Hydrothermal Synthesis, Crystal Structure and Properties of 1D Zigzag Chain Zinc(II) Coordination Polymer Constructed from Nicotinic Acid and 1,4-Bis(imidazol-1-ylmethyl)benzene

A zinc–nicotinate complex, {[Zn(na)2(µ-pbix)]∙H2O}n (1), was obtained from the reaction of zinc(II) acetate with nicotinic acid (Hna) and 1,4-bis(imidazol-1-ylmethyl)benzene (pbix) in water at 120 °C under hydrothermal conditions and characterized by elemental analysis, IR spectroscopy, single crystal and powder X-ray diffraction. The thermal stability and luminescent property for 1 were also reported. The asymmetric unit of 1 consists of one zinc(II) center, one pbix ligand, two na anions and one non-coordinated water molecule, giving a formula of {[Zn(na)2(µ-pbix)]∙H2O}n. The Zn(II) ion is coordinated by two nitrogen atoms from two different 1,4-bis(imidazol-1-ylmethyl)benzene ligands and two oxygen atoms from two different nicotinate (na) anions, thus showing a distorted tetrahedral geometry. The adjacent Zn(II) ions are linked into an infinite 1D zigzag chain by 1,4-bis(imidazol-1-ylmethyl)benzene ligands. Grand canonical Monte Carlo (GCMC) simulations were also performed to compute single-component H2 adsorption isotherms at a pressure range of 0.01–100 bar and at 298 K and 77 K. The maximum H2 uptake in 1 was found as 68 cm3/ g STP at 100 bar and 77 K. This study will be useful to accelerate the hydrothermal synthesis of new coordination polymers for gas storage applications.

Keywords:

Coordination polymer, nicotinic acid, N-donor ligand zinc(II) complex, molecular simulations,

