Syntheses, Crystal Structures and Properties of Two Coordination Polymers Based on Bisbenzimidazole

摘要
图/表
参考文献
相关文章 (15)

全文: PDF (805 KB) HTML (1 KB)
输出: BibTeX | EndNote (RIS)

摘要 Two novel coordination polymers Bim(C=O)CuI]2 (1) and [Bim(C=O)CdCl2]2 (2) based on the flexible ligand bis(1H-benzo[d]imidazol-2-yl)methane (Bim) were synthesized via volatilization method. They crystalize in monoclinic and triclinic crystal systems and adopt space group of P21/c and P , respectively. The compounds were characterized by elemental analysis, infrared spectroscopy and powder X-ray diffraction analysis. Interestingly, methylene (-CH2-) in Bim was oxidized to carbonyl (C=O), which increases its extra-cyclic conjugation effect. For 1 and 2, their maximum emission wavelength of fluorescence around 440 and 475 nm indicates the potential as promising light-emissive materials. Meaningfully, Co2+ ion shows a quenching effect on the fluorescence of compound 1. Besides, both compounds possess remarkable structure stability.

	服务

	把本文推荐给朋友
	加入我的书架
	加入引用管理器
	E-mail Alert
	RSS
	作者相关文章
	贾强强
	万敏
	佟亮
	邢正
	王国喜
	陈立庄

关键词 ： bisbenzimidazole ligand, crystal structure, fluorescence, methylene, carbonyl

Abstract：Two novel coordination polymers Bim(C=O)CuI]2 (1) and [Bim(C=O)CdCl2]2 (2) based on the flexible ligand bis(1H-benzo[d]imidazol-2-yl)methane (Bim) were synthesized via volatilization method. They crystalize in monoclinic and triclinic crystal systems and adopt space group of P21/c and P , respectively. The compounds were characterized by elemental analysis, infrared spectroscopy and powder X-ray diffraction analysis. Interestingly, methylene (-CH2-) in Bim was oxidized to carbonyl (C=O), which increases its extra-cyclic conjugation effect. For 1 and 2, their maximum emission wavelength of fluorescence around 440 and 475 nm indicates the potential as promising light-emissive materials. Meaningfully, Co2+ ion shows a quenching effect on the fluorescence of compound 1. Besides, both compounds possess remarkable structure stability.

Key words： bisbenzimidazole ligand crystal structure fluorescence methylene carbonyl

收稿日期: 2020-12-10 出版日期: 2021-07-02

基金资助:Supported by the National Natural Science Foundation of China (NSFC21671084)

通讯作者: clz1977@sina.com E-mail: clz1977@sina.com

引用本文:

贾强强;万敏;佟亮;邢正;王国喜;陈立庄. Syntheses, Crystal Structures and Properties of Two Coordination Polymers Based on Bisbenzimidazole[J]. 结构化学, 2021, 40(7): 871-877.
JIA Qiang-Qiang;WAN Min;TONG Liang;XING Zheng;WANG Guo-Xi;CHEN Li-Zhuang . Syntheses, Crystal Structures and Properties of Two Coordination Polymers Based on Bisbenzimidazole. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 40(7): 871-877.

链接本文:

