Manganese(Ⅱ) and Copper(Ⅰ) Compounds Based on Two Derivatives of Imidazo[1, 5-a]pyridine: Synthesis, Structures, Magnetic Properties, and Catalytic Activity
- Corresponding author: Ya-Hong LI, liyahong@suda.edu.cn Jin-Lei YAO, jlyao@usts.edu.cn
Citation: Qian ZHANG, Yan-Feng CUI, Xia-Mei ZHANG, Ya-Hong LI, Jin-Lei YAO. Manganese(Ⅱ) and Copper(Ⅰ) Compounds Based on Two Derivatives of Imidazo[1, 5-a]pyridine: Synthesis, Structures, Magnetic Properties, and Catalytic Activity[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220314. doi: 10.14102/j.cnki.0254-5861.2011-3296
Rajnák, C.; Titiš, J.; Moncol, J.; Mičová, R.; Boča, R. Field-induced slow magnetic relaxation in a mononuclear manganese(Ⅱ) complex. Inorg. Chem. 2019, 58, 991−994.
doi: 10.1021/acs.inorgchem.8b02675
Benniston, A. C.; Melnic, S.; Turta, C.; Arauzo, A. B.; Bartolomé, J.; Bartolomé, E.; Harringtonf, R. W.; Probertf, M. R. Preparation and properties of a calcium(Ⅱ)-based molecular chain decorated with manganese(Ⅱ) butterfly-like complexes. Dalton Trans. 2014, 43, 13349−13357.
doi: 10.1039/C4DT01518E
Baron, V.; Gillon, B.; Sletten, J.; Mathoniere, C.; Codjovi, E.; Kahn, O. Interchain interactions and three-dimensional magnetic ordering in Mn(Ⅱ) Cu(Ⅱ) chain compounds; crystal structure and metamagnetic properties of MnCu(pbaOH)(H2O)3·2H2O, with pbaOH = 2-hydroxo-1, 3-propylenebis (oxamato). Inorg. Chim. Acta 1995, 235, 69−76.
doi: 10.1016/0020-1693(95)90047-A
Uchida, K.; Cosquer, G.; Sugisaki, K.; Matsuoka, H.; Sato, K.; Breedlove, B. K.; Yamashita, M. Isostructural M(Ⅱ) complexes (M = Mn, Fe, Co) with field-induced slow magnetic relaxation for Mn and Co complexes. Dalton Trans. 2019, 48, 12023−12030.
doi: 10.1039/C8DT02150C
Yang, E. C.; Chang, Y. Y.; Huang, S. Y.; Hong, L. X.; Lee, G. H.; Sheu, H. S.; Chang, C. K. Novel structures and magnetic properties of two [Mn2] complexes with 2, 4-di-2-pyridyl-2, 4-pentanediol as the ligand. Magnetochemistry 2019, 5, 43.
doi: 10.3390/magnetochemistry5030043
Yu, S. B.; Lippard, S. J.; Shweky, I.; Bino, A. Dinuclear manganese(Ⅱ) complexes with water and carboxylate bridges. Inorg. Chem. 1992, 31, 3502–3504.
doi: 10.1021/ic00043a004
Zhang, S. L.; Li, S. S.; Zeng, S. Y.; Shi, Y.; Wang, D. Q.; Chen, L. Slow magnetic relaxation in O–Se–O bridged manganese(Ⅲ) Schiff base complexes. New J. Chem. 2020, 44, 2408–2413.
doi: 10.1039/C9NJ05837K
Bagaia, R.; Christou, G. The Drosophila of single-molecule magnetism: [Mn12O12(O2CR)16(H2O)4]. Chem. Soc. Rev. 2009, 38, 1011–1026.
doi: 10.1039/b811963e
Su, F.; Zhou, C. Y.; Han, C.; Wu, L. T.; Wu, X.; Sun, L.; Su, J.; Feng, S. S; Lu, L. P.; Zhu, M. L. Binuclear Mn2+ complexes of a biphenyltetracarboxylic acid with variable N-donor ligands: syntheses, structures, and magnetic properties. Cystectomy 2018, 20, 1818–1831.
Akiyama, H., Kato, M.; Sasaki, S.; Tasaki, M.; Asao, E.; Kajikawa, M. Synthesis, and magnetic properties of a binuclear manganese(Ⅱ) complex with two manganese(Ⅱ) ions of C2-twisted octahedral geometry. Polyhedron 2016, 111, 32–37.
doi: 10.1016/j.poly.2016.03.005
Jing, Y.; Zhang, X. M.; Cui, Y. F.; Li, D. W.; Sun, H.; Ge, Y.; Li, Y. H. Two copper complexes based on derivatives of imidazo[1, 5-a]pyridine: syntheses, structures, and catalytic properties. Chin. J. Struct. Chem. 2020, 39, 1057–1062.
