Construction of Chiral One-dimensional Chains via Mononuclear Chiral Precursors and Circular Dichroism Properties
- Corresponding author: De-Zheng LIU, liudezheng@hbuas.edu.cn Yong-Sheng YANG, ysyang@wtu.edu.cn Yan-Bo ZHANG, yanboz@163.com
Citation:
Hai-Yan JU, Ming YANG, Gang ZHANG, De-Zheng LIU, Yong-Sheng YANG, Yan-Bo ZHANG. Construction of Chiral One-dimensional Chains via Mononuclear Chiral Precursors and Circular Dichroism Properties[J]. Chinese Journal of Structural Chemistry,
;2021, 40(6): 767-774.
doi:
10.14102/j.cnki.0254–5861.2011–3008
Kang, Y. S.; Lu, Y.; Chen, K.; Zhao, Y.; Wang, P.; Sun, W. Y. Metal-organic frameworks with catalytic centers: from synthesis to catalytic application. Coord. Chem. Rev. 2019, 378, 262−280.
doi: 10.1016/j.ccr.2018.02.009
Shen, J.; Okamoto, Y. Efficient separation of enantiomers using stereoregular chiral polymers. Chem. Rev. 2016, 116, 1094−1138.
doi: 10.1021/acs.chemrev.5b00317
Li, J.; Sculley, J.; Zhou, H. Metal-organic frameworks for separations. Chem. Rev. 2012, 112, 869−932.
doi: 10.1021/cr200190s
Kesanli, B.; Lin, W. B. Chiral porous coordination networks: rational design and applications in enantioselective processes. Coord. Chem. Rev. 2003, 246, 305−326.
doi: 10.1016/j.cct.2003.08.004
Telfer, S. G.; Kuroda, R. 1, 1΄-Binaphthyl-2, 2΄-diol and 2, 2΄-diamino-1, 1΄-binaphthyl: versatile frameworks for chiral ligands in coordination and metallosupramolecular chemistry. Coord. Chem. Rev. 2003, 242, 33−46.
doi: 10.1016/S0010-8545(03)00026-2
Jiao, J. J.; Li, Z. J.; Zhang, H. F. K.; Liu, B. Z.; Cui, Y. Synthesis, structure and characterization of a 3D chiral carboxylate and phosphonate metal-organic framework based on 1, 1΄-biphenol ligand. Chin. J. Struct. Chem. 2018, 9, 1509−1515.
Lin, Z. J.; Slawin, A. M. Z.; Morris, R. E. Chiral induction in the ionothermal synthesis of a 3-D coordination polymer. J. Am. Chem. Soc. 2007, 129, 4880−4881.
doi: 10.1021/ja070671y
Bisht, K. K.; Suresh, E. Spontaneous resolution to absolute chiral induction: pseudo-Kagomé type homochiral Zn(Ⅱ)/Co(Ⅱ) coordination polymers with achiral precursors. J. Am. Chem. Soc. 2013, 135, 15690−15693.
doi: 10.1021/ja4075369
Zhang, J.; Hao, J.; Wei, Y. G.; Xiao, F. P.; Yin, P. C.; Wang, L. S. Nanoscale chiral rod-like molecular triads assembled from achiral polyoxometalates. J. Am. Chem. Soc. 2010, 132, 14−15.
doi: 10.1021/ja907535g
Maity, A.; Gangopadhyay, M.; Basu, A.; Aute, S.; Babu, S. S.; Das, A. Counteranion driven homochiral assembly of a cationic C3-symmetric gelator through ion-pair assisted hydrogen bond. J. Am. Chem. Soc. 2016, 138, 11113−11116.
doi: 10.1021/jacs.6b06312
Liu, Q. Y.; Xiong, W. L.; Liu, C. M.; Wang, Y. L.; Wei, J. J.; Xiahou, Z. J.; Xiong, L. H. Chiral induction in the ionothermal synthesis of a 3D chiral heterometallic metal-organic framework constructed from achiral 1, 4-naphthalenedicarboxylate. Inorg. Chem. 2013, 52, 6773−6775.
doi: 10.1021/ic400853r
Gao, E. Q.; Yue, Y. F.; Bai, S. Q.; He, Z.; Yan, C. H. From achiral ligands to chiral coordination polymers: spontaneous resolution, weak ferromagnetism, and topological ferrimagnetism. J. Am. Chem. Soc. 2004, 126, 1419−1429.
doi: 10.1021/ja039104a
Xue, Z. Z.; Zhang, H.; Sheng, T. L.; Wen, Y. H.; Wang, Y.; Hu, S. M.; Li, H. R.; Zhuo, C.; Wu, X. T. Two chiral coordination polymers constructed from (1R, 2R)-1, 2-diaminocyclohexane derivative: syntheses, structures and properties. Inorg. Chem. Commun. 2015, 55, 99−102.
doi: 10.1016/j.inoche.2015.03.024
Zhang, K.; Jin, C.; Sun, Y. C.; Chang, F. F.; Huang, W. Base-induced self-assembly for one-dimensional coordination polymers via chiral pendant-armed Schiff base mononuclear Pb(Ⅱ) macrocycles. Inorg. Chem. 2014, 53, 7803−7805.
doi: 10.1021/ic5008846
Yadav, M.; Bhunia, A.; Jana, S. K.; Roesky, P. W. Manganese and lanthanide-based 1D chiral coordination polymers as an enantioselective catalyst for sulfoxidation. Inorg. Chem. 2016, 55, 2701−2708.
doi: 10.1021/acs.inorgchem.5b02234
Lewis, K. G.; Ghosh, S. K.; Bhuvanesh, N.; Gladysz, J. A. Cobalt(Ⅲ) Werner complexes with 1, 2-diphenylethylenediamine ligands: readily available, inexpensive, and modular chiral hydrogen bond donor catalysts for enantioselective organic synthesis. ACS Cent. Sci. 2015, 1, 50−56.
doi: 10.1021/acscentsci.5b00035
Davis, K. J.; Richardson, C.; Beck, J. L.; Knowles, B. M.; Guédin, A.; Mergny, J. L.; Willisd, A. C.; Ralph, S. F. Synthesis and characterization of nickel Schiff base complexes containing the meso-1, 2-diphenylethylenediamine moiety: selective interactions with a tetramolecular DNA quadruplex. Dalton Trans. 2015, 44, 3136−3150.
doi: 10.1039/C4DT02926G
Yao, M. X.; Zheng, Q.; Cai, X. M.; Li, Y. Z.; Song, Y.; Zuo, J. L. Chiral cyanide-bridged CrⅢ-MnⅢ heterobimetallic chains based on [(Tp)Cr(CN)3]−: synthesis, structures, and magnetic properties. Inorg. Chem. 2012, 51, 2140−2149.
doi: 10.1021/ic201982d
Margeat, O.; Lacroix, P. G.; Costes, J. P.; Donnadieu, B.; Lepetit, C.; Nakatani, K. Synthesis, structures, and physical properties of copper(Ⅱ)-gadolinium(Ⅲ) complexes combining ferromagnetic coupling and quadratic nonlinear optical properties. Inorg. Chem. 2004, 43, 4743−4750.
doi: 10.1021/ic049801j
Bania, K. K.; Karunakar, G. V.; Goutham, K.; Deka, R. C. Enantioselective henry reaction catalyzed by "ship in a bottle" complexes. Inorg. Chem. 2013, 52, 8017−8029.
doi: 10.1021/ic400599c
Chang, C. W.; Yang, C. T.; Hwang, C. D.; Uang, B. J. 1, 2-Diphenylethylenediamine linked chiral Ti(Ⅳ) complex−a new entry to the highly enantioselective silylcyanation of aliphatic and aromatic aldehydes. Chem. Comm. 2002, 54−55.
Li, X.; Chen, W.; Hems, W.; King, F.; Xiao, J. Asymmetric hydrogenation of ketones with polymer-supported chiral 1, 2-diphenylethylenediamine. Org. Lett. 2003, 5, 4559−4561.
doi: 10.1021/ol0355837
Sterk, D.; Stephan, M. S.; Mohar, B. Transfer hydrogenation of activated ketones using novel chiral Ru(Ⅱ)-N-arenesulfonyl-1, 2-diphenylethylenediamine complexes. Tetrahedron Lett. 2004, 45, 535−537.
doi: 10.1016/j.tetlet.2003.10.201
Chen, G. J.; Wang, J. S.; Jin, F. Z.; Liu, M. Y.; Zhao, C. W.; Li, Y. A.; Dong, Y. B. Pd@Cu(Ⅱ)-MOF-catalyzed aerobic oxidation of benzylic alcohols in air with high conversion and selectivity. Inorg. Chem. 2016, 55, 3058−3064.
doi: 10.1021/acs.inorgchem.5b02973
Sui, Y.; Li, D. P.; Li, C. H.; Zhou, X. H.; Wu, T.; You, X. Z. Ionic ferroelectrics based on nickel Schiff base complexes. Inorg. Chem. 2010, 49, 1286−1288.
doi: 10.1021/ic902136f
Wang, J. S.; Jin, F. Z.; Ma, H. C.; Li, X. B.; Liu, M. Y.; Kan, J. L.; Chen, G. J.; Dong, Y. B. Au@Cu(Ⅱ)-MOF: highly efficient bifunctional heterogeneous catalyst for successive oxidation-condensation reactions. Inorg. Chem. 2016, 55, 6685−6691.
doi: 10.1021/acs.inorgchem.6b00925
Sheldrick, G. M. SHELXS 97, Program for the Solution of Crystal Structures. University of Götingen, Germany 1997.
Sheldrick, G. M. SHELXL 97, Program for the Refinement of Crystal Structures. University of Götingen, Germany 1997.
