)-pyridine-2,6-dicarboxamide and 1,8-naphthyridine-2-carbaldehyde yielded a racemic compound ( L P / L M ), which was characterized by 1 H/ 13 C NMR, infrared spectroscopy, elemental analysis, and single crystal X-ray diffraction. Three complexes, [Hg 2 L I 4 ] ( 1 ), [Hg 2 L Br 4 ] ( 2 ), and [Hg 2 L 2 Cl 4 ]‧2H 2 O ( 3 ) with different coordination configurations were obtained from the reaction of this compound with HgX 2 (X = I − , Br − , and Cl − ), respectively, and their crystal structures and coordination geometries were determined via single crystal X-ray diffraction techniques. Both 1 and 2 exist as dinuclear complexes with a 1:2 molar ratio of L and Hg(II), while 3 exists as a 44-membered metallamacrocycle with a 1:1 molar ratio of L and Hg(II). The structural diversity of these three complexes indicates that the counter anions have significant effects on the structural topology. In addition, the solid-state luminescence and the gas adsorption of these complexes towards methanol vapor at room temperature were investigated. Schiff base Racemic ligand Hg(II) complex Crystal structure Methanol vapor adsorption Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Introduction In the past decades, an ever-increasing number of interesting supramolecular architectures have been reported, including metal-ligand assembly systems, supramolecular cage, noncovalent supramolecular self-assembly, etc [1 − 6]. In many of these metal-ligand assembly systems, the organic spacer ligands’ molecular geometry, length, and the supramolecular contacts (π···π stacking, hydrogen bonds, and other weak interactions) play critical roles in the construction of desirable coordination architectures [7 − 9]. By careful selection of metal ion ‘nodes’ and organic ‘linkers’ with clear coordination preferences, various coordination networks with specific topology have been successfully constructed [10 − 13]. On the other hand, transition metal coordination compounds, including Hg(II) complexes, play significant roles in supramolecular chemistry because of their interesting structural features and wide applications in different fields, such as catalyst, dye adsorption, gas storage, photoluminescence, electronic, and magnetic properties [14 − 18]. Hg(II), as an electron-withdrawing metal ion, can change and tune the luminescence properties of organic ligands, which is therefore widely used in the design of coordination supramolecular structures [19 − 21]. Furthermore, the flexible coordination number and versatile coordination behavior of Hg(II) ions enable the formation of different assemblies with different properties [22 − 24]. By regulating other additional conditions, such as the ligands, the counter anions, the reaction solvents, as well as the metal-to-ligand ratios, it is possible to obtain more coordination structures with desired properties [25 − 27]. Racemic ligands derived from pyridine-2,6-dicarboxamide (PDA) units belong to a kind of compounds with helical configuration, which have been reported in previous references [28 − 30]. In this contribution, by introducing 1,8-naphthyridine as a functional group with good coordination ability, we have designed and synthesized a new helical Schiff base compound containing both 1,8-naphthyridine and PDA units (Scheme 1 ). Three Hg(II) complexes were synthesized from this compound with HgX 2 (X = I − , Br − , and Cl − ), respectively (Scheme 2 ). From the different geometries of these complexes, it was clearly found that the racemic Schiff base compound presented different coordination modes in the coordination reaction with different Hg(II) ions. Moreover, the solid-state luminescence and the gas adsorption of these complexes towards methanol vapor were investigated as well. Experimental Materials and measurements The chemicals and solvents were commercially available and used as received. 1 H/ 13 C NMR spectra were recorded in CDCl 3 on a Bruker Avance III HD 400 Digital NMR spectrometer. Elemental analysis for C, H, and N was performed on a Vario EL III elemental analyzer. Infrared spectra (IR, 4000 − 400 cm − 1 ) of the solid samples were obtained on a Bruker FT-IR spectrophotometer using KBr discs. Single crystal X-ray diffraction data were collected on a Bruker D8 Venture diffractometer. The powder X-ray diffraction (PXRD) patterns were obtained on a Bruker D8 Advance diffractometer. The thermogravimetric analyses (TGA) were carried out on a Perkin-Elmer TGA7 analyzer in the range of 25 − 800°C. The solid-state luminescence emission spectra were recorded on an Agilent Cary Eclipse fluorescence spectrophotometry. The gas adsorption isotherms were recorded via a Micromeritics ASAP 2020 analyzer. Synthesis N , N′ -bis(2-aminophenyl)-pyridine-2,6-dicarboxamide (0.486 g, 1.4 mmol), synthesized by following the literature [ 31 ], was mixed with 1,8-naphthyridine-2-carbaldehyde (0.443 g, 2.8 mmol) in anhydrous ethanol (120 mL). The solution was stirred with refluxing for 12 h, then the resulting precipitate was filtered off and dried to give Schiff base ligand L . Yield: 0.554 g (63.1%). 1 H NMR (CDCl 3 , 400 MHz): δ 11.20 (s, 2H, CONH), 9.11 (d, 2H, J = 4.0 Hz, Py-H), 8.80 (d, 2H, J = 8.4 Hz, Py-H), 8.59 (s, 2H, CH = N), 8.53 (d, 2H, J = 8.0 Hz, Py-H), 8.29 (d, 2H, J = 8.0 Hz, Py-H), 8.21 (t, 1H, J = 8.0 Hz, Py-H), 7.85 (dd, 2H, J = 4.4, 2.0 Hz, Py-H), 7.44 (q, 2H, J = 4.0 Hz, Py-H), 7.30 (m, 4H, Ar-H), 6.87 (d, 2H, J = 4.0 Hz, Ar-H), 6.77 (t, 2H, J = 8.0 Hz, Ar-H). 13 C NMR (CDCl 3 , 100 MHz): δ 161.52, 159.89, 156.76, 155.80, 153.83, 149.31, 139.38, 137.57, 137.27, 137.02, 133.98, 128.57, 125.61, 124.37, 123.49, 122.81, 119.32, 118.66, 116.73. Anal. Calc. for C 37 H 25 N 9 O 2 (%): C 70.80, H 4.01, N 20.08; Found: C 70.90, H 3.93, N 19.97. IR (KBr, cm − 1 ): 3442 ( w ), 1679 ( s ), 1589 ( m ), 1519 ( s ), 1443 ( m ), 1311 ( w ), 1061 ( w ), 849 ( w ), 756 ( m ), 674 ( w ). [Hg 2 L I 4 ] ( 1 ). A methanolic solution (40 mL) of HgI 2 (45.4 mg, 0.10 mmol) was added slowly to a solution of L (31.4 mg, 0.05 mmol) in DMF (30 mL). The solution was stirred with refluxing for 20 min and then filtered off. The filtrate was left for slow evaporation, and yellow crystals suitable for X-ray analysis were obtained after 4 days. The crystals were filtered off, washed with methanol, and dried to give complex 1 . Yield: 41.6 mg (54.1%). Anal. Calc. for C 37 H 25 Hg 2 I 4 N 9 O 2 (%): C 28.92, H 1.64, N 8.20; Found: C 28.82, H 1.58, N 8.31. IR (KBr, cm − 1 ): 3445 ( m ), 1679 ( s ), 1588 ( w ), 1519 ( m ), 1442 ( w ), 1312 ( w ), 1121 ( m ), 853 ( w ), 756 ( m ), 621 ( w ). [Hg 2 L Br 4 ] ( 2 ). A methanolic solution (40 mL) of HgBr 2 (36.0 mg, 0.10 mmol) was added slowly to a solution of L (31.4 mg, 0.05 mmol) in DMF (30 mL). Then the same process was used as for 1 . Yield: 41.9 mg (62.2%). Anal. Calc. for C 37 H 25 Br 4 Hg 2 N 9 O 2 (%): C 32.96, H 1.87, N 9.35; Found: C 33.10, H 1.78, N 9.27. IR (KBr, cm − 1 ): 3452 ( w ), 3326 ( w ), 2981 ( w ), 1675 ( s ), 1592 ( m ), 1525 ( s ), 1443 ( m ), 1059 ( m ), 852 ( w ), 754 ( m ). [Hg 2 L 2 Cl 4 ]‧2H 2 O ( 3 ). A methanolic solution (40 mL) of HgCl 2 (27.1 mg, 0.10 mmol) was added slowly to a solution of L (62.7 mg, 0.10 mmol) in DMF (40 mL). Then the same process was used as for 1 . Yield: 52.2 mg (58.5%). Anal. Calc. for C 74 H 50 Cl 4 Hg 2 N 18 O 4 + 2H 2 O (%): C 48.45, H 2.97, N 13.74; Found: C 48.56, H 2.87, N 13.68. IR (KBr, cm − 1 ): 3499 ( w ), 1677 ( s ), 1594 ( m ), 1525 ( s ), 1445 ( m ), 1312 ( w ), 1198 ( w ), 1123 ( w ), 850 ( w ), 753 ( m ). X‑ray crystallography Single crystal X-ray diffraction analysis data for L and complexes 1 – 3 were collected on a Bruker D8 Venture diffractometer (Mo Kα radiation) at 293(2) K. The structures were solved using direct methods with the SHELXS-2014 program and refined by a full-matrix least-squares procedure with the SHELXL-2014 program [ 32 , 33 ]. All hydrogen atoms in the structures were produced theoretically on the parent atoms and refined with isotropic thermal displacement parameters. The lattice water molecules in the structures of L and complex 3 were highly disordered, which have been removed from the structural data by PLATON/SQUEEZE. Crystallographic data and structure refinement parameters are summarized in Table 1 . Selected bond lengths and angles are listed in Table S1 . Hydrogen bond distances and angles for the complexes are listed in Table S2. Table 1 Crystallographic data and structure refinement parameters for L and complexes 1 – 3 Compound L 1 2 3 Empirical formula C 37 H 25 N 9 O 2 C 37 H 25 Hg 2 I 4 N 9 O 2 C 37 H 25 Br 4 Hg 2 N 9 O 2 C 74 H 50 Cl 4 Hg 2 N 18 O 4 Formula weight 627.66 1536.44 1348.48 1748.91 Crystal system triclinic monoclinic triclinic triclinic Space group P ī C 2/ c P ī P ī a / (Å) 10.283(9) 18.103(3) 9.3964(11) 11.2682(15) b / (Å) 12.386(10) 15.001(3) 13.7363(18) 11.4285(14) c / (Å) 13.525(12) 15.809(2) 16.529(2) 14.6053(19) α / (°) 82.16(3) 90 102.748(4) 82.159(4) β / (°) 76.59(3) 101.874(6) 99.631(4) 85.269(4) γ / (°) 81.07(2) 90 104.978(4) 76.557(4) V / (Å 3 ) 1646(2) 4201.2(11) 