Citation: Chen Zhonghang, Han Zongsu, Shi Wei, Cheng Peng. Design, Synthesis and Applications of Chiral Metal-Organic Frameworks[J]. Acta Chimica Sinica, ;2020, 78(12): 1336-1348. doi: 10.6023/A20090439 shu

Design, Synthesis and Applications of Chiral Metal-Organic Frameworks

College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Shi Wei, shiwei@nankai.edu.cn
Received Date: 23 September 2020
Available Online: 9 December 2020
Fund Project: the Fundamental Research Funds for the Central Universities, Nankai University 63201043the Fundamental Research Funds for the Central Universities, Nankai University 63201016the Natural Science Foundation of Tianjin 18JCJQJC47200Project supported by the National Natural Science Foundation of China (No. 21861130354), the Natural Science Foundation of Tianjin (No. 18JCJQJC47200) and the Fundamental Research Funds for the Central Universities, Nankai University (Nos. 63201016, 63201043)the National Natural Science Foundation of China 21861130354

Figures(12)

Chiral metal-organic frameworks have shown important applications in the identification and separation of enantiomers and asymmetric heterogeneous catalysis, owing to their structural diversities and multifunctionalities. Recently, the applications of chiral metal-organic frameworks have been expanded to other research fields, such as circularly polarized luminescence and chiral ferroelectrics. Compared with achiral metal-organic frameworks, it is highly challenging to synthesize chiral metal-organic frameworks, because the chirality introduction usually results in the difficulty of the crystallization and purification process for the design of chiral metal-organic frameworks. In this review, we discussed three main strategies that have been utilized to construct chiral metal-organic frameworks, including direct synthesis by chiral ligands, spontaneous resolution with achiral ligands or in the presence of chiral-template, and post-synthetic modification of achiral metal-organic frameworks. Moreover, the recent research progresses of chiral metal-organic frameworks in chiral molecular recognition, enantiomer separation, asymmetric catalysis, circularly polarized luminescence, and chiral ferroelectrics are discussed.
- chirality,
- metal-organic frameworks,
- design and synthesis,
- property
1. [1]
  Lin, G.-Q.; Sun, X.-W.; Hong, R. Chiral Synthesis: Basic Research and Progress, Science Press, Beijing, 2018 (in Chinese).
2. [2]
  Wang, Y.; Xu, J.; Wang, Y. W.; Chen, H. Y. Chem. Soc. Rev. 2013, 42, 2930.
3. [3]
  Zhao, K.-H.; Zhong, X.-H. Optics, Peking University Press, Beijing, 2018 (in Chinese).
4. [4]
  You, Q.-D.; Lin, G.-Q. Chiral Drugs: Research and Evaluation, Chemical Industry Press, Beijing, 2011 (in Chinese).
5. [5]
  Zhou, Q. L. Privileged Chiral Ligands and Catalysts, Wiley-VCH, 2011.
6. [6]
  Zhang, L.; Qin, L.; Wang, X.; Cao, H.; Liu, M. Adv. Mater. 2014, 26, 6959.
7. [7]
  Constable, E. C.; Housecroft, C. E. Chem. Soc. Rev. 2013, 42, 1429.
8. [8]
  Furukawa, H.; Cordova, K. E.; O'Keeffe, M.; Yaghi, O. M. Science 2013, 341, 1230444.