Chan, C. K.; Tsai, Y. L.; Chang, M. Y. CuI mediated one-pot cycloacetalization/ketalization of o-carbonyl allylbenzenes: synthesis of benzobicyclo[3.2.1]octane core. Org. Lett. 2017, 19, 1870−1873.
doi: 10.1021/acs.orglett.7b00630
Yang, H.; Liu, Y. L.; Hu D. D. Syntheses, structures, and catalytic activities of copper(Ⅰ) complexes with the ligand 2(4, 5-diphenyl-1H-imidazol-2-yl)pyridine. Z. Anorg. Allg. Chem. 2014, 640, 394–397.
doi: 10.1002/zaac.201300223
Han, Z. P.; Li, Y. H. Solvothermal synthesis, structure and catalytic activity of a mixed-valence CuI/CuII complex with 1-D chain structure. Inorg. Chem. Commun. 2012, 22, 73–76.
doi: 10.1016/j.inoche.2012.05.023
Tan, X.; Li, L.; Zhang, J. Y.; Han, X. R.; Jiang, L.; Li, F. W.; Su, C. Y. Three-dimensional phosphine metal-organic frameworks assembled from Cu(Ⅰ) and pyridyl diphosphine. Chem. Mater. 2012, 24, 480–485.
doi: 10.1021/cm202608f
Fan, W. T.; Yang, X. P.; Lv, H. P.; Wang, X. W.; Wang, Z. Chiral binaphthyl box-copper-catalyzed enantioselective tandem michael-ketalization annulations for optically active aryl and heteroaryl fused bicyclicnonanes. Org. Lett. 2020, 22, 3936−3941.
doi: 10.1021/acs.orglett.0c01221
Ma, H. X.; Du, J.; Zhu, Z. M.; Lu, T.; Su, F.; Zhang, L. C. Controllable assembly, characterization and catalytic properties of a new strandberg-type organophosphotungstate. Dalton Trans. 2016, 45, 1631–1637.
doi: 10.1039/C5DT04412J
Wang, J. P.; Ma, H. X.; Zhang, L. C.; You, W. S.; Zhu, Z. M. Two Strandberg-type organophosphomolybdates: synthesis, crystal structures and catalytic properties. Dalton Trans. 2014, 43, 17172–17176.
doi: 10.1039/C4DT02571G
Tao, D. J.; Li, Z. M.; Cheng, Z.; Hu, N.; Chen, X. S. Kinetics study of the ketalization reaction of cyclohexanone with glycol using brønsted acidic ionic liquids as catalysts. Ind. Eng. Chem. Res. 2012, 51, 16263–16269.
doi: 10.1021/ie302089s
Liu, J. H.; Wei, X. F.; Yu, Y. L.; Song, J. L.; Wang, X. Li, A.; Liu X. W.; Deng, W. Q. Uniform core-shell titanium phosphate nanospheres with orderly open nanopores: a highly active Brønsted acid catalyst. Chem. Commun. 2010, 46, 1670–1672.
doi: 10.1039/b922100j
Deacon, G. B.; Junk, P. C.; Leary, S. G. Novel Heterobimetallic neodymium/calcium 8-quinolinolate complexes prepared directly from the metals. Z. Anorg. Allg. Chem. 2004, 630, 1541–1543.
doi: 10.1002/zaac.200400164
Chen, Y. M.; Li, L.; Chen, Z.; Liu, Y. L.; Hu, H. L.; Chen, W. Q.; Liu, W.; Li. Y. H. Metal-mediated controllable creation of secondary, tertiary, and quaternary carbon centers: a powerful strategy for the synthesis of iron, cobalt, and copper complexes with in situ generated substituted 1-pyridineimidazo[1, 5-a]pyridine ligands. Inorg. Chem. 2012, 51, 9705−9713.
doi: 10.1021/ic300949y
Chen, Y. M.; Li, L.; Cao, Y. Y.; Wu, J.; Gao, Q.; Li, Y. H. CuⅡ-mediated controllable creation of tertiary and quaternary carbon centers: designed assembly and structures of a new class of copper complexes supported by in situ generated substituted 1-pyridineimidazo[1, 5-a]pyridine ligands. CrystEngComm 2013, 15, 2675−2681.
doi: 10.1039/c3ce00012e
Mukherjee, A.; Dhar, S.; Nethaji, M.; Chakravarty, A. R. Ternary iron(Ⅱ) complex with an emissive imidazopyridine arm from Schiff base cyclizations and its oxidative DNA cleavage activity. Dalton Trans. 2005, 349–353.
