Citation: Lu LIU, Abaid Ullah Malik, Mou-Hai SHU. Syntheses, Crystal Structures and Fluorescence Properties of Four Coordination Polymers Based on Enantiomeric 2-(4-Carboxyphenyl)-4, 5-dihydrothiazole-4-carboxylic Acid Ligands[J]. Chinese Journal of Structural Chemistry, ;2020, 39(3): 567-578. doi: 10.14102/j.cnki.0254-5861.2011-2515 shu

Syntheses, Crystal Structures and Fluorescence Properties of Four Coordination Polymers Based on Enantiomeric 2-(4-Carboxyphenyl)-4, 5-dihydrothiazole-4-carboxylic Acid Ligands

School of Chemistry and Chemical Engineering, Shanghai Jiaotong University, Shanghai 200240, China

Corresponding author: Mou-Hai SHU, mhshu@sjtu.edu.cn
Received Date: 27 May 2019
Accepted Date: 20 June 2019

Fund Project: the National Natural Science Foundation of China 21271129

Figures(10)

A pair of enatiomerically pure ligands, (R-)/(S-)2-(4-carboxyphenyl)-4, 5-dihydrothiazole-4-carboxylic acid (H₂L^R & H₂L^S), have been synthesized by the reactions of 4-cyanobenzoic acid with L- and D-cysteine, respectively. Four coordination polymers have been prepared from the ligands and structurally determined by single-crystal X-ray diffraction analysis. Complexes 1R and 1S ([NiL(Py)(H₂O)]⋅H₂O, for 1R, L = (L^R)^2-; for 1S, L = (L^S)^2-) exhibit chiral helical one-dimensional chains, and complexes 2R and 2S ({[ZnL₂(H₂O)₃]⋅CH₃CN}_n, for 2R L = (L^R)^2-, for 2S L = (L^S)^2-) are two-dimensional sheets. Luminescent and chir-optical properties have been investigated and compared with the free ligands. The complexes have blue-shift in luminescence spectrum compared with the free ligands.
- coordination polymer,
- crystal structure,
- chiral ligand,
- fluorescence
1. [1]
  Morris, R. E.; Bu, X. Induction of chiral porous solids containing only achiral building blocks. Nat. Chem. 2010, 2, 353-361. doi: 10.1038/nchem.628
2. [2]
  Kaczorowski, T.; Justyniak, I.; Lipińska, T.; Lipkowski, J.; Lewiński, J. Metal complexes of cinchonine as chiral building blocks: a strategy for the construction of nanotubular architectures and helical coordination polymers. J. Am. Chem. Soc. 2009, 131, 5393-5395. doi: 10.1021/ja8098867
3. [3]
  Meng, C. L.; Li, Z. J.; Liu, Y.; Liu, B. Z.; Cui, Y. Synthesis, structure and characterization of a 3D chiral indium carboxylate metal-organic framework based on 1, 1΄-biphenol ligand. Chin. J. Struct. Chem. 2017, 36, 2081-2086.
4. [4]
  Zhang, F. W.; Zhou, Y. F.; Dong, J. Q.; Liu, B. Z.; Zheng, S. J.; Cui, Y. Synthesis and crystal structure of a novel chiral 3D metal-organic framework based on an N-methyl substituted salan ligand. Chin. J. Struct. Chem. 2014, 33, 1154-1158.
5. [5]
  Jiao, J. J.; Li, Z. J.; Zheng, F. K.; Liu, B. Z.; Cui, Y. Synthesis, structure and characterization of a 3D chiral carboxylate and phosphonate metalorganic framework based on 1, 1΄-biphenol ligand. Chin. J. Struct. Chem. 2018, 37, 1509-1515.
6. [6]
  Yoon, M.; Srirambalaji, R.; Kim, K. Homochiral metal-organic frameworks for asymmetric heterogeneous catalysis. Chem. Rev. 2012, 112, 1196-2310. doi: 10.1021/cr2003147
7. [7]
  Xia, Q.; Li, Z.; Tan, C.; Liu, Y.; Gong, W.; Cui, Y. Multivariate metal-organic frameworks as multifunctional heterogeneous asymmetric catalysts for sequential reactions. J. Am. Chem. Soc. 2017, 139, 8259–8266. doi: 10.1021/jacs.7b03113
8. [8]
  Ma, L.; Falkowski, J.; Abney, C.; Lin, W. A series of isoreticular chiral metal-organic frameworks as a tunable platform for asymmetric catalysis. Nat. Chem. 2010, 2, 838–846. doi: 10.1038/nchem.738
9. [9]
  Falkowski, J. M.; Sawano, T.; Zhang, T.; Tsun, G.; Chen, Y.; Lockard, J. V.; Lin, W. Privileged phosphine-based metal-organic frameworks for broad-scope asymmetric catalysis. J. Am. Chem. Soc. 2014, 136, 5213–5216. doi: 10.1021/ja500090y
10. [10]
  Dang, D.; Wu, P.; He, C.; Xie, Z.; Duan, C. Homochiral metal-organic frameworks for heterogeneous asymmetric catalysis. J. Am. Chem. Soc. 2010, 132, 14321–14323. doi: 10.1021/ja101208s
11. [11]
  Ye, C.; Zhu, C.; Gong, T.; Shen, E.; Xuan, W.; Cui, Y.; Liu, B. A novel Cu-based metallosalan complex: synthesis, structure and chiral sensor study. Chin. J. Struct. Chem. 2013, 32, 1076–1082.
12. [12]
  Wanderley, M.; Wang, C.; Wu, C.; Lin, W. A chiral porous metal-organic framework for highly sensitive and enantioselective fluorescence sensing of amino alcohols. J. Am. Chem. Soc. 2012, 134, 9050–9053. doi: 10.1021/ja302110d