9. [9]
  Chen, X.-M.; Zhang, J.-P. et al., Metal-Organic Frameworks, Chemical Industry Press, Beijing, 2017 (in Chinese).
10. [10]
  Bloch, E. D.; Queen, W. L.; Krishna, R.; Zadrozny, J. M.; Brown, C. M.; Long, J. R. Science 2012, 335, 1606.
11. [11]
  Wu, S. Y.; Min, H.; Shi, W.; Cheng, P. Adv. Mater. 2020, 32, 1805871.
12. [12]
  Zhu, L.; Liu, X. Q.; Jiang, H. L.; Sun, L. B. Chem. Rev. 2017, 117, 8129.
13. [13]
  Cai, G.; Ding, M.; Wu, Q.; Jiang, H.-L. Natl. Sci. Rev. 2020, 7, 37.
14. [14]
  Pan, Y.; Qian, Y.; Zheng, X.; Chu, S.-Q.; Yang, Y.; Ding, C.; Wang, X.; Yu, S.-H.; Jiang, H.-L. Natl. Sci. Rev. 2020, doi: 10.1093/nsr/nwaa224. doi: 10.1093/nsr/nwaa224.
15. [15]
  Huang, G.; Chen, Y.-Z.; Jiang, H.-L. Acta Chim. Sinica 2016, 74, 113 (in Chinese).
16. [16]
  Wu, Q.-Y.; Zhang, C.-X.; Sun, K.; Jiang, H.-L. Acta Chim. Sinica 2020, 78, 688 (in Chinese).
17. [17]
  Batten, S. R.; Champness, N. R.; Chen, X. M.; Garcia-Martinez, J.; Kitagawa, S.; hrstrm, L.; O’Keeffe, M.; Suh, M. P.; Reedijk, J. Pure Appl. Chem. 2013, 85, 1715.
18. [18]
  Yaghi, O. M.; Kalmutzki, M. J.; Diercks, C. S. Introduction to Reticular Chemistry: Metal-Organic Frameworks and Covalent Organic Frameworks, Wiley-VCH, Weinheim, 2019.
19. [19]
  Zhao, X.; Wang, Y. X.; Li, D. S.; Bu, X. H.; Feng, P. Y. Adv. Mater. 2018, 30, 1705189.
20. [20]
  Li, X.; Wu, J.; He, C.; Meng, Q.; Duan, C. Small 2019, 15, 1970171.
21. [21]
  Ma, L. Q.; Abney, C.; Lin, W. B. Chem. Soc. Rev. 2009, 38, 1248.
22. [22]
  Liu, Y.; Xuan, W. M.; Cui, Y. Adv. Mater. 2010, 22, 4112.
23. [23]
  Morris, R. E.; Bu, X. H. Nature Chem. 2010, 2, 353.
24. [24]
  Yoon, M.; Srirambalaji, R.; Kim, K. Chem. Rev. 2012, 112, 1196.
25. [25]
  Gu, Z. G.; Zhan, C. H.; Zhang, J.; Bu, X. H. Chem. Soc. Rev. 2016, 45, 3122.
26. [26]
  Han, Z. S.; Shi, W.; Cheng, P. Chin. Chem. Lett. 2018, 29, 819.
27. [27]
  Liu, Y.; Li, W.; Zhang, J. Natl. Sci. Rev. 2017, 4, 326.
28. [28]
  Zhao, X.; Nguyen, E. T.; Hong, A. N.; Feng, P.; Bu, X. Angew. Chem. Int. Ed. 2018, 57, 7101.
29. [29]
  梅佩, 张媛媛, 冯霄, 化学学报, 2020, 78, 1041.
30. [30]
  Corella-Ochoa, M. N.; Tapia, J. B.; Rubin, H. N.; Lillo, V.; González-Cobos, J. J. Am. Chem. Soc. 2019, 141, 14306.
31. [31]
  Vaidhyanathan, R.; Bradshaw, D.; Rebilly, J.-N.; Barrio, J.-P.; Gould, J.-A.; Berry, N.-G.; Rosseinsky, M.-J. Angew. Chem. Int. Ed. 2006, 45, 6495.
32. [32]
  Cai, H.; Huang, Y.-L.; Li, D. Coord. Chem. Rev. 2019, 378, 207.
33. [33]
  Xu, Z. X.; Liu, L.; Zhang, J. Inorg. Chem. 2016, 55, 6355.
34. [34]
  Liu, J.; Wang, F.; Zhang, J. Cryst. Growth Des. 2017, 17, 5393.
35. [35]
  Zhang, S. Y.; Yang, C. X.; Shi, W.; Yan, X.-P.; Cheng, P.; Wojtas, L.; Zaworotko, M. J. Chem 2017, 3, 281.
36. [36]
  Wanderley, M. M.; Wang, C.; Wu, C. D.; Lin, W. J. Am. Chem. Soc. 2012, 134, 9050.
37. [37]
  Cortijo, M.; Valentín-Pérez, .; Rouzières, M.; Clérac, R.; Rosa, P.; Hillard, E. A. Crystals 2020, 10, 472.
38. [38]
  Zhang, X.; Xu, N.; Zhang, S.-Y.; Zhao, X.-Q.; Cheng, P. RSC Adv. 2014, 4, 40643.
39. [39]