Huq, F.; Abdullah, A.; Chowdhury, A.; Cheng, H.; Tayyem, H.; Beale, P. Studies on the synthesis and characterization, binding with DNA and activity of cis-bis{imidazo(1, 2-a)-pyridine}-dichloroplatinum(Ⅱ). Asian J. Chem. 2006, 18, 1637–1648.
Bluhm, M. E.; Ciesielski, M.; Görls, H.; Döring, M. Copper-catalyzed oxidative heterocyclization by atmospheric oxygen. Angew. Chem. Int. Ed. 2002, 41, 2962–2965.
doi: 10.1002/1521-3773(20020816)41:16<2962::AID-ANIE2962>3.0.CO;2-6
Deacon, G. B.; Forsyth, C. M.; Junk, P. C.; Kynast, U.; Meyer, G.; Moore, J.; Sierau, J.; Urbatsch, A. Novel rare earth quinolinolate complexes. J. Alloys Compd. 2008, 451, 436–439.
doi: 10.1016/j.jallcom.2007.04.253
Guckian, A. L.; Doering, M.; Ciesielski, M.; Walter, O.; Hjelm, J.; O'Boyle, N. M.; Henry, W.; Browne, W. R.; McGarvey, J. J.; Vos, J. G. Assessment of intercomponent interaction in phenylene bridged dinuclear ruthenium(Ⅱ) and osmium(Ⅱ) polypyridyl complexes. Dalton Trans. 2004, 3943–3949.
Volpi, G.; Garino, C.; Salassa, L.; Fiedler, J.; Hardcastle, K. I.; Gobetto, R.; Nervi, C. Cationic heteroleptic cyclometalated iridium complexes with 1-pyridylimidazo[1, 5-α]pyridine ligands: exploitation of an efficient intersystem crossing. Chem. Eur. J. 2009, 15, 6415–6427.
doi: 10.1002/chem.200801474
Murai, T.; Nagaya, E.; Miyahara, K.; Shibahara, F.; Maruyama, T. Synthesis and characterization of boron complexes of imidazo[1, 5-a]pyridylalkyl alcohols. Chem. Lett. 2013, 42, 828–830.
doi: 10.1246/cl.130274
Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution. University of Göttingen Germany 1997.
Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures from Diffraction Data. University of Göttingen Germany 1997.
Casanova, D.; Llunell, M.; Alemany, P.; Alvarez, S. The rich stereochemistry of eight-vertex polyhedra: a continuous shape measures study. Chem. Eur. J. 2005, 11, 1479–1494.
doi: 10.1002/chem.200400799
Kahn, O. Molecular Magnetism. VCH Publishers, Inc. 1993.
Fei, H. H.; Rogow, D. L.; Oliver, S. R. J. Reversible anion exchange and catalytic properties of two cationic metal-organic frameworks based on Cu(Ⅰ) and Ag(Ⅰ). J. Am. Chem. Soc. 2010, 132, 7202−7209.
doi: 10.1021/ja102134c
Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Xin XIONG , Qian CHEN , Quan XIE . First principles study of the photoelectric properties and magnetism of La and Yb doped AlN. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1519-1527. doi: 10.11862/CJIC.20240064
Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
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
Yifei Zhang , Yuncong Xue , Laiwei Gao , Rui Liao , Feng Wang , Fei Wang . Merging non-covalent and covalent crosslinking: En route to single chain nanoparticles. Chinese Chemical Letters, 2024, 35(6): 109217-. doi: 10.1016/j.cclet.2023.109217
Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
Tiankai Sun , Hui Min , Zongsu Han , Liang Wang , Peng Cheng , Wei Shi . Rapid detection of nanoplastic particles by a luminescent Tb-based coordination polymer. Chinese Chemical Letters, 2024, 35(5): 108718-. doi: 10.1016/j.cclet.2023.108718
Zhenzhong MEI , Hongyu WANG , Xiuqi KANG , Yongliang SHAO , Jinzhong GU . Syntheses and catalytic performances of three coordination polymers with tetracarboxylate ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1795-1802. doi: 10.11862/CJIC.20240081
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
Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
Yinglian LI , Chengcheng ZHANG , Xinyu ZHANG , Xinyi WANG . Spin crossover in [Co(pytpy)2]2+ complexes modified by organosulfonate anions. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1162-1172. doi: 10.11862/CJIC.20240087
Shili Wang , Mamitiana Roger Razanajatovo , Xuedong Du , Shunli Wan , Xin He , Qiuming Peng , Qingrui Zhang . Recent advances on decomplexation mechanisms of heavy metal complexes in persulfate-based advanced oxidation processes. Chinese Chemical Letters, 2024, 35(6): 109140-. doi: 10.1016/j.cclet.2023.109140