13. [13]
  Peluso, P.; Mamane, V.; Cossu, S. Homochiral metal-organic frameworks and their application in chromatography enantioseparations. J. Chromatogr. A 2014, 1363, 11–26. doi: 10.1016/j.chroma.2014.06.064
14. [14]
  Yang, X. L.; Wu, C. D. Recent advances on porous homochiral coordination polymers containing amino acid synthons. CrystEngComm. 2014, 16, 4907–4918. doi: 10.1039/C3CE42508H
15. [15]
  Chen, L.; Kang, J.; Cui, H.; Wang, Y.; Liu, L.; Zhang, L.; Su, C. Y. Homochiral coordination cages assembled from dinuclear paddlewheel nodes and enantiopure ditopic ligands: syntheses, structures and catalysis. Dalton Trans. 2015, 44, 12180–12188. doi: 10.1039/C4DT03782K
16. [16]
  Yoon, T. P.; Jacobsen, E. N. Privileged chiral catalysts. Science 2003, 299, 1691–1693. doi: 10.1126/science.1083622
17. [17]
  Zhou, Q. L. Privileged Chiral Ligands and Catalysts. John Wiley & Sons 2011.
18. [18]
  Li, J. B.; Wang, Q.; Liu, H. W.; Yin, X.; Hu, X. X.; Yuan, L.; Zhang, X. B. Engineering of a bioluminescent probe for imaging nitroxyl in live cells and mice. Chem. Commun. 2019, 55, 1758–1761. doi: 10.1039/C9CC00211A
19. [19]
  Takakura, H.; Kojima, R.; Kamiya, M.; Kobayashi, E.; Komatsu, T.; Ueno, T.; Terai, T.; Hanaoka, K.; Nagano, T.; Urano, Y. New class of bioluminogenic probe based on bioluminescent enzyme-induced electron transfer: BioLeT. J. Am. Chem. Soc. 2015, 137, 4010–4013. doi: 10.1021/ja511014w
20. [20]
  Zhou, X. L.; Shu, M. H. Syntheses, crystal structures and fluorescence properties of two complexes based on a new chiral ligand. Chin. J. Struct. Chem. 2017, 36, 1518-1525.
21. [21]
  Malik, A. U.; Zhou, X. L.; Kong, S. N.; Li, L. L; Bao, X. L.; Shu, M. H. Homochiral hexanuclear nickel(Ⅱ) metallocyclic structures with high activity for the photocatalytic degradation of organic dyes. Dalton Trans. 2018, 47, 1764–1767. doi: 10.1039/C7DT04436D
22. [22]
  Sheldrick, G. M. SHELXT-Integrated space-group and crystal structure determination. Acta Crystallogr. A 2015, 71, 3–8. doi: 10.1107/S2053273314026370
23. [23]
  Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. C 2015, 71, 3–8. doi: 10.1107/S2053229614024218
24. [24]
  Addison, A. W.; Rao, T. N.; Reedijk, J.; van 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, 1349–1356.
25. [25]
  Zhang, H.; Jiang, W.; Yang, J.; Liu, Y. Y.; Song, S.; Ma, J. F. Four coordination polymers constructed by a novel octacarboxylate functionalized calix[4]arene ligand: syntheses, structures, and photoluminescence property. CrystEngComm. 2014, 16, 9939–9946. doi: 10.1039/C4CE01581A
26. [26]
  Zavakhina, M. S.; Samsonenko, D. G.; Dybtsev, D. N.; Fedin, V. P. Chiral MOF incorporating chiral guests: structural studies and enantiomer-dependent luminescent properties. Polyhedron 2019, 162, 311–315. doi: 10.1016/j.poly.2019.02.008
27. [27]
  Kan, W. Q.; Liu, B.; Yang, J.; Liu, Y. Y.; Ma, J. F. A series of highly connected metal-organic frameworks based on triangular ligands and d10 metals: syntheses, structures, photoluminescence, and photocatalysis. Cryst. Growth Des. 2012, 12, 2288–2298. doi: 10.1021/cg2015644
1. [1]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
2. [2]
  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
3. [3]
  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
4. [4]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
5. [5]
  Jing REN , Ruikui YAN , Xiaoli CHEN , Huali CUI , Hua YANG , Jijiang WANG . Synthesis and fluorescence sensing of a highly sensitive and multi-response cadmium coordination polymer. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 574-586. doi: 10.11862/CJIC.20240287
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
10. [10]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
11. [11]
  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
12. [12]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
13. [13]
  Qingyan JIANG , Yanyong SHA , Chen CHEN , Xiaojuan CHEN , Wenlong LIU , Hao HUANG , Hongjiang LIU , Qi LIU . Constructing a one-dimensional Cu-coordination polymer-based cathode material for Li-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 657-668. doi: 10.11862/CJIC.20240004
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(335)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142