  Wen, Q.; Tenenholtz, S.; Shimon, L.; Omri, B.-E.; Beck, L. M.; Houben, L.; Cohen, S. R.; Feldman, Y.; Oron, D.; Lahav, M.; Boom, M. E. J. Am. Chem. Soc. 2020, 142, 14210.
40. [40]
  Zuo, T.; Luo, D.; Huang, Y. L.; Li, Y. Y.; Zhou, X. P.; Li, D. Chem. Eur. J. 2020, 26, 1936.
41. [41]
  Han, Y.-H.; Liu, Y.-C.; Xing, X.-S.; Tian, C.-B.; Lin, P.; Du, S.-W. Chem. Commun. 2015, 51, 14481.
42. [42]
  Das, S.; Xu, S.; Ben, T.; Qiu, S. Angew. Chem. Int. Ed. 2018, 57, 8629.
43. [43]
  Kou, W.-T.; Yang, C.-X.; Yan, X.-P. J. Mater. Chem. A 2018, 6, 17861.
44. [44]
  Lu, Y.; Zhang, H.; Chan, J. Y.; Ou, R.; Zhu, H.; Forsyth, M.; Marijanovic, E. M.; Doherty, C. M.; Marriott, P. J.; Banaszak Holl, M. M.; Wang, H. Angew. Chem. Int. Ed. 2019, 131, 17084.
45. [45]
  Tan, C.; Han, X.; Li, Z.; Liu, Y.; Cui, Y. J. Am. Chem. Soc. 2018, 140, 16229.
46. [46]
  Han, Z.; Wang, K.; Guo, Y.; Chen, W.; Zhang, J.; Zhang, X.; Siligardi, G.; Yang, S.; Zhou, Z.; Sun, P.; Shi, W.; Cheng, P. Nat. Commun. 2019, 10, 5117.
47. [47]
  Zhao, Y. W.; Zhang, X. M. J. Mater. Chem. C 2020, 8, 4453.
48. [48]
  Zhao, Y. W.; Wang, Y.; Zhang, X. M. ACS Appl. Mater. Interfaces 2017, 9, 20991.
49. [49]
  Franks, M. E.; Macpherson, G. R.; Figg, W. D. The Lancet 2004, 363, 1802.
50. [50]
  Abbas, A.; Wang, Z.-X.; Li, Z.; Jiang, H.; Liu, Y.; Cui, Y. Inorg. Chem. 2018, 57, 8697.
51. [51]
  Xie, S. M.; Zhang, Z. J.; Wang, Z. Y.; Yuan, L. M. J. Am. Chem. Soc. 2011, 133, 11892.
52. [52]
  José, N.-S.; Ana, A.-G.; Yolanda, M.-M.; Ganiel, R.-S.; Antypov, D.; Pilar, C.-F.; Rosseinsky, M. J.; Carlos, M.-G. J. Am. Chem. Soc. 2017, 139, 4294.
53. [53]
  Zhao, J.; Li, H.; Han, Y.; Li, R.; Ding, X.; Feng, X.; Wang, B. J. Mater. Chem. A 2015, 3, 12145.
54. [54]
  Chan, J. Y.; Zhang, H.; Nolvachai, Y.; Hu, Y.; Zhu, H.; Forsyth, M.; Gu, Q.; Hoke, D. E.; Zhang, X.; Marriot, P. J.; Wang, H. Angew. Chem. Int. Ed. 2018, 57, 17376.
55. [55]
  Seo, J. S.; Whang. D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982.
56. [56]
  Dang, D.; Wu, P.; He, C.; Xie, Z.; Duan, C. J. Am. Chem. Soc. 2010, 132, 14321.
57. [57]
  Han, Q.; Qi, B.; Ren, W.; He, C.; Niu, J.; Duan, C. Nat. Commun. 2015, 6, 10007.
58. [58]
  Han, Q.; He, C.; Zhao, M.; Qi, B.; Niu, J.; Duan, C. J. Am. Chem. Soc. 2013, 135, 10186.
59. [59]
  Fan, Y.; Ren, Y.; Li, J.; Yue, C.; Jiang, H. Inorg. Chem. 2018, 57, 11986.
60. [60]
  Gong, W.; Chen, X.; Jiang, H.; Chu, D.; Cui, Y.; Liu, Y. J. Am. Chem. Soc. 2019, 141, 7498.
61. [61]
  Jiang, H.; Zhang, W.; Kang, X.; Cao, Z.; Chen, X.; Liu, Y.; Cui, Y. J. Am. Chem. Soc. 2020, 142, 9642.
62. [62]
  Sang, Y.; Han, J.; Zhao, T.; Duan, P.; Liu, M. Adv. Mater. 2020, 32, 1900110.
63. [63]
  Zhao, T.; Han, J.; Duan, P.; Liu, M. Acc. Chem. Res. 2020, 53, 1279.
64. [64]
  Li, M.; Lin, W.-B.; Fang, L.; Chen, C.-F. Acta Chim. Sinica 2017, 75, 1150 (in Chinese).
65. [65]
  Chen, S. M.; Chang, L. M.; Yang, X. K.; Luo, T.; Xu, H.; Gu, Z. G.; Zhang, J. ACS Appl. Mater. Interfaces 2019, 11, 31421.
66. [66]
  Zhao, T.; Han, J.; Jin, X.; Liu, Y.; Liu, M.; Duan, P. Angew. Chem. Int. Ed. 2019, 58, 4978.
67. [67]