http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2021/V40/I7/871

REFERENCES
(1) 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.
(2) Chen, L. Z.; Liao, W. Q.; Ai, Y.; Li, J. Y.; Deng, S. Y.; Hou, Y. L.; Tang, Y. Y. Precise molecular design toward organic-inorganic zinc chloride ABX3 ferroelectrics. J. Am. Chem. Soc. 2020, 142, 6236–6243.
(3) Liu, H. Y.; Zhang, H. Y.; Chen, X. G.; Xiong, R. G. Molecular design principles for ferroelectrics: ferroelectrochemistry. J. Am. Chem. Soc. 2020, 142, 15205–15218.
(4) Li, J. Y.; Xu, Q. L.; Ye, S. Y.; Tong, L.; Chen, X.; Chen, L. Z. A multiaxial molecular ferroelectric with record high TC designed by intermolecular interaction modulation. Chem. Commun. 2021, 57, 943–946.
(5) Su, Y. J.; Cui, Y. L.; Wang, Y.; Lin, R. B.; Zhang, W. X.; Zhang, J. P.; Chen, X. M. Copper(I) 2-isopropylimidazolate: supramolecular isomerism, isomerization, and luminescent properties. Cryst. Growth. Des. 2015, 15, 1735–1739.
(6) Chen, Z. X.; Jiang, Y. W.; Zhang, L.; Guo, Y. L.; Ma, D. W. Oxalic diamides and tert-butoxide: two types of ligands enabling practical access to alkyl aryl ethers via Cu-catalyzed coupling reaction. J. Am. Chem. Soc. 2019, 141, 3541–3549.
(7) Zhang, X. L.; Jin, M. F.; Feng, Y. Q. Syntheses, crystal structures and luminescent properties of two new Zn(II) coordination polymers based on rigid biphenyldicarboxylate. Inorg. Chem. Comm. 2011, 14, 952–955.
(8) Chen, C. H.; Shi, J.; Tang, C. W. Recent developments in molecular organic electroluminescent materials. Macromol. Res. 1998, 125, 1–48.
(9) Xu, G. C.; Qin, H.; Okamura, T. K.; Bai, Z. S.; Ding, J.; Huang, Y. Q.; Liu, G. X. Cadmium(II) coordination polymers with flexible tetradentate ligand 1,2,4,5-tetrakis(imidazol-1-ylmethyl)benzene: anion effect and reversible anion exchange property. CrystEngComm. 2008, 11, 205–374.
(10) Liu, X. C.; Guo, X. L.; Niu, Y. Y.; Wang, Q. L.; Cui, Q. Synthesis and structure of a CdI2 coordination polymer with
1,4-bis(benzimidazole-1-yl-methylene)benzene (bbmb). J. Chem. Crystallogr. 2009, 39, 147–150.
(11) Dong, B. X.; Xu, Q. Structural investigation of flexible 1,4-bis(1,2,4-triazol-1-ylmethyl)benzene ligand in keggin-based polyoxometalate frameworks. Cryst. Growth. Des. 2009, 9, 2776–2782.
(12) Hou, G. F.; Bi, L. H.; Li, B.; Wu, L. X. Reaction controlled assemblies of polyoxotungstates (-molybdates) and coordination polymers. Inorg. Chem. 2010, 49, 6474–6483.
(13) Xu, C. Y.; Li, L. K.; Wang, Y. P.; Guo, Q. Q.; Hou, H. W. Three-dimensional Cd(II) coordination polymers based on semirigid bis(methylbenzimidazole) and aromatic polycarboxylates: syntheses, popological structures and photoluminescent properties. Cryst. Growth Des. 2011, 11, 4667–4675.
(14) Meng, X. R.; Song, Y. L.; Hou, H. W. Hydrothermal syntheses, crystal structures, and characteristics of a series of Cd−btx coordination polymers (btx = 1,4-bis(triazol-1-ylmethyl)benzene). Inorg. Chem. 2004, 43, 3528−3536.
(15) Hou, H. W.; Ma, K.; Zhao, Y. G.; Han, X.; Meng, X. R. Interestingly pH-responsible behavior in benzothiadiazole-derived coordination polymer constructed via a situ click synthesis. Cryst. Growth. Des. 2018, 18, 12, 7419–7425.
(16) Zhao, Y. L.; Wu, C.; Qiu, P. L.; Li, X. P.; Wang, Q.; Chen, J. S. New benzimidazole-based bipolar sosts: highly efficient phosphorescent and thermally activated delayed fluorescent OLEDs employing the same device structure. ACS Appl. Mater. Interfaces 2016, 8, 4, 2635–2643.
(17) Avishek, D.; SaibalBera, K. B. Cocrystals and salts of pyridine-3,5-bis(1-methyl-benzimidazole-2-yl) with pyromellitic acid: aromatic guest inclusion and separation via benzimidazole-carboxylic acid heterosynthon. Cryst. Growth. Des. 2015, 15, 1, 318–325.
(18) Sachio, H.; Satoshi, I.; Aoyagi, S. Hydrogen-bonded architectures and field-induced polarization switching in bridged bis(benzimidazole) crystals. Cryst. Growth. Des. 2019, 19, 1, 328–335.
(19) Yao, H. C.; Li, M. M.; Yang, G. S.; Li, Z. J.; Zhu, Y. Ketonization of methylene of bis(benzimidazol-2-yl)methane by molecular oxygen under the catalysis of cobalt(II) ion. Inorg. Chim. Acta 2007, 360, 3959–3964.
(20) Sobkowiak, A.; Sawyer, D. T. Cobalt(II)-induced activation of dioxygen for the dehydrogenation of N-methylanilines and benzyl alcohol. J. Am. Chem. Soc. 1991, 113, 9520–9523.
(21) Costa, P.; Lohmiller, T.; Trosien, I.; Savitsky, A.; Lubitz, W.; Fernandez-Oliva, M.; Sander, W. Light and temperature control of the spin state of bis(p-methoxyphenyl)carbene: a magnetically bistable carbene. J. Am. Chem. Soc. 2016, 138, 1622–1629.
(22) Kang, M. P.; Luo, D. P.; Lin, Z. E.; Thielec, G.; Stefanie, D. Crystalline beryllium carboxylate frameworks containing inorganic chains of BeO4 tetrahedra. CrystEngComm. 2013, 13, 1845.
(23) Hao, P. F.; Zhu, H. H.; Pang, Y.; Fu, Y. L. The impact of positional isomerism on electronic and photochromic properties of 1D zinc-based naphthalene diimide coordination polymers. CrystEngComm. 2020, 20, 3371–3377.
(24) Hao, P. F.; Zhu, H. H.; Pang, Y.; Fu, Y. L. Positional isomerism controlled electronic and photochromic properties of naphthalene diimide-based chlorozincate hybrids. Cryst. Growth. Des. 2020, 20, 345–351.
(25) Chrisstoffels, L. A. J.; Adronov, A.; Fréchet, J. M. J. Surface-confined light harvesting, energy transfer, and amplification of fluorescence emission in chromophore-labeled self-assembled monolayers. Angew Chem. Int. Engl. 2000, 39, 2163–2167.