PDF

___

1. Mai HD, Rafiq K, Yoo H. Nano Metal-Organic Framework-Derived Inorganic Hybrid Nanomaterials: Synthetic Strategies and Applications. Chem-Eur J. 2017;23(24):5631-51.
2. Janiak C. Engineering coordination polymers towards applications. Dalton T. 2003:2781-804.
3. Arici M, Yesilel OZ, Keskin S, Sahin O. Gas adsorption/separation properties of metal directed self-assembly of two coordination polymers with 5-nitroisophthalate. J Solid State Chem. 2014;210(1):280-6.
4. Semerci F, Yesilel OZ, Soylu MS, Keskin S, Buyukgungor O. A two-dimensional photoluminescent cadmium(II) coordination polymer containing a new coordination mode of pyridine-2,3-dicarboxylate: Synthesis, structure and molecular simulations for gas storage and separation applications. Polyhedron. 2013;50(1):314-20.
5. Guang-Xiang L. Synthesis, Crystal Structure and Magnetic Property of a Copper(II) Coordination Polymer Constructed from Nicotinic Acid. Chinese J Inorg Chem. 2013;29(9):1914-20.
6. Ay B, Yag G, Yildiz E, Rheingold AL. Hydrothermal synthesis and characterization of {[Ni-2(na)4( µ-H2O)]∙2H2O}n (HNA = nicotinic acid) and its heterogeneous catalytic effect. Polyhedron. 2015;88:164-9.
7. Zhang XJ, Wang WJ, Hu ZJ, Wang GN, Uvdal KS. Coordination polymers for energy transfer: Preparations, properties, sensing applications, and perspectives. Coordin Chem Rev. 2015;284:206-35.
8. Batten SR, Chen BL, Vittal JJ. Coordination Polymers/MOFs: Structures, Properties and Applications. Chempluschem. 2016;81(8):669-70.
9. Lou BY, He FD. Coordination polymers as potential solid forms of drugs: three zinc(II) coordination polymers of theophylline with biocompatible organic acids. New J Chem. 2013;37(2):309-16.
10. Yan L, Liu W, Li CB, Wang YF, Ma L, Dong QQ. Hydrogen bonded supra-molecular framework in inorganic-organic hybrid compounds: Syntheses, structures, and photoluminescent properties. J Mol Struct. 2013;1035:240-6.
11. Chen GF, Cao CZ. Hydrothermal synthesis and structural characterization of a zigzag-chain polymer of {[p-MeBzlPh3P][ZnCl2(NA)]}n (NA = nicotinic acid). J Coord Chem. 2008;61(2):262-9.
12. Nie FM, Wang SY. Synthesis and characterization of two nicotinate-containing cadmium complexes in a tripodal ligand system. J Coord Chem. 2011;64(23):4145-56.
13. Hojnik N, Kristl M, Golobic A, Jaglicic Z, Drofenik M. The synthesis, structure and physical properties of lanthanide(III) complexes with nicotinic acid. Cent Eur J Chem. 2014;12(2):220-6.
14. Liu DS, Sui Y, Chen WT, Feng PY. Two New Nonlinear Optical and Ferroelectric Zn(II) Compounds Based on Nicotinic Acid and Tetrazole Derivative Ligands. Cryst Growth Des. 2015;15(8):4020-5.
15. Song YS, Yan B, Chen ZX. Hydrothermal synthesis, crystal structure and luminescence of four novel metal-organic frameworks. J Solid State Chem. 2006;179(12):4037-46.
16. Liu ZX. Synthesis, Crystal Structure and Biological Activity of a Polymeric Silver(I) Complex Derived From Nicotinic Acid. Synth React Inorg M. 2016;46(6):809-13.
17. Vargova Z, Zelenak V, Cisarova I, Gyoryova K. Correlation of thermal and spectral properties of zinc(II) complexes of pyridinecarboxylic acids with their crystal structures. Thermochim Acta. 2004;423(1-2):149-57. 18. Di YY, Hong YP, Kong YX, Yang WW, Tan ZC. Synthesis, characterization, and thermochemistry of the solid state coordination compound Zn(Nic)2∙H2O(s) (Nic = nicotinic acid). J Chem Thermodyn. 2009;41(1):80-3.
19. do Nascimento ALCS, Caires FJ, Gomes DJC, Gigante AC, Ionashiro M. Thermal behaviour of nicotinic acid, sodium nicotinate and its compounds with some bivalent transition metal ions. Thermochim Acta. 2014;575:212-8.
20. Du M, Li CP, Liu CS, Fang SM. Design and construction of coordination polymers with mixed-ligand synthetic strategy. Coordin Chem Rev. 2013;257(7-8):1282-305.
21. Bu XZ, Chen JQ, Hu MZ. A New Luminescent Zn(II) Coordination Polymer Constructed From Nicotinic Acid and 3,5-Diamino-1,2,4-Triazole Ligands. Synth React Inorg M. 2016;46(1):123-6.
22. Qin JS, Yuan S, Wang Q, Alsalme A, Zhou HC. Mixed-linker strategy for the construction of multifunctional metal-organic frameworks. J Mater Chem A. 2017;5(9):4280-91.
23. An Z, Gao J, Zhu L. Isomeric luminescent Zn(II) coordination polymers based on pyridinecarboxylate and 5-methyl-1H-tetrazole ligands. J Mol Struct. 2013;1054:234-8.