Addison, A. W.; Rao, T. N.; Reedijk, J.; Rijn, J.; Verschoor, G. C. Synthesis, structure, and spectroscopic properties of copper(Ⅱ) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1, 7-bis(N-methylbenzimidazol-2΄-yl)-2, 6-dithiaheptane]copper(Ⅱ) perchlorate. J. Chem. Soc., Dalton Trans. 1984, 7, 1349−1356.
Liao, W. Q.; Zhou, Q. Q.; Zhang, Y.; Jin, L. Synthesis, structures and dielectric properties of two five-coordinate copper(Ⅱ) complexes based on N-chloromethyl-1, 4-diazabicyclo[2.2.2]octane. Inorg. Chem. Commun. 2013, 33, 161−164.
doi: 10.1016/j.inoche.2013.04.031
Downing, R. S.; Urbach, F. L. The circular dichroism of square-planar, tetradentate Schiff base chelates of copper(Ⅱ). J. Am. Chem. Soc. 1969, 91, 5977−5983.
doi: 10.1021/ja01050a009
Zhang, Y. L.; Gao, F.; Ruan, W. J.; Zhu, Z. A.; Chen, Y. T. Synthesis characterization and CD spectra studies of chiral calixsalen complexes. Chin. J. Chem. 2001, 19, 1296−1301.
Szłyk, E.; Barwiołek, M.; Kruszynski, R.; Bartczak, T. J. Synthesis and spectroscopic studies of the optically active copper(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) complexes with Schiff bases N, N΄-(1R, 2R)(-)-1, 2-cyclohexylenebis(3-methoxybenzylidene-iminato), N, N΄-(1R, 2R)(-)-1, 2-cyclohexylenebis(5-methoxybenzylideneiminato) and X-ray diffraction structure of the [Cu(Ⅱ)(1R, 2R)(-)chxnbis(5-methylbenzylideneiminato)2]. Inorg. Chim. Acta 2005, 358, 3642–3652.
doi: 10.1016/j.ica.2005.06.032
Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
Jiayu Huang , Kuan Chang , Qi Liu , Yameng Xie , Zhijia Song , Zhiping Zheng , Qin Kuang . Fe-N-C nanostick derived from 1D Fe-ZIFs for Electrocatalytic oxygen reduction. Chinese Journal of Structural Chemistry, 2023, 42(10): 100097-100097. doi: 10.1016/j.cjsc.2023.100097
Huan Hu , Ying Zhang , Shi-Shuang Huang , Zhi-Gang Li , Yungui Liu , Rui Feng , Wei Li . Temperature- and pressure-responsive photoluminescence in a 1D hybrid lead halide. Chinese Journal of Structural Chemistry, 2024, 43(10): 100395-100395. doi: 10.1016/j.cjsc.2024.100395
Xudong Zhao , Yuxuan Wang , Xinxin Gao , Xinli Gao , Meihua Wang , Hongliang Huang , Baosheng Liu . Anchoring thiol-rich traps in 1D channel wall of metal-organic framework for efficient removal of mercury ions. Chinese Chemical Letters, 2025, 36(2): 109901-. doi: 10.1016/j.cclet.2024.109901
Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
Wenying Cui , Zhetong Jin , Wentao Fu , Chengshuo Shen . Flag-hinge-like highly luminescent chiral nanographenes with twist geometry. Chinese Chemical Letters, 2024, 35(11): 109667-. doi: 10.1016/j.cclet.2024.109667
Genlin Sun , Yachun Luo , Zhihong Yan , Hongdeng Qiu , Weiyang Tang . Chiral metal-organic frameworks-based materials for chromatographic enantioseparation. Chinese Chemical Letters, 2024, 35(12): 109787-. doi: 10.1016/j.cclet.2024.109787
Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
Chuang LIU , Lichao SUN , Qingfeng ZHANG . Chiral inorganic nanocatalysts for electrochemical and enzyme-mimicked biosensing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 59-78. doi: 10.11862/CJIC.20240406
Cong Gao , Zijian Zhu , Siwei Li , Zheng Xi , Qingqing Sun , Jie Han , Rong Guo . Chiral supramolecular catalysts of helical nanoribbon: More twist, higher enantioselectivity. Chinese Chemical Letters, 2025, 36(3): 109968-. doi: 10.1016/j.cclet.2024.109968
Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
Huiju Cao , Lei Shi . sp1-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
Zhao-Xia Lian , Xue-Zhi Wang , Chuang-Wei Zhou , Jiayu Li , Ming-De Li , Xiao-Ping Zhou , Dan Li . Producing circularly polarized luminescence by radiative energy transfer from achiral metal-organic cage to chiral organic molecules. Chinese Chemical Letters, 2024, 35(8): 109063-. doi: 10.1016/j.cclet.2023.109063
Yongjing Deng , Feiyang Li , Zijian Zhou , Mengzhu Wang , Yongkang Zhu , Jianwei Zhao , Shujuan Liu , Qiang Zhao . Chiral induction and Sb3+ doping in indium halides to trigger second harmonic generation and circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(8): 109085-. doi: 10.1016/j.cclet.2023.109085
Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
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