1952.3(4) 1809.7(4) Z 2 4 2 1 D c / (g·cm − 3 ) 1.266 2.429 2.294 1.605 θ range / (°) 2.29 ~ 25.00 2.35 ~ 25.00 2.31 ~ 25.00 2.27 ~ 28.35 Absorption coefficient/ mm − 1 0.083 10.283 11.994 4.445 F (000) 652 2792 1252 831 Reflections collected 33698 50311 51169 43712 Independent reflections 5799 3691 6867 8994 Observed reflections ( I > 2 σ ( I )) 2571 2871 5198 5767 Number of parameters 433 245 487 460 Goodness-of-fit on F 2 0.961 1.048 1.053 1.022 Final R indices ( I > 2 σ ( I )) R 1 = 0.0844, wR 2 = 0.2202 R 1 = 0.0325, wR 2 = 0.0790 R 1 = 0.0353, wR 2 = 0.0798 R 1 = 0.0639, wR 2 = 0.1402 R indices (all data) R 1 = 0.1743, wR 2 = 0.2578 R 1 = 0.0471, wR 2 = 0.0843 R 1 = 0.0554, wR 2 = 0.0862 R 1 = 0.1135, wR 2 = 0.1642 Largest diff. Peak and hole (e Å −3 ) 0.207 and − 0.285 1.343 and − 1.380 1.060 and − 1.589 0.845 and − 1.598 Results and discussion Description of crystal structures X-ray quality single crystals of L were obtained from the solution of MeOH/DMF ( V / V = 3:1). The single crystals belong to a triclinic crystal system with P ī space group. The terminal fragments containing 1,8-naphthyridine units as two arms of L are crossed in the front of the central PDA unit (Fig. 1 a), leading to a racemic conformation with equal amounts of P - and M -helicity enantiomers, which is similar with our previous reports [ 28 , 30 , 34 ]. Each P -helicity enantiomer is found to be associated with adjacent M -helicity enantiomer through weak intermolecular interactions to form a 2D supramolecular structure (Fig. 1 b). Yellow crystals of complex 1 were obtained via slow solvent evaporation of L and HgI 2 in the solution of MeOH/DMF ( V / V = 4:3). The crystals crystallize in a monoclinic crystal system with C 2/ c space group, and the asymmetric unit is comprised of two HgI 2 and a ligand L (Fig. 2 a). Each central Hg(II) ion is four-coordinated with two I – anions and two nitrogen atoms (N1 and N2) from the 1,8-naphthyridine units, leading to a distorted tetrahedral configuration with τ 4 = 0.71 ( τ 4 = 0 for a square planar geometry configuration, and τ 4 = 1 for a perfect tetrahedral geometry configuration) [ 35 ]. The bond lengths of N–Hg and I–Hg vary from 2.512 to 2.759 Å, and the bond angles around the central Hg(II) ion are in the range of 51.22–147.56°, which are similar to other tetrahedral HgI 2 complexes [ 36 , 37 ]. In the packing structure, adjacent ligands of opposite helicity are linked through weak interactions to form a 3D structure (Fig. 2 b). When the counter anion was changed from I − to Br − , complex 2 was obtained with a different configuration from 1 . The complex crystallizes in a triclinic crystal system with P ī space group, and the asymmetric unit is comprised of two HgBr 2 and a ligand L . Each Hg(II) ion in 2 is four-coordinated with three Br − anions and a nitrogen atom in a distorted tetrahedral geometry ( τ 4 = 0.76 for Hg1 center and τ 4 = 0.71 for Hg2 center). Of the three Br − anions, one acts as a terminal ligand and the other two act as µ 2 -bridging ligands between two Hg(II) ions to establish a Hg–(Br) 2 –Hg quadrilateral (Fig. 3 a). The bond lengths of Hg1–N1 and Hg2–N9 are 2.282(5) and 2.324(5) Å, and the bond lengths of Hg–Br vary from 2.5251 to 2.9655 Å, which are consistent with previously reported complexes [ 38 , 39 ]. The bond angles around Hg1 and Hg2 centers vary from 88.05 to 134.40°, and the Hg···Hg distance bridged by ligand L is 3.882 Å. Similarly, adjacent ligands of opposite helicity form a 3D supramolecular structure through weak intermolecular hydrogen bonds (Fig. 3 b). Yellow crystals of complex 3 were obtained via slow solvent evaporation of HgCl 2 and ligand L in the solution of MeOH/DMF ( V / V = 1:1). The complex exists as a binuclear 44-membered metallamacrocycle in a twisted figure-eight conformation (Fig. 4 a). Each central Hg(II) ion is four-coordinated with two Cl – anions and two nitrogen atoms from adjacent 1,8-naphthyridine units in a tetrahedral configuration with τ 4 = 0.60. The bond lengths of Hg–Cl and Hg–N are in the range of 2.379 and 2.650 Å, and the bond angles around the Hg(II) ion vary from 90.33 to 152.04°, which are similar to the related complexes [ 40 , 41 ]. Each macrocycle exists as a mesomer of one M -helicity enantiomer and one P -helicity enantiomer, which is further connected to adjacent macrocycle through weak intermolecular interactions to form 1D channels in the 3D network (Fig. 4 b). In this work, three HgX 2 (X = I − , Br − , and Cl − ) salts were used to synthesize complexes 1 − 3 under similar conditions. It is observed that the Hg(II) ions exhibit different coordination environments in complexes 1 − 3 due to the different anions used (Fig. 5 ). In complex 1 , each Hg(II) ion coordinates to both of the two nitrogen atoms in the 1,8-naphthyridine units. In complex 2 , each Hg(II) ion only coordinates to the nitrogen atoms at 8-position of the 1,8-naphthyridine units. Upon replacement of I − or Br − with Cl − , a 44-membered metallamacrocycle was obtained in complex 3 , in which one of the Hg(II) ions coordinates to the nitrogen atom at 1-position of the 1,8-naphthyridine units, while the other one coordinates to the nitrogen atom at 8-position of the 1,8-naphthyridine units. All of these Hg(II) ions in the three complexes are four-coordinated in a distorted tetrahedral configuration. The structural differences of complexes 1 − 3 may be attributed to the different ionic radius of the anions. In addition, by comparing the coordination configurations of complexes 1 – 3 , it is noteworthy that complexes 1 and 2 are racemic, while complex 3 is mesomeric, revealing their structural differences in chiral self-assembly. PXRD and TGA analysis The PXRD patterns of the three synthesized complexes are in good agreement with the simulated patterns, showing good phase purities of complexes 1 – 3 (Fig. S7). The thermal stabilities of complexes 1 – 3 were recorded in the range of 25 − 800 ℃ (Fig. 6 ). Complexes 1 and 2 are stable below 220 ℃, then they begin to decompose and loss weight obviously in the range of 220 − 400 ℃. Complex 3 exhibits a slight weight loss (2.0%) from 25 to 70 ℃, which is relevant to the loss of two lattice water molecules (calculated 2.0%) in the crystals. After further heating, a weight loss of 21.1% can be observed in the range of 250 − 500 ℃ due to decomposition of the organic framework. The results show that all the complexes have good thermal stability. Solid-state luminescence The solid-state luminescence of complexes 1 – 3 and L were studied at room temperature (Fig. 7 ). Upon excitation at λ = 380 nm, the maximum luminescence emission of L can be observed at 500 nm, which is due to the π–π* and n–π* transition [ 42 , 43 ]. Complex 1 shows a maximum luminescence emission peak at 516 nm (λ ex = 390 nm). When excited at the same wavelength, complexes 2 and 3 show emission maxima at 515 and 518 nm, respectively. These slight red shifts compared with L should be ascribe to the coordination of L to Hg(II) ions. In addition, the fluorescence intensity of these three complexes is much lower in comparison with L , which means that the complexation of ligand L with Hg(II) ions has a negative effect on the fluorescence intensity. Methanol vapor adsorption for the complexes Considering the abundant hydrogen bonding sites in the three complexes, we studied the gas adsorption of the three complexes towards methanol vapor at room temperature. The synthesized powder samples were activated in a dynamic vacuum at 373 K for 5 hours to remove the solvent molecules, then the adsorption isotherms towards methanol vapor were recorded at room temperature (298 K). As shown in Fig. 8 , the largest quantity adsorbed of the three complexes towards methanol vapor at P / P 0 = 0.99 increases as follows: 1 (25.2 cm 3 /g STP) < 2 (28.8 cm 3 /g STP ) < 3 (65.5 cm 3 /g STP). Base on the good adsorption performance, it is inferred that the methanol molecules mainly bind to the ligands in the complexes through hydrogen bonds [ 29 , 44 , 45 ]. Furthermore, the experimental results show that with the increase of the cavity ( 1 < 2 < 3 ) in the assembly structures of the complexes, more methanol molecules form hydrogen bonds with the ligand, which leads to the increase of the adsorption of methanol vapor. Conclusions In summary, a helical Schiff base compound ( L ) containing both 1,8-naphthyridine and PDA units was synthesized and characterized. The crystal structure shows a racemic conformation with equal amounts of P - and M -helicity enantiomers in the compound. Furthermore, under similar solvent evaporation conditions, the assembly of this ligand with Hg(II) halide (HgI 2 , HgBr 2 , and HgCl 2 ) resulted in three complexes with different coordination configuration, which may be attributed to the different ionic radius of the halide anions. In addition, the gas adsorption of the synthesized complexes towards methanol vapor was investigated. The results showed that complex 3 exhibited an obviously better adsorption capacity towards methanol vapor over complexes 1 and 2 , which can be attributed to the larger cavity in the assembly structure of complex 3 . Declarations Competing interests The authors declare no competing interests. Funding This work was financially supported by the National Natural Science Foundation of China (22461009), the Guizhou Provincial Science and Technology Projects (ZK[2024]080), and the Guizhou Provincial Key Laboratory Platform Project (ZSYS[2025]008). Author Contribution C. Huang synthesized L and the three complexes and determined the crystal structures of these compounds. T. Jiang tested the solid-state luminescence and vapor adsorption properties of the complexes. J.