24. Gao JY, Xiong XH, Chen CJ, Xie WP, Ran XR, Yue ST. Syntheses, Structures, and Fluorescence of Two Novel 2D Zinc(II) Layered Frameworks Based on 3-Amino-1, 2, 4-triazole. Z Anorg Allg Chem. 2013;639(3-4):582-6.
25. Liu DS, Huang XH, Huang CC, Huang GS, Chen JZ. Synthesis, crystal structures and properties of three new mixed-ligand d(10) metal complexes constructed from pyridinecarboxylate and in situ generated amino-tetrazole ligand. J Solid State Chem. 2009;182(7):1899-906.
26. Yuan G, Shao KZ, Chen L, Liu XX, Su ZM, Ma JF. Synthesis, crystal structures, and luminescent properties of Cd(II) coordination polymers assembled from semi-rigid multi-dentate N-containing ligand. J Solid State Chem. 2012;196:87-92.
27. Hu JM, Zhao YQ, Yu BY, Van Hecke K, Cui GH. Synthesis and Characterization of Two Distinct 2D Nickel(II) Coordination Polymers From Dicarboxylate and Flexible Bis(imidazole) Ligands. Z Anorg Allg Chem. 2016;642(1):41-7.
28. Erer H, Yesilel OZ, Arici M. A Series of Zinc(II) 3D -> 3D Interpenetrated Coordination Polymers Based On Thiophene-2,5-dicarboxylate and Bis(Imidazole) Derivative Linkers. Cryst Growth Des. 2015;15(7):3201-11.
29. Semerci F, Yesilel OZ, Yuksel F. Self-assembly of three new metal organic coordination networks based on 1,2-bis(imidazol-1yl-methyl)benzene. Polyhedron. 2015;102:1-7.
30. Arici M, Yesilel OZ, Tas M. Cd(II)-coordination polymers based on tetracarboxylic acid and diverse bis(imidazole) ligands: Synthesis, structural diversity and photoluminescence properties. J Solid State Chem. 2017;245:146-51.
31. Zou RQ, Abdel-Fattah AI, Xu HW, Zhao YS, Hickmott DD. Storage and separation applications of nanoporous metal-organic frameworks. Crystengcomm. 2010;12(5):1337-53.
32. So YH. Novel Thermoset Polyimidazole Amides. Macromolecules. 1992;25(2):516-20.
33. Tian ZF, Lin JG, Su Y, Wen LI, Liu YM, Zhu HZ, et al. Flexible ligand, structural, and topological diversity: Isomerism in Zn(NO3)2 coordination polymers. Crystal Growth & Design. 2007;7(9):1863-7.
34. Hoskins BF, Robson R, Slizys DA. An infinite 2D polyrotaxane network in Ag2(bix)3(NO3)2 (bix=1,4-bis(imidazol-1-ylmethyl)benzene). Journal of the American Chemical Society. 1997;119(12):2952-3.
35. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H. OLEX2: a complete structure solution, refinement and analysis program. Journal of Applied Crystallography. 2009;42(2):339-41. 36. Sheldrick GM. A short history of SHELX. Acta Crystallographica Section A. 2008;64(1):112-22.
37. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, et al. Mercury: visualization and analysis of crystal structures. J Appl Crystallogr. 2006;39(3):453-7.
38. Allen FH. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr B. 2002;58:380-8.
39. Willems TF, Rycroft C, Kazi M, Meza JC, Haranczyk M. Algorithms and tools for high-throughput geometry-based analysis of crystalline porous materials. Micropor Mesopor Mat. 2012;149(1):134-41.
40. Buch V. Path-Integral Simulations of Mixed Para-D2 and Ortho-D2 Clusters - the Orientational Effects. Abstr Pap Am Chem S. 1994;208:119-Phys.
41. Rappe AK, Casewit CJ, Colwell KS, Goddard WA, Skiff WM. Uff, a Full Periodic-Table Force-Field for Molecular Mechanics and Molecular-Dynamics Simulations. J Am Chem Soc. 1992;114(25):10024-35.
42. Erucar I, Keskin S. High CO2 Selectivity of an Amine-Functionalized Metal Organic Framework in Adsorption-Based and Membrane-Based Gas Separations. Ind Eng Chem Res. 2013;52(9):3462-72.
43. Garberoglio G. Computer simulation of the adsorption of light gases in covalent organic frameworks. Langmuir. 2007;23(24):12154-8.
44. D. Frenkel, Smit B. Understanding Molecular Simulation. Elsevier Science2001. 664 p. 45. Zelenak V, Vargova Z, Gyoryova K. Correlation of infrared spectra of zinc(II) carboxylates with their structures. Spectrochim Acta A. 2007;66(2):262-72.
46. Wu LJ, Li XX, Wang RH. Synthesis and Characterization of a Silver(I)-indium(III) Heterometallic Metal-organic Framework Based on Nicotinate. Chinese J Struc Chem. 2015;34(11):1703-8.
47. Meng XM, Zhang X, Qi PF, Zong ZA, Jin F, Fan YH. Syntheses, structures, luminescent and photocatalytic properties of various polymers based on a "V"-shaped dicarboxylic acid. Rsc Adv. 2017;7(9):4855-71.