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Synthesis and Application of Chiral Organic Imine Molecular Cages

  • Luyi Chen ,
  • Mengxia Tan ,
  • Jia'nan Jin ,
  • Zibin Zhang ,
  • Feihe Huang ,
  • Shijun Li ,
  • Yunxia Li
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  • a College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121
    b Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310058
    c Zhejiang-Israel Joint Laboratory of Self-Assembling Functional Materials, ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311215

Received date: 2024-01-12

  Revised date: 2024-03-18

  Online published: 2024-04-10

Supported by

National Natural Science Foundation of China(21773052); National Natural Science Foundation of China(22071040); Natural Science Foundation of Zhejiang Province(LZ24B020005)

Abstract

As a kind of novel porous materials, porous organic molecular cages (POCs) exhibit excellent properties in the field of molecular recognition, gas storage and separation, catalysis and sensing. Moreover, their good solubilities make them easily fabricate composite materials to obtain more complicated structures and interesting performances. As one of main family members of POCs, organic imine molecular cages based on dynamic imine bonds have been extensively studied. Among them, chiral organic imine molecular cages have exhibited the wide applications of POCs in the fields such as chiral recognition, enantiomer separation, asymmetric catalysis, and so on. In order to provide a comprehensive overview of the synthesis and applications of chiral organic imine molecular cages, three effective synthetic strategies of chiral organic imine molecular cages, including direct synthesis by using enantiopure chiral building blocks, chiral assembly with achiral building blocks under the effect of symmetry breaking, and chiral self-sorