Synthesis, Crystal Structure and Properties of a Copper(I) Coordination Polymer Based on Benzimidazole Derivative
- Corresponding author: Li-Zhuang CHEN, clz1977@sina.com
Citation:
Qiang-Qiang JIA, Jun-Yi LI, Hao-Xi ZHANG, Li-Zhuang CHEN, Guo-Xi WANG. Synthesis, Crystal Structure and Properties of a Copper(I) Coordination Polymer Based on Benzimidazole Derivative[J]. Chinese Journal of Structural Chemistry,
;2020, 39(11): 2021-2026.
doi:
10.14102/j.cnki.0254–5861.2011–2739
Rouffet, M.; de Oliveira, C. A. F.; Udi, Y.; Agrawal, A.; Sagi, I.; McCammon, J. A.; Cohen, S. M. From sensors to silencers: quinoline- and benzimidazole-sulfonamides as inhibitors for zinc proteases. J. Am. Chem. Soc. 2010, 132, 8232–8233.
doi: 10.1021/ja101088j
Liu, H. Y.; Wu, H.; Ma, J. F.; Liu, Y. Y.; Liu, B.; Yang, J. Syntheses, structures, and photoluminescence of zinc(II) coordination polymers based on carboxylates and flexible bis-[(pyridyl)-benzimidazole] ligands. Cryst. Growth Des. 2010, 10, 4795–4805.
doi: 10.1021/cg100688z
Xue, F.; Kumar, P.; Xu, W.; Mkhoyan, K. A.; Tsapatsis, M. Direct synthesis of 7 nm-thick zinc(II)-benzimidazole-acetate metal-organic framework nanosheets. Chem. Mater. 2017, 30, 69–73.
Combs, A. P.; Zhu, W.; Crawley, M. L.; Glass, B.; Polam, P.; Sparks, R. B.; Metcalf, B. Potent benzimidazole sulfonamide protein tyrosine phosphatase 1B inhibitors containing the heterocyclic (S)-isothiazolidinone phosphotyrosine mimetic. J. Med. Chem. 2006, 49, 3774–3789.
doi: 10.1021/jm0600904
Apohan, E.; Yilmaz, U.; Yilmaz, O.; Serindag, A.; Küçükbay, H.; Yesilada, O.; Baran, Y. Synthesis, cytotoxic and antimicrobial activities of novel cobalt and zinc complexes of benzimidazole derivatives. J. Organomet. Chem. 2017, 828, 52–58.
doi: 10.1016/j.jorganchem.2016.11.020
Chen, L. Z.; Ji, Q.; Dan, Y. Y. Synthesis, structure, and luminescent and dielectric properties of two novel 1D chains based on a T-shaped tripodal ligand 4-(4, 5-dicarboxy-imidazol-2-yl)pyridine loxide. Chin. J. Struct. Chem. 2016, 35, 1728–1735.
Chen, L. Z.; Sun, J.; Ji, Q.; Pan, Q. J.; Huang, Y. Switchable dielectric materials based on 2-methylimidazole. Chin. J. Struct. Chem. 2017, 36, 329–337.
Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. Abnormal ligand binding and reversible ring hydrogenation in the reaction of imidazolium salts with IrH5(PPh3)2. J. Am. Chem. Soc. 2002, 124, 10473–10481.
doi: 10.1021/ja026735g
Wu, T.; Li, D.; Feng, X. L.; Cai, J. W. Trinuclear silver(I) complex with benzimidazole (Hbim) and triphenylphosphine [Ag3(μ-bim)3(PPh3)5]: synthesis, crystal structure and photoluminescence. Inorg. Chem. Commu. 2003, 6, 886–890.
doi: 10.1016/S1387-7003(03)00136-9
Kacar, S.; Unver, H.; Sahinturk, V. A mononuclear copper(II) complex containing benzimidazole and pyridyl ligands: synthesis, characterization, and antiproliferative activity against human cancer cells. Arabian J. Chem. 2019, 0, 1–14.
Zhu, H.; Liu, D.; Li, Y. H.; Cui, G. H. Syntheses, crystal structures, and photocatalytic properties of two zinc(II) coordination polymers based on dicarboxylates and flexible bis(benzimidazole) ligands. Polyhedron 2019, 167, 44–45
doi: 10.1016/j.poly.2019.04.011
Li, X. P.; Zhang, J. Y.; Pan, M.; Zheng, S. R.; Liu, Y.; Su, C. Y. Zero to three dimensional increase of silver(I) coordination assemblies controlled by deprotonation of 1, 3, 5-tri(2-benzimidazolyl)benzene and aggregation of multinuclear building units. Inorg. Chem. 2007, 46, 4617–4625.
doi: 10.1021/ic070309k
Semyonov, O.; Lyssenko, K. A.; Safin, D. A. Copper(II) acetate structures with benzimidazole derivatives. Inorg. Chim. Acta 2019, 488, 238–245.
doi: 10.1016/j.ica.2018.12.054
Park, K. S.; Ni, Z.; Cote, A. P.; Choi, J. Y.; Huang, R.; Uribe-Romo, F. J.; Yaghi, O. M. Exceptional chemical and thermal stability of zeolitic imidazolate frameworks. P. Natl. A. Sci. India. A 2006, 103, 10186–10191.
doi: 10.1073/pnas.0602439103
Song, Y. L.; Jiao, B. J.; Liu, C. M.; Peng, X. L.; Wang, M. M.; Yang, Y.; Du, C. X. Synthesis, structures and luminescent properties of red emissive neutral copper(I) complexes with bisphosphino-substituted benzimidazole. Inorg. Chem. Commu. 2019, 107689.