-H. Lu analyzed the properties of the complexes and wrote the main manuscript text. All authors reviewed the manuscript. Data Availability Data is provided within the manuscript or supplementary information files. References Gu Y, Wu Y, Li L, Chen W, Li F, Kitagawa S (2017) Controllable Modular Growth of Hierarchical MOF-on-MOF Architectures. 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Dalton Trans 46:3579–3587. https://doi.org/10.1039/C7DT00050B Huang C, Yang J, Chen JL, Chen DM, Zhu BX (2018) Synthesis and crystal structures of metallomacrocyclic and helical Hg(II) complexes with two bis(pyridylurea) ligands. Inorg Chim Acta 483:252–257. https://doi.org/10.1016/j.ica.2018.08.020 Khavasi HR, Fard MA (2010) π-π Interactions Affect Coordination Geometries. Cryst Growth Des 10(4):1892–1896. https://doi.org/10.1021/cg100265d Yu HH, He SX, Lu JH, Huang C, Chen DM, Zhu BX (2023) Synthesis, crystal structures, photophysical and antibacterial properties of Ag(I) and Zn(II) coordination polymers based on a flexible bisacylhydrazone ligand. Inorg Chim Acta 557:121713. https://doi.org/10.1016/j.ica.2023.121713 Jiang T, Tian LC, Mo XJ, Chen DM, Huang C, Zhu BX, Zhu C (2022) Synthesis, structural diversity, DFT and luminescence properties of Ni(II), Zn(II) and Cd(II) complexes derived from a 2,2’-bipyridyl hydrazone Schiff base. Polyhedron 221:115861. https://doi.org/10.1016/j.poly.2022.115861 Huang X, Yan SY, Chen YM, Zhang DS, Huang C, Zhu BX, Lu JH (2023) Synthesis, structures, and gas adsorption properties of Hg(II) and Cd(II) complexes constructed from two acylhydrazone ligands with multiple coordination sites. Inorg Chim Acta 555:121588. https://doi.org/10.1016/j.ica.2023.121588 Liu YJ, Chen YT, Chen MZ, Mo XJ, Huang C, Chen DM, Zhu BX (2020) Self-discriminating and counteranion-controlled self-assembly: Two heterochiral Cd(II) coordination polymers based on a racemic bis(pyridyl) ligand. Inorg Chim Acta 510:119702. https://doi.org/10.1016/j.ica.2020.119702 Scheme Schemes 1 and 2 are available in the Supplementary Files section Additional Declarations No competing interests reported. Supplementary Files Supplementarymaterial.docx S1.png Scheme 1 Synthetic route of racemic Schiff base ligand L. S2.png Scheme 2 Synthetic process used to prepare the three Hg(II) halide complexes. Cite Share Download PDF Status: Published Journal Publication published 21 Feb, 2025 Read the published version in Structural Chemistry → Version 1 posted Editorial decision: Revision requested 24 Jan, 2025 Reviews received at journal 17 Jan, 2025 Reviewers agreed at journal 06 Jan, 2025 Reviewers agreed at journal 02 Jan, 2025 Reviewers invited by journal 30 Dec, 2024 Editor assigned by journal 30 Dec, 2024 Submission checks completed at journal 30 Dec, 2024 First submitted to journal 29 Dec, 2024 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-5731921","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":396193193,"identity":"f6d11505-eff1-4a3e-a730-640db62feb73","order_by":0,"name":"Chao Huang","email":"","orcid":"","institution":"Guizhou University","correspondingAuthor":false,"prefix":"","firstName":"Chao","middleName":"","lastName":"Huang","suffix":""},{"id":396193194,"identity":"e41b1107-f072-49e5-a066-0922e473333e","order_by":1,"name":"Tao Jiang","email":"","orcid":"","institution":"Guizhou University","correspondingAuthor":false,"prefix":"","firstName":"Tao","middleName":"","lastName":"Jiang","suffix":""},{"id":396193195,"identity":"fc10decf-419a-4dda-ae7f-6acf1e77e68a","order_by":2,"name":"Ji-Hong Lu","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAsklEQVRIiWNgGAWjYBACPgaGNBAtx8befoA4LWxQLcZ8PGcSiNbCBqIT50k4GBCpRSLh2cMvfw6nt0kwJDD8qNhGlJZ0Yxmew7lt0o0HGHvO3CZKS5q0hARQi8yBBGbGNqK1GBxOBzIMiNci+SHhcAIJWngepEkzHEg3bAMG8kGi/MLPnpMm+eOPtbx8e/vBBz8qiNDCwMCTwMwDZR4gRj0QsB9g/EGk0lEwCkbBKBihAAC12zbVohWQQQAAAABJRU5ErkJggg==","orcid":"","institution":"Guizhou University","correspondingAuthor":true,"prefix":"","firstName":"Ji-Hong","middleName":"","lastName":"Lu","suffix":""}],"badges":[],"createdAt":"2024-12-30 01:38:04","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-5731921/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-5731921/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1007/s11224-025-02473-y","type":"published","date":"2025-02-21T15:57:26+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":72754548,"identity":"bc5b4ea6-6068-43f3-b944-60a4a308a430","added_by":"auto","created_at":"2025-01-01 16:44:28","extension":"jpg","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":147182,"visible":true,"origin":"","legend":"\u003cp\u003e(a) Crystal structure of \u003cstrong\u003eL\u003c/strong\u003e. (b) View of 2D packing structure through intermolecular interactions along the \u003cem\u003ebc\u003c/em\u003e plane.\u003c/p\u003e","description":"","filename":"1.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/41d22334a77fda0e66469710.jpg"},{"id":72754764,"identity":"7a60d5d2-f199-4165-a14a-e35728092a33","added_by":"auto","created_at":"2025-01-01 16:52:28","extension":"jpg","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":160549,"visible":true,"origin":"","legend":"\u003cp\u003e(a) Crystal structure and coordination geometry of \u003cstrong\u003e1\u003c/strong\u003e. (b) View of 3D packing structure through weak interactions along the \u003cem\u003eab\u003c/em\u003e plane.\u003c/p\u003e","description":"","filename":"Picture2.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/185c7bf4c4b3ccd3397c9627.jpg"},{"id":72753992,"identity":"a1ef9c33-ed3d-40a5-82c7-5292e76d90a4","added_by":"auto","created_at":"2025-01-01 16:36:28","extension":"jpg","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":146336,"visible":true,"origin":"","legend":"\u003cp\u003e(a) Crystal structure and coordination geometry of \u003cstrong\u003e2\u003c/strong\u003e. (b) View of 3D packing structure through weak intermolecular hydrogen bonds.\u003c/p\u003e","description":"","filename":"Picture3.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/eb8ab3c271770d46d9ab3a10.jpg"},{"id":72754005,"identity":"d2101235-242b-4d3c-9c61-153e1887babe","added_by":"auto","created_at":"2025-01-01 16:36:28","extension":"jpg","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":168223,"visible":true,"origin":"","legend":"\u003cp\u003e(a) Crystal structure and coordination geometry of \u003cstrong\u003e3\u003c/strong\u003e. (b) The 1D channels formed in the 3D network of \u003cstrong\u003e3\u003c/strong\u003e.\u003c/p\u003e","description":"","filename":"Picture4.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/d3d59c532f8a0162b7d73b04.jpg"},{"id":72754013,"identity":"70275754-4902-447a-9820-11067ef383ac","added_by":"auto","created_at":"2025-01-01 16:36:28","extension":"jpg","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":84392,"visible":true,"origin":"","legend":"\u003cp\u003eThe coordination geometries of Hg(II) ions in complexes \u003cstrong\u003e1\u003c/strong\u003e–\u003cstrong\u003e3\u003c/strong\u003e.\u003c/p\u003e","description":"","filename":"Picture5.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/a1d8cc27505f56c6099e6ebb.jpg"},{"id":72754004,"identity":"0f2a9253-b6cb-4adb-8e20-408a10d8e695","added_by":"auto","created_at":"2025-01-01 16:36:28","extension":"jpg","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":43565,"visible":true,"origin":"","legend":"\u003cp\u003eTGA curves for complexes \u003cstrong\u003e1\u003c/strong\u003e–\u003cstrong\u003e3\u003c/strong\u003e.\u003c/p\u003e","description":"","filename":"Picture6.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/bd02dd1a8b4f3769308844c9.jpg"},{"id":72754009,"identity":"2dcefc18-8773-4740-958f-5aeb0b571117","added_by":"auto","created_at":"2025-01-01 16:36:28","extension":"jpg","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":52433,"visible":true,"origin":"","legend":"\u003cp\u003eSolid-state luminescence emission spectra of ligand \u003cstrong\u003eL\u003c/strong\u003e and complexes \u003cstrong\u003e1\u003c/strong\u003e–\u003cstrong\u003e3\u003c/strong\u003e.\u003c/p\u003e","description":"","filename":"Picture7.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/87cae7ceb2e79f067640ad23.jpg"},{"id":72753993,"identity":"3981881a-ad31-4689-a1ae-d6e09968a486","added_by":"auto","created_at":"2025-01-01 16:36:28","extension":"jpg","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":50956,"visible":true,"origin":"","legend":"\u003cp\u003eMethanol vapor adsorption isotherms for complexes\u003cstrong\u003e 1\u003c/strong\u003e–\u003cstrong\u003e3\u003c/strong\u003eat 298 K.