  Zhao, T.; Han, J.; Jin, X.; Zhou, M.; Liu, Y.; Duan, P.; Liu, M. Research 2020, doi: 10.34133/2020/6452123. doi: 10.34133/2020/6452123.
68. [68]
  Hu, L.; Li, K.; Shang, W.; Zhu, X.; Liu, M. Angew. Chem. Int. Ed. 2020, 59, 4953.
69. [69]
  Shang, W.; Zhu, X.; Liang, T.; Du, C.; Hu, L.; Li, T.; Liu, M. Angew. Chem. Int. Ed. 2020, 59, 12811.
70. [70]
  Shi, P.-P.; Tang, Y.-Y.; Li, P.-F.; Liao, W.-Q.; Wang, Z.-X.; Ye, Q.; Xiong, R.-G. Chem. Soc. Rev. 2016, 45, 3811.
71. [71]
  Guo, Z.; Cao, R.; Wang, X.; Li, H.; Yuan, W.; Wang, G.; Wu, H.; Li, J. J. Am. Chem. Soc. 2009, 131, 6894.
72. [72]
  Dong, X. Y.; Li, B.; Ma, B. B.; Li, S. J.; Dong, M. M.; Zhu, Y. Y.; Zang, S. Q.; Song, Y.; Hou, H. W.; Mak, T. C. J. Am. Chem. Soc. 2013, 135, 10214.
73. [73]
  Mon, M.; Ferrando-Soria, J.; Verdaguer, M.; Train, C.; Paillard, C.; Dkhil, B.; Versace, C.; Bruno, R.; Armentano, D.; Pardo, E. J. Am. Chem. Soc. 2017, 139, 8098.
1. [1]
  Simin Fang , Hong Wu , Sizhe Sheng , Lingling Li , Yuxi Wang , Hongchun Li , Jun Jiang . The Food Kingdom Lecture Series: The Science behind Color. University Chemistry, 2024, 39(9): 177-182. doi: 10.12461/PKU.DXHX202402012
2. [2]
  Laiying Zhang , Yaxian Zhu . Exploring the Silver Family. University Chemistry, 2024, 39(9): 1-4. doi: 10.12461/PKU.DXHX202409015
3. [3]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
4. [4]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
5. [5]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
6. [6]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
7. [7]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
8. [8]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
9. [9]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
10. [10]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
11. [11]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
12. [12]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
13. [13]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
14. [14]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
15. [15]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
16. [16]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
17. [17]
  Xuan Zhou , Yi Fan , Zhuoqi Jiang , Zhipeng Li , Guowen Yuan , Laiying Zhang , Xu Hou . Liquid Gating Mechanism and Basic Properties Characterization: a New Experimental Design for Interface and Surface Properties in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 113-120. doi: 10.12461/PKU.DXHX202407111
18. [18]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
19. [19]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
20. [20]
  Yuan Zheng , Quan Lan , Zhenggen Zha , Lingling Li , Jun Jiang , Pingping Zhu . Teaching Reform of Organic Synthesis Experiments by Introducing Reverse Thinking and Design Concepts: Taking the Synthesis of Cinnamic Acid Based on Retrosynthetic Analysis as an Example. University Chemistry, 2024, 39(6): 207-213. doi: 10.3866/PKU.DXHX202310065

Get Citation

PDF

XML

Metrics

PDF Downloads(224)
Abstract views(6415)
HTML views(1723)

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