Devkule, S. S.; Chavan, S. S. Copper(I) complexes of N-(2-quinolynylmethylene)-1H-benzimidazole and triphenylphosphine: synthesis, characterization, luminescence and catalytic properties. Inorg. Chim. Acta 2017, 466, 122–129.
doi: 10.1016/j.ica.2017.05.076
Liu, H. Q.; Tang, J. M.; Jiang, L.; Zheng, T. T.; Wang, X. X.; Lv, X. Efficient domino synthesis of benzimidazole derivatives: copper catalysis versus transition metal-free conditions. Tetrahedron Lett. 2015, 56, 1624–1630.
doi: 10.1016/j.tetlet.2015.01.197
Mohapatra, S. C.; Tehlan, S.; Hundal, M. S.; Mathur, P. Crystal structure and catalytic activity of a copper(II) complex based on a tetradentate bis-benzimidazole diamide ligand. Inorg. Chim. Acta 2008, 361, 1897–1907.
doi: 10.1016/j.ica.2007.10.002
Haneda, S.; Adachi, Y.; Hayashi, M. Copper(I)-2-(2΄-pyridyl)benzimidazole catalyzed N-arylation of indoles. Tetrahedron 2009, 65, 10459–10462.
doi: 10.1016/j.tet.2009.10.014
El-Sherif, A. A.; Shoukry, M. M. Ternary copper(II) complexes involving 2-(aminomethyl)-benzimidazole and some bio-relevant ligands. Equilibrium studies and kinetics of hydrolysis for glycine methyl ester under complex formation. Inorg. Chim. Acta 2007, 360, 473–487.
doi: 10.1016/j.ica.2006.07.108
Wu, T.; Bu, X. H.; Zhang, J.; Feng, P. Y. New zeolitic imidazolate frameworks: from unprecedented assembly of cubic clusters to ordered cooperative organization of complementary ligands. Chem. Mater. 2008, 20, 7377–7382.
doi: 10.1021/cm802400f
Touj, N.; Özdemir, I.; Yaşar, S.; Hamdi, N. An efficient (NHC) copper(I)-catalyst for azide-alkyne cycloaddition reactions for the synthesis of 1, 2, 3-trisubstituted triazoles: click chemistry. Inorg. Chim. Acta 2017, 467, 21–32.
doi: 10.1016/j.ica.2017.06.065
Ayadi, A.; Benmensour, M. A.; Cheret, Y.; Boucekkine, A.; El-Ghayoury, A. Zinc and copper complexes of stilbene iminopyridine ligands with η2-olefin binding mode. J. Organomet. Chem. 2018, 858, 14–22.
doi: 10.1016/j.jorganchem.2018.01.002
Wang, W.; Zhang, L.; Xu, X. B.; Ye, Q. Formation of novel olefin-copper(I) coordination compound dependent on conformation of olefin ligand. Inorg. Chem. Commu. 2011, 14, 626–631.
doi: 10.1016/j.inoche.2011.01.033
Boni, A.; Pampaloni, G.; Peloso, R.; Belletti, D.; Graiff, C.; Tiripicchio, A. Synthesis of copper(I) bis(3, 5-dimethylpyrazolyl)methane olefin complexes and their reactivity towards carbon monoxide. J. Organomet. Chem. 2006, 691, 5602–5609.
doi: 10.1016/j.jorganchem.2006.09.006
Zhao, S.; Wang, Y.; Dong, J.; He, C. T.; Yin, H.; An, P.; Tang, Z. Ultrathin metal organic framework nanosheets for electrocatalytic oxygen evolution. Nat. Energy 2016, 1, 1–10.
Singla, M.; Mohapatra, S. C.; Ahmad, S. Copper nano composites functionalized by bis-benzimidazole diamide ligand: effect of size, co-anion dependent conductivity and band gap studies. Mater. Chem. Phys. 2012, 137, 118–128.
doi: 10.1016/j.matchemphys.2012.08.049
Appa Rao, B. V.; Iqbal, M. Y.; Sreedhar, B. Electrochemical and surface analytical studies of the self-assembled monolayer of 5-methoxy-2-(octadecylthio)benzimidazole in corrosion protection of copper. Electrochim. Acta 2010, 55, 620–631.
doi: 10.1016/j.electacta.2009.09.007
Curtis, M. D.; Cao, J.; Kampf, J. W. Solid-state packing of conjugated oligomers: from π-stacks to the herringbone structure. J. Am. Chem. Soc. 2004, 126, 4318–4328.
doi: 10.1021/ja0397916
Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
Shuyan ZHAO . Field-induced CoⅡ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy4-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
Haiming Wu , Gaya N. Andrew , Rajini Anumula , Zhixun Luo . Corrigendum to 'How ligand coordination and superatomic-states accommodate the structure and property of a metal cluster: Cu4 (dppy)4 Cl2 vs. Cu21 (dppy)10 with altered photoluminescence' [Chin. Chem. Lett. 35 (2024) 108340]. Chinese Chemical Letters, 2024, 35(12): 109912-. doi: 10.1016/j.cclet.2024.109912
Peipei CUI , Xin LI , Yilin CHEN , Zhilin CHENG , Feiyan GAO , Xu GUO , Wenning YAN , Yuchen DENG . Transition metal coordination polymers with flexible dicarboxylate ligand: Synthesis, characterization, and photoluminescence property. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2221-2231. doi: 10.11862/CJIC.20240234