\u003c/p\u003e","description":"","filename":"Picture8.jpg","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/bafaa6323940978ee1809bdd.jpg"},{"id":77052745,"identity":"99ca8907-fea7-443a-b22a-9bead61a7383","added_by":"auto","created_at":"2025-02-24 16:24:19","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":1658883,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/469be535-d1a0-4ff4-a715-cdae6ab61a0e.pdf"},{"id":72754765,"identity":"7ae6dfd0-7f39-4812-a0e5-69275b17d25d","added_by":"auto","created_at":"2025-01-01 16:52:28","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":259842,"visible":true,"origin":"","legend":"","description":"","filename":"Supplementarymaterial.docx","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/09b11a43a454479df75bce1d.docx"},{"id":72753988,"identity":"49272fd8-82c2-4dd2-8510-0f04b8396713","added_by":"auto","created_at":"2025-01-01 16:36:28","extension":"png","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":20402,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 1 \u003c/strong\u003eSynthetic route of racemic Schiff base ligand \u003cstrong\u003eL\u003c/strong\u003e.\u003c/p\u003e","description":"","filename":"S1.png","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/38ec50d122524e37981cb7d9.png"},{"id":72754550,"identity":"cff37b73-cac1-45d2-8a2d-6a9915eea718","added_by":"auto","created_at":"2025-01-01 16:44:28","extension":"png","order_by":3,"title":"","display":"","copyAsset":false,"role":"supplement","size":72056,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 2\u003c/strong\u003e Synthetic process used to prepare the three Hg(II) halide complexes.\u003c/p\u003e","description":"","filename":"S2.png","url":"https://assets-eu.researchsquare.com/files/rs-5731921/v1/5d33ae999a1375567cd14697.png"}],"financialInterests":"No competing interests reported.","formattedTitle":"Synthesis, structural diversity, and methanol vapor adsorption properties of three Hg(II) halide complexes derived from a helical Schiff base","fulltext":[{"header":"Introduction","content":"\u003cp\u003eIn the past decades, an ever-increasing number of interesting supramolecular architectures have been reported, including metal-ligand assembly systems, supramolecular cage, noncovalent supramolecular self-assembly, etc [1\u0026thinsp;\u0026minus;\u0026thinsp;6]. In many of these metal-ligand assembly systems, the organic spacer ligands\u0026rsquo; molecular geometry, length, and the supramolecular contacts (π\u0026middot;\u0026middot;\u0026middot;π stacking, hydrogen bonds, and other weak interactions) play critical roles in the construction of desirable coordination architectures [7\u0026thinsp;\u0026minus;\u0026thinsp;9]. By careful selection of metal ion \u0026lsquo;nodes\u0026rsquo; and organic \u0026lsquo;linkers\u0026rsquo; with clear coordination preferences, various coordination networks with specific topology have been successfully constructed [10\u0026thinsp;\u0026minus;\u0026thinsp;13].\u003c/p\u003e \u003cp\u003eOn the other hand, transition metal coordination compounds, including Hg(II) complexes, play significant roles in supramolecular chemistry because of their interesting structural features and wide applications in different fields, such as catalyst, dye adsorption, gas storage, photoluminescence, electronic, and magnetic properties [14\u0026thinsp;\u0026minus;\u0026thinsp;18]. Hg(II), as an electron-withdrawing metal ion, can change and tune the luminescence properties of organic ligands, which is therefore widely used in the design of coordination supramolecular structures [19\u0026thinsp;\u0026minus;\u0026thinsp;21]. Furthermore, the flexible coordination number and versatile coordination behavior of Hg(II) ions enable the formation of different assemblies with different properties [22\u0026thinsp;\u0026minus;\u0026thinsp;24]. By regulating other additional conditions, such as the ligands, the counter anions, the reaction solvents, as well as the metal-to-ligand ratios, it is possible to obtain more coordination structures with desired properties [25\u0026thinsp;\u0026minus;\u0026thinsp;27].\u003c/p\u003e \u003cp\u003eRacemic ligands derived from pyridine-2,6-dicarboxamide (PDA) units belong to a kind of compounds with helical configuration, which have been reported in previous references [28\u0026thinsp;\u0026minus;\u0026thinsp;30]. In this contribution, by introducing 1,8-naphthyridine as a functional group with good coordination ability, we have designed and synthesized a new helical Schiff base compound containing both 1,8-naphthyridine and PDA units (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e). Three Hg(II) complexes were synthesized from this compound with HgX\u003csub\u003e2\u003c/sub\u003e (X\u0026thinsp;=\u0026thinsp;I\u003csup\u003e\u0026minus;\u003c/sup\u003e, Br\u003csup\u003e\u0026minus;\u003c/sup\u003e, and Cl\u003csup\u003e\u0026minus;\u003c/sup\u003e), respectively (Scheme \u003cspan refid=\"Sch2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). From the different geometries of these complexes, it was clearly found that the racemic Schiff base compound presented different coordination modes in the coordination reaction with different Hg(II) ions. Moreover, the solid-state luminescence and the gas adsorption of these complexes towards methanol vapor were investigated as well.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e"},{"header":"Experimental","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003eMaterials and measurements\u003c/h2\u003e \u003cp\u003eThe chemicals and solvents were commercially available and used as received. \u003csup\u003e1\u003c/sup\u003eH/\u003csup\u003e13\u003c/sup\u003eC NMR spectra were recorded in CDCl\u003csub\u003e3\u003c/sub\u003e on a Bruker Avance III HD 400 Digital NMR spectrometer. Elemental analysis for C, H, and N was performed on a Vario EL III elemental analyzer. Infrared spectra (IR, 4000\u0026thinsp;\u0026minus;\u0026thinsp;400 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) of the solid samples were obtained on a Bruker FT-IR spectrophotometer using KBr discs. Single crystal X-ray diffraction data were collected on a Bruker D8 Venture diffractometer. The powder X-ray diffraction (PXRD) patterns were obtained on a Bruker D8 Advance diffractometer. The thermogravimetric analyses (TGA) were carried out on a Perkin-Elmer TGA7 analyzer in the range of 25\u0026thinsp;\u0026minus;\u0026thinsp;800\u0026deg;C. The solid-state luminescence emission spectra were recorded on an Agilent Cary Eclipse fluorescence spectrophotometry. The gas adsorption isotherms were recorded via a Micromeritics ASAP 2020 analyzer.\u003c/p\u003e \u003c/div\u003e\n\u003ch3\u003eSynthesis\u003c/h3\u003e\n\u003cp\u003e \u003cem\u003eN\u003c/em\u003e,\u003cem\u003eN\u0026prime;\u003c/em\u003e-bis(2-aminophenyl)-pyridine-2,6-dicarboxamide (0.486 g, 1.4 mmol), synthesized by following the literature [\u003cspan citationid=\"CR31\" class=\"CitationRef\"\u003e31\u003c/span\u003e], was mixed with 1,8-naphthyridine-2-carbaldehyde (0.443 g, 2.8 mmol) in anhydrous ethanol (120 mL). The solution was stirred with refluxing for 12 h, then the resulting precipitate was filtered off and dried to give Schiff base ligand \u003cb\u003eL\u003c/b\u003e. Yield: 0.554 g (63.1%). \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz): \u003cem\u003eδ\u003c/em\u003e 11.20 (s, 2H, CONH), 9.11 (d, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;4.0 Hz, Py-H), 8.80 (d, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.4 Hz, Py-H), 8.59 (s, 2H, CH\u0026thinsp;=\u0026thinsp;N), 8.53 (d, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, Py-H), 8.29 (d, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, Py-H), 8.21 (t, 1H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, Py-H), 7.85 (dd, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;4.4, 2.0 Hz, Py-H), 7.44 (q, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;4.0 Hz, Py-H), 7.30 (m, 4H, Ar-H), 6.87 (d, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;4.0 Hz, Ar-H), 6.77 (t, 2H, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, Ar-H). \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz): \u003cem\u003eδ\u003c/em\u003e 161.52, 159.89, 156.76, 155.80, 153.83, 149.31, 139.38, 137.57, 137.27, 137.02, 133.98, 128.57, 125.61, 124.37, 123.49, 122.81, 119.32, 118.66, 116.73. Anal. Calc. for C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e25\u003c/sub\u003eN\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e (%): C 70.80, H 4.01, N 20.08; Found: C 70.90, H 3.93, N 19.97. IR (KBr, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 3442 (\u003cem\u003ew\u003c/em\u003e), 1679 (\u003cem\u003es\u003c/em\u003e), 1589 (\u003cem\u003em\u003c/em\u003e), 1519 (\u003cem\u003es\u003c/em\u003e), 1443 (\u003cem\u003em\u003c/em\u003e), 1311 (\u003cem\u003ew\u003c/em\u003e), 1061 (\u003cem\u003ew\u003c/em\u003e), 849 (\u003cem\u003ew\u003c/em\u003e), 756 (\u003cem\u003em\u003c/em\u003e), 674 (\u003cem\u003ew\u003c/em\u003e).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e[Hg\u003csub\u003e2\u003c/sub\u003e\u003cb\u003eL\u003c/b\u003eI\u003csub\u003e4\u003c/sub\u003e] (\u003cb\u003e1\u003c/b\u003e). A methanolic solution (40 mL) of HgI\u003csub\u003e2\u003c/sub\u003e (45.4 mg, 0.10 mmol) was added slowly to a solution of \u003cb\u003eL\u003c/b\u003e (31.4 mg, 0.05 mmol) in DMF (30 mL). The solution was stirred with refluxing for 20 min and then filtered off. The filtrate was left for slow evaporation, and yellow crystals suitable for X-ray analysis were obtained after 4 days. The crystals were filtered off, washed with methanol, and dried to give complex \u003cb\u003e1\u003c/b\u003e. Yield: 41.6 mg (54.1%). Anal. Calc. for C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e25\u003c/sub\u003eHg\u003csub\u003e2\u003c/sub\u003eI\u003csub\u003e4\u003c/sub\u003eN\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e (%): C 28.92, H 1.64, N 8.20; Found: C 28.82, H 1.58, N 8.31. IR (KBr, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 3445 (\u003cem\u003em\u003c/em\u003e), 1679 (\u003cem\u003es\u003c/em\u003e), 1588 (\u003cem\u003ew\u003c/em\u003e), 1519 (\u003cem\u003em\u003c/em\u003e), 1442 (\u003cem\u003ew\u003c/em\u003e), 1312 (\u003cem\u003ew\u003c/em\u003e), 1121 (\u003cem\u003em\u003c/em\u003e), 853 (\u003cem\u003ew\u003c/em\u003e), 756 (\u003cem\u003em\u003c/em\u003e), 621 (\u003cem\u003ew\u003c/em\u003e).\u003c/p\u003e \u003cp\u003e[Hg\u003csub\u003e2\u003c/sub\u003e\u003cb\u003eL\u003c/b\u003eBr\u003csub\u003e4\u003c/sub\u003e] (\u003cb\u003e2\u003c/b\u003e). A methanolic solution (40 mL) of HgBr\u003csub\u003e2\u003c/sub\u003e (36.0 mg, 0.10 mmol) was added slowly to a solution of \u003cb\u003eL\u003c/b\u003e (31.4 mg, 0.05 mmol) in DMF (30 mL). Then the same process was used as for \u003cb\u003e1\u003c/b\u003e. Yield: 41.9 mg (62.2%). Anal. Calc. for C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e25\u003c/sub\u003eBr\u003csub\u003e4\u003c/sub\u003eHg\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e (%): C 32.96, H 1.87, N 9.35; Found: C 33.10, H 1.78, N 9.27. IR (KBr, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 3452 (\u003cem\u003ew\u003c/em\u003e), 3326 (\u003cem\u003ew\u003c/em\u003e), 2981 (\u003cem\u003ew\u003c/em\u003e), 1675 (\u003cem\u003es\u003c/em\u003e), 1592 (\u003cem\u003em\u003c/em\u003e), 1525 (\u003cem\u003es\u003c/em\u003e), 1443 (\u003cem\u003em\u003c/em\u003e), 1059 (\u003cem\u003em\u003c/em\u003e), 852 (\u003cem\u003ew\u003c/em\u003e), 754 (\u003cem\u003em\u003c/em\u003e).\u003c/p\u003e \u003cp\u003e[Hg\u003csub\u003e2\u003c/sub\u003e\u003cb\u003eL\u003c/b\u003e\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e4\u003c/sub\u003e]‧2H\u003csub\u003e2\u003c/sub\u003eO (\u003cb\u003e3\u003c/b\u003e). A methanolic solution (40 mL) of HgCl\u003csub\u003e2\u003c/sub\u003e (27.1 mg, 0.10 mmol) was added slowly to a solution of \u003cb\u003eL\u003c/b\u003e (62.7 mg, 0.10 mmol) in DMF (40 mL). Then the same process was used as for \u003cb\u003e1\u003c/b\u003e. Yield: 52.2 mg (58.5%). Anal. Calc. for C\u003csub\u003e74\u003c/sub\u003eH\u003csub\u003e50\u003c/sub\u003eCl\u003csub\u003e4\u003c/sub\u003eHg\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u0026thinsp;+\u0026thinsp;2H\u003csub\u003e2\u003c/sub\u003eO (%): C 48.45, H 2.97, N 13.74; Found: C 48.56, H 2.87, N 13.68. IR (KBr, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 3499 (\u003cem\u003ew\u003c/em\u003e), 1677 (\u003cem\u003es\u003c/em\u003e), 1594 (\u003cem\u003em\u003c/em\u003e), 1525 (\u003cem\u003es\u003c/em\u003e), 1445 (\u003cem\u003em\u003c/em\u003e), 1312 (\u003cem\u003ew\u003c/em\u003e), 1198 (\u003cem\u003ew\u003c/em\u003e), 1123 (\u003cem\u003ew\u003c/em\u003e), 850 (\u003cem\u003ew\u003c/em\u003e), 753 (\u003cem\u003em\u003c/em\u003e).\u003c/p\u003e\n\u003ch3\u003eX‑ray crystallography\u003c/h3\u003e\n\u003cp\u003eSingle crystal X-ray diffraction analysis data for \u003cb\u003eL\u003c/b\u003e and complexes \u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e3\u003c/b\u003e were collected on a Bruker D8 Venture diffractometer (Mo Kα radiation) at 293(2) K. The structures were solved using direct methods with the SHELXS-2014 program and refined by a full-matrix least-squares procedure with the SHELXL-2014 program [\u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e32\u003c/span\u003e, \u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e]. All hydrogen atoms in the structures were produced theoretically on the parent atoms and refined with isotropic thermal displacement parameters. The lattice water molecules in the structures of \u003cb\u003eL\u003c/b\u003e and complex \u003cb\u003e3\u003c/b\u003e were highly disordered, which have been removed from the structural data by PLATON/SQUEEZE. Crystallographic data and structure refinement parameters are summarized in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e. Selected bond lengths and angles are listed in Table \u003cspan refid=\"MOESM1\" class=\"InternalRef\"\u003eS1\u003c/span\u003e. Hydrogen bond distances and angles for the complexes are listed in Table S2.\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\u003eCrystallographic data and structure refinement parameters for \u003cb\u003eL\u003c/b\u003e and complexes \u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e3\u003c/b\u003e\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=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCompound\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eL\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eEmpirical formula\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e25\u003c/sub\u003eN\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e25\u003c/sub\u003eHg\u003csub\u003e2\u003c/sub\u003eI\u003csub\u003e4\u003c/sub\u003eN\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e25\u003c/sub\u003eBr\u003csub\u003e4\u003c/sub\u003eHg\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e74\u003c/sub\u003eH\u003csub\u003e50\u003c/sub\u003eCl\u003csub\u003e4\u003c/sub\u003eHg\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eFormula weight\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e627.66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1536.44\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1348.48\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1748.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCrystal system\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003etriclinic\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003emonoclinic\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003etriclinic\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003etriclinic\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eSpace group\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cem\u003eP\u003c/em\u003eī\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003eC\u003c/em\u003e2/\u003cem\u003ec\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e\u003cem\u003eP\u003c/em\u003eī\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cem\u003eP\u003c/em\u003eī\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003ea\u003c/em\u003e / (\u0026Aring;)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e10.283(9)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e18.103(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e9.3964(11)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e11.2682(15)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eb\u003c/em\u003e / (\u0026Aring;)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e12.386(10)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e15.001(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e13.7363(18)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e11.4285(14)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003ec\u003c/em\u003e / (\u0026Aring;)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e13.525(12)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e15.809(2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e16.529(2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e14.6053(19)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eα\u003c/em\u003e / (\u0026deg;)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e82.16(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e90\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e102.748(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e82.159(4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eβ\u003c/em\u003e / (\u0026deg;)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e76.59(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e101.874(6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e99.631(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e85.269(4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eγ\u003c/em\u003e / (\u0026deg;)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e81.07(2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e90\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e104.978(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e76.557(4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eV\u003c/em\u003e / (\u0026Aring;\u003csup\u003e3\u003c/sup\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1646(2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4201.2(11)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1952.3(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1809.7(4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eZ\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eD\u003c/em\u003e\u003csub\u003ec\u003c/sub\u003e / (g\u0026middot;cm\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1.266\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2.429\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e2.294\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.605\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eθ\u003c/em\u003e range / (\u0026deg;)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2.29\u0026thinsp;~\u0026thinsp;25.00\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2.35\u0026thinsp;~\u0026thinsp;25.00\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e2.31\u0026thinsp;~\u0026thinsp;25.00\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e2.27\u0026thinsp;~\u0026thinsp;28.35\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAbsorption coefficient/ mm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.083\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10.283\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e11.994\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e4.445\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eF\u003c/em\u003e(000)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e652\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2792\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1252\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e831\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eReflections collected\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e33698\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e50311\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e51169\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e43712\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eIndependent reflections\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5799\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e3691\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e6867\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e8994\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eObserved reflections (\u003cem\u003eI\u003c/em\u003e\u0026thinsp;\u0026gt;\u0026thinsp;2\u003cem\u003eσ\u003c/em\u003e(\u003cem\u003eI\u003c/em\u003e))\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2571\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2871\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e5198\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e5767\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eNumber of parameters\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e433\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e245\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e487\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e460\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eGoodness-of-fit on \u003cem\u003eF\u003c/em\u003e \u003csup\u003e2\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.961\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.048\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.053\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.022\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eFinal \u003cem\u003eR\u003c/em\u003e indices (\u003cem\u003eI\u003c/em\u003e\u0026thinsp;\u0026gt;\u0026thinsp;2\u003cem\u003eσ\u003c/em\u003e(\u003cem\u003eI\u003c/em\u003e))\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0844, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.2202\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0325, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0790\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0353, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0798\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0639, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.1402\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e indices (all data)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.1743, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.2578\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0471, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0843\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0554, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.0862\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cem\u003eR\u003c/em\u003e\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.1135, \u003cem\u003ewR\u003c/em\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.1642\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eLargest diff. Peak and hole (e \u0026Aring;\u003csup\u003e\u0026minus;3\u003c/sup\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.207 and \u0026minus;\u0026thinsp;0.285\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.343 and \u0026minus;\u0026thinsp;1.380\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.060 and \u0026minus;\u0026thinsp;1.589\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.845 and \u0026minus;\u0026thinsp;1.598\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e"},{"header":"Results and discussion","content":"\u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003eDescription of crystal structures\u003c/h2\u003e \u003cp\u003eX-ray quality single crystals of \u003cb\u003eL\u003c/b\u003e were obtained from the solution of MeOH/DMF (\u003cem\u003eV\u003c/em\u003e/\u003cem\u003eV\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3:1). The single crystals belong to a triclinic crystal system with \u003cem\u003eP\u003c/em\u003eī space group. The terminal fragments containing 1,8-naphthyridine units as two arms of \u003cb\u003eL\u003c/b\u003e are crossed in the front of the central PDA unit (Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003ea), leading to a racemic conformation with equal amounts of \u003cem\u003eP\u003c/em\u003e- and \u003cem\u003eM\u003c/em\u003e-helicity enantiomers, which is similar with our previous reports [\u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e28\u003c/span\u003e, \u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e30\u003c/span\u003e, \u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e34\u003c/span\u003e]. Each \u003cem\u003eP\u003c/em\u003e-helicity enantiomer is found to be associated with adjacent \u003cem\u003eM\u003c/em\u003e-helicity enantiomer through weak intermolecular interactions to form a 2D supramolecular structure (Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003eb).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eYellow crystals of complex \u003cb\u003e1\u003c/b\u003e were obtained via slow solvent evaporation of \u003cb\u003eL\u003c/b\u003e and HgI\u003csub\u003e2\u003c/sub\u003e in the solution of MeOH/DMF (\u003cem\u003eV\u003c/em\u003e/\u003cem\u003eV\u003c/em\u003e\u0026thinsp;=\u0026thinsp;4:3). The crystals crystallize in a monoclinic crystal system with \u003cem\u003eC\u003c/em\u003e2/\u003cem\u003ec\u003c/em\u003e space group, and the asymmetric unit is comprised of two HgI\u003csub\u003e2\u003c/sub\u003e and a ligand \u003cb\u003eL\u003c/b\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003ea). Each central Hg(II) ion is four-coordinated with two I\u003csup\u003e\u0026ndash;\u003c/sup\u003e anions and two nitrogen atoms (N1 and N2) from the 1,8-naphthyridine units, leading to a distorted tetrahedral configuration with \u003cem\u003eτ\u003c/em\u003e\u003csub\u003e4\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.71 (\u003cem\u003eτ\u003c/em\u003e\u003csub\u003e4\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0 for a square planar geometry configuration, and \u003cem\u003eτ\u003c/em\u003e\u003csub\u003e4\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;1 for a perfect tetrahedral geometry configuration) [\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e]. The bond lengths of N\u0026ndash;Hg and I\u0026ndash;Hg vary from 2.512 to 2.759 \u0026Aring;, and the bond angles around the central Hg(II) ion are in the range of 51.22\u0026ndash;147.56\u0026deg;, which are similar to other tetrahedral HgI\u003csub\u003e2\u003c/sub\u003e complexes [\u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e36\u003c/span\u003e, \u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e37\u003c/span\u003e]. In the packing structure, adjacent ligands of opposite helicity are linked through weak interactions to form a 3D structure (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003eb).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eWhen the counter anion was changed from I\u003csup\u003e\u0026minus;\u003c/sup\u003e to Br\u003csup\u003e\u0026minus;\u003c/sup\u003e, complex \u003cb\u003e2\u003c/b\u003e was obtained with a different configuration from \u003cb\u003e1\u003c/b\u003e. The complex crystallizes in a triclinic crystal system with \u003cem\u003eP\u003c/em\u003eī space group, and the asymmetric unit is comprised of two HgBr\u003csub\u003e2\u003c/sub\u003e and a ligand \u003cb\u003eL\u003c/b\u003e. Each Hg(II) ion in \u003cb\u003e2\u003c/b\u003e is four-coordinated with three Br\u003csup\u003e\u0026minus;\u003c/sup\u003e anions and a nitrogen atom in a distorted tetrahedral geometry (\u003cem\u003eτ\u003c/em\u003e\u003csub\u003e4\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.76 for Hg1 center and \u003cem\u003eτ\u003c/em\u003e\u003csub\u003e4\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.71 for Hg2 center). Of the three Br\u003csup\u003e\u0026minus;\u003c/sup\u003e anions, one acts as a terminal ligand and the other two act as \u0026micro;\u003csub\u003e2\u003c/sub\u003e-bridging ligands between two Hg(II) ions to establish a Hg\u0026ndash;(Br)\u003csub\u003e2\u003c/sub\u003e\u0026ndash;Hg quadrilateral (Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003ea). The bond lengths of Hg1\u0026ndash;N1 and Hg2\u0026ndash;N9 are 2.282(5) and 2.324(5) \u0026Aring;, and the bond lengths of Hg\u0026ndash;Br vary from 2.5251 to 2.9655 \u0026Aring;, which are consistent with previously reported complexes [\u003cspan citationid=\"CR38\" class=\"CitationRef\"\u003e38\u003c/span\u003e, \u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e39\u003c/span\u003e]. The bond angles around Hg1 and Hg2 centers vary from 88.05 to 134.40\u0026deg;, and the Hg\u0026middot;\u0026middot;\u0026middot;Hg distance bridged by ligand \u003cb\u003eL\u003c/b\u003e is 3.882 \u0026Aring;. Similarly, adjacent ligands of opposite helicity form a 3D supramolecular structure through weak intermolecular hydrogen bonds (Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003eb).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eYellow crystals of complex \u003cb\u003e3\u003c/b\u003e were obtained via slow solvent evaporation of HgCl\u003csub\u003e2\u003c/sub\u003e and ligand \u003cb\u003eL\u003c/b\u003e in the solution of MeOH/DMF (\u003cem\u003eV\u003c/em\u003e/\u003cem\u003eV\u003c/em\u003e\u0026thinsp;=\u0026thinsp;1:1). The complex exists as a binuclear 44-membered metallamacrocycle in a twisted figure-eight conformation (Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003ea). Each central Hg(II) ion is four-coordinated with two Cl\u003csup\u003e\u0026ndash;\u003c/sup\u003e anions and two nitrogen atoms from adjacent 1,8-naphthyridine units in a tetrahedral configuration with \u003cem\u003eτ\u003c/em\u003e\u003csub\u003e4\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.60. The bond lengths of Hg\u0026ndash;Cl and Hg\u0026ndash;N are in the range of 2.379 and 2.650 \u0026Aring;, and the bond angles around the Hg(II) ion vary from 90.33 to 152.04\u0026deg;, which are similar to the related complexes [\u003cspan citationid=\"CR40\" class=\"CitationRef\"\u003e40\u003c/span\u003e, \u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e41\u003c/span\u003e]. Each macrocycle exists as a mesomer of one \u003cem\u003eM\u003c/em\u003e-helicity enantiomer and one \u003cem\u003eP\u003c/em\u003e-helicity enantiomer, which is further connected to adjacent macrocycle through weak intermolecular interactions to form 1D channels in the 3D network (Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003eb).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eIn this work, three HgX\u003csub\u003e2\u003c/sub\u003e (X\u0026thinsp;=\u0026thinsp;I\u003csup\u003e\u0026minus;\u003c/sup\u003e, Br\u003csup\u003e\u0026minus;\u003c/sup\u003e, and Cl\u003csup\u003e\u0026minus;\u003c/sup\u003e) salts were used to synthesize complexes \u003cb\u003e1\u003c/b\u003e\u0026thinsp;\u0026minus;\u0026thinsp;\u003cb\u003e3\u003c/b\u003e under similar conditions. It is observed that the Hg(II) ions exhibit different coordination environments in complexes \u003cb\u003e1\u003c/b\u003e\u0026thinsp;\u0026minus;\u0026thinsp;\u003cb\u003e3\u003c/b\u003e due to the different anions used (Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e). In complex \u003cb\u003e1\u003c/b\u003e, each Hg(II) ion coordinates to both of the two nitrogen atoms in the 1,8-naphthyridine units. In complex \u003cb\u003e2\u003c/b\u003e, each Hg(II) ion only coordinates to the nitrogen atoms at 8-position of the 1,8-naphthyridine units. Upon replacement of I\u003csup\u003e\u0026minus;\u003c/sup\u003e or Br\u003csup\u003e\u0026minus;\u003c/sup\u003e with Cl\u003csup\u003e\u0026minus;\u003c/sup\u003e, a 44-membered metallamacrocycle was obtained in complex \u003cb\u003e3\u003c/b\u003e, in which one of the Hg(II) ions coordinates to the nitrogen atom at 1-position of the 1,8-naphthyridine units, while the other one coordinates to the nitrogen atom at 8-position of the 1,8-naphthyridine units. All of these Hg(II) ions in the three complexes are four-coordinated in a distorted tetrahedral configuration. The structural differences of complexes \u003cb\u003e1\u003c/b\u003e\u0026thinsp;\u0026minus;\u0026thinsp;\u003cb\u003e3\u003c/b\u003e may be attributed to the different ionic radius of the anions. In addition, by comparing the coordination configurations of complexes \u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e3\u003c/b\u003e, it is noteworthy that complexes \u003cb\u003e1\u003c/b\u003e and \u003cb\u003e2\u003c/b\u003e are racemic, while complex \u003cb\u003e3\u003c/b\u003e is mesomeric, revealing their structural differences in chiral self-assembly.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003ePXRD and TGA analysis\u003c/h2\u003e \u003cp\u003eThe PXRD patterns of the three synthesized complexes are in good agreement with the simulated patterns, showing good phase purities of complexes \u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e3\u003c/b\u003e (Fig. S7). The thermal stabilities of complexes \u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e3\u003c/b\u003e were recorded in the range of 25\u0026thinsp;\u0026minus;\u0026thinsp;800 ℃ (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003e). Complexes \u003cb\u003e1\u003c/b\u003e and \u003cb\u003e2\u003c/b\u003e are stable below 220 ℃, then they begin to decompose and loss weight obviously in the range of 220\u0026thinsp;\u0026minus;\u0026thinsp;400 ℃. Complex \u003cb\u003e3\u003c/b\u003e exhibits a slight weight loss (2.0%) from 25 to 70 ℃, which is relevant to the loss of two lattice water molecules (calculated 2.0%) in the crystals. After further heating, a weight loss of 21.1% can be observed in the range of 250\u0026thinsp;\u0026minus;\u0026thinsp;500 ℃ due to decomposition of the organic framework. The results show that all the complexes have good thermal stability.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e\n\u003ch3\u003eSolid-state luminescence\u003c/h3\u003e\n\u003cp\u003eThe solid-state luminescence of complexes \u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e3\u003c/b\u003e and \u003cb\u003eL\u003c/b\u003e were studied at room temperature (Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003e). Upon excitation at λ\u0026thinsp;=\u0026thinsp;380 nm, the maximum luminescence emission of \u003cb\u003eL\u003c/b\u003e can be observed at 500 nm, which is due to the π\u0026ndash;π* and n\u0026ndash;π* transition [\u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e42\u003c/span\u003e, \u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e43\u003c/span\u003e]. Complex \u003cb\u003e1\u003c/b\u003e shows a maximum luminescence emission peak at 516 nm (λ\u003csub\u003eex\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;390 nm). When excited at the same wavelength, complexes \u003cb\u003e2\u003c/b\u003e and \u003cb\u003e3\u003c/b\u003e show emission maxima at 515 and 518 nm, respectively. These slight red shifts compared with \u003cb\u003eL\u003c/b\u003e should be ascribe to the coordination of \u003cb\u003eL\u003c/b\u003e to Hg(II) ions. In addition, the fluorescence intensity of these three complexes is much lower in comparison with \u003cb\u003eL\u003c/b\u003e, which means that the complexation of ligand \u003cb\u003eL\u003c/b\u003e with Hg(II) ions has a negative effect on the fluorescence intensity.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e\n\u003ch3\u003eMethanol vapor adsorption for the complexes\u003c/h3\u003e\n\u003cp\u003eConsidering the abundant hydrogen bonding sites in the three complexes, we studied the gas adsorption of the three complexes towards methanol vapor at room temperature. The synthesized powder samples were activated in a dynamic vacuum at 373 K for 5 hours to remove the solvent molecules, then the adsorption isotherms towards methanol vapor were recorded at room temperature (298 K). As shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003e, the largest quantity adsorbed of the three complexes towards methanol vapor at \u003cem\u003eP\u003c/em\u003e/\u003cem\u003eP\u003c/em\u003e\u003csub\u003e\u003cem\u003e0\u003c/em\u003e\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.99 increases as follows: \u003cb\u003e1\u003c/b\u003e (25.2 cm\u003csup\u003e3\u003c/sup\u003e/g STP)\u0026thinsp;\u0026lt;\u0026thinsp;\u003cb\u003e2\u003c/b\u003e (28.8 cm\u003csup\u003e3\u003c/sup\u003e/g STP )\u0026thinsp;\u0026lt;\u0026thinsp;\u003cb\u003e3\u003c/b\u003e (65.5 cm\u003csup\u003e3\u003c/sup\u003e/g STP). Base on the good adsorption performance, it is inferred that the methanol molecules mainly bind to the ligands in the complexes through hydrogen bonds [\u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e29\u003c/span\u003e, \u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e, \u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e45\u003c/span\u003e]. Furthermore, the experimental results show that with the increase of the cavity (\u003cb\u003e1\u003c/b\u003e\u0026thinsp;\u0026lt;\u0026thinsp;\u003cb\u003e2\u003c/b\u003e\u0026thinsp;\u0026lt;\u0026thinsp;\u003cb\u003e3\u003c/b\u003e) in the assembly structures of the complexes, more methanol molecules form hydrogen bonds with the ligand, which leads to the increase of the adsorption of methanol vapor.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e"},{"header":"Conclusions","content":"\u003cp\u003eIn summary, a helical Schiff base compound (\u003cb\u003eL\u003c/b\u003e) containing both 1,8-naphthyridine and PDA units was synthesized and characterized. The crystal structure shows a racemic conformation with equal amounts of \u003cem\u003eP\u003c/em\u003e- and \u003cem\u003eM\u003c/em\u003e-helicity enantiomers in the compound. Furthermore, under similar solvent evaporation conditions, the assembly of this ligand with Hg(II) halide (HgI\u003csub\u003e2\u003c/sub\u003e, HgBr\u003csub\u003e2\u003c/sub\u003e, and HgCl\u003csub\u003e2\u003c/sub\u003e) resulted in three complexes with different coordination configuration, which may be attributed to the different ionic radius of the halide anions. In addition, the gas adsorption of the synthesized complexes towards methanol vapor was investigated. The results showed that complex \u003cb\u003e3\u003c/b\u003e exhibited an obviously better adsorption capacity towards methanol vapor over complexes \u003cb\u003e1\u003c/b\u003e and \u003cb\u003e2\u003c/b\u003e, which can be attributed to the larger cavity in the assembly structure of complex \u003cb\u003e3\u003c/b\u003e.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e \u003cstrong\u003eCompeting interests\u003c/strong\u003e \u003cp\u003eThe authors declare no competing interests.\u003c/p\u003e \u003c/p\u003e\u003ch2\u003eFunding\u003c/h2\u003e \u003cp\u003eThis work was financially supported by the National Natural Science Foundation of China (22461009), the Guizhou Provincial Science and Technology Projects (ZK[2024]080), and the Guizhou Provincial Key Laboratory Platform Project (ZSYS[2025]008).\u003c/p\u003e\u003ch2\u003eAuthor Contribution\u003c/h2\u003e\u003cp\u003eC. Huang synthesized L and the three complexes and determined the crystal structures of these compounds. T. Jiang tested the solid-state luminescence and vapor adsorption properties of the complexes. J.-H. Lu analyzed the properties of the complexes and wrote the main manuscript text. All authors reviewed the manuscript.\u003c/p\u003e\u003ch2\u003eData Availability\u003c/h2\u003e\u003cp\u003eData is provided within the manuscript or supplementary information files.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eGu Y, Wu Y, Li L, Chen W, Li F, Kitagawa S (2017) Controllable Modular Growth of Hierarchical MOF-on-MOF Architectures. 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Inorg Chim Acta 510:119702. \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1016/j.ica.2020.119702\u003c/span\u003e\u003cspan address=\"10.1016/j.ica.2020.119702\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"},{"header":"Scheme ","content":"\u003cp\u003eSchemes 1 and 2 are available in the Supplementary Files section\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":"structural-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"stuc","sideBox":"Learn more about [Structural Chemistry](https://www.springer.com/journal/11224)","snPcode":"11224","submissionUrl":"https://submission.nature.com/new-submission/11224/3","title":"Structural Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Schiff base, Racemic ligand, Hg(II) complex, Crystal structure, Methanol vapor adsorption","lastPublishedDoi":"10.21203/rs.3.rs-5731921/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-5731921/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThe Schiff base condensation reaction between precursor diamine \u003cem\u003eN\u003c/em\u003e,\u003cem\u003eN'\u003c/em\u003e-bis(2-aminophenyl)-pyridine-2,6-dicarboxamide and 1,8-naphthyridine-2-carbaldehyde yielded a racemic compound (\u003cb\u003eL\u003c/b\u003e\u003csup\u003e\u003cb\u003eP\u003c/b\u003e\u003c/sup\u003e/\u003cb\u003eL\u003c/b\u003e\u003csup\u003e\u003cb\u003eM\u003c/b\u003e\u003c/sup\u003e), which was characterized by \u003csup\u003e1\u003c/sup\u003eH/\u003csup\u003e13\u003c/sup\u003eC NMR, infrared spectroscopy, elemental analysis, and single crystal X-ray diffraction. Three complexes, [Hg\u003csub\u003e2\u003c/sub\u003e\u003cb\u003eL\u003c/b\u003eI\u003csub\u003e4\u003c/sub\u003e] (\u003cb\u003e1\u003c/b\u003e), [Hg\u003csub\u003e2\u003c/sub\u003e\u003cb\u003eL\u003c/b\u003eBr\u003csub\u003e4\u003c/sub\u003e] (\u003cb\u003e2\u003c/b\u003e), and [Hg\u003csub\u003e2\u003c/sub\u003e\u003cb\u003eL\u003c/b\u003e\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e4\u003c/sub\u003e]‧2H\u003csub\u003e2\u003c/sub\u003eO (\u003cb\u003e3\u003c/b\u003e) with different coordination configurations were obtained from the reaction of this compound with HgX\u003csub\u003e2\u003c/sub\u003e (X\u0026thinsp;=\u0026thinsp;I\u003csup\u003e\u0026minus;\u003c/sup\u003e, Br\u003csup\u003e\u0026minus;\u003c/sup\u003e, and Cl\u003csup\u003e\u0026minus;\u003c/sup\u003e), respectively, and their crystal structures and coordination geometries were determined via single crystal X-ray diffraction techniques. Both \u003cb\u003e1\u003c/b\u003e and \u003cb\u003e2\u003c/b\u003e exist as dinuclear complexes with a 1:2 molar ratio of \u003cb\u003eL\u003c/b\u003e and Hg(II), while \u003cb\u003e3\u003c/b\u003e exists as a 44-membered metallamacrocycle with a 1:1 molar ratio of \u003cb\u003eL\u003c/b\u003e and Hg(II). The structural diversity of these three complexes indicates that the counter anions have significant effects on the structural topology. In addition, the solid-state luminescence and the gas adsorption of these complexes towards methanol vapor at room temperature were investigated.\u003c/p\u003e","manuscriptTitle":"Synthesis, structural diversity, and methanol vapor adsorption properties of three Hg(II) halide complexes derived from a helical Schiff base","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-01-01 16:36:23","doi":"10.21203/rs.3.rs-5731921/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-01-24T10:48:59+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-01-17T11:32:23+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"28140910155219549660575288161356760177","date":"2025-01-06T12:15:36+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"164498880335936983700847409283978690749","date":"2025-01-02T08:04:51+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2024-12-30T15:37:58+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2024-12-30T15:31:10+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2024-12-30T13:37:52+00:00","index":"","fulltext":""},{"type":"submitted","content":"Structural Chemistry","date":"2024-12-30T01:23:03+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"structural-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"stuc","sideBox":"Learn more about [Structural Chemistry](https://www.springer.com/journal/11224)","snPcode":"11224","submissionUrl":"https://submission.nature.com/new-submission/11224/3","title":"Structural Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"8b884d7b-bdc4-4cfd-9b9b-0d9df4e44ffa","owner":[],"postedDate":"January 1st, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-02-24T16:05:53+00:00","versionOfRecord":{"articleIdentity":"rs-5731921","link":"https://doi.org/10.1007/s11224-025-02473-y","journal":{"identity":"structural-chemistry","isVorOnly":false,"title":"Structural Chemistry"},"publishedOn":"2025-02-21 15:57:26","publishedOnDateReadable":"February 21st, 2025"},"versionCreatedAt":"2025-01-01 16:36:23","video":"","vorDoi":"10.1007/s11224-025-02473-y","vorDoiUrl":"https://doi.org/10.1007/s11224-025-02473-y","workflowStages":[]},"version":"v1","identity":"rs-5731921","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-5731921","identity":"rs-5731921","version":["v1"]},"buildId":"XKTyCvWXoU3ODBz1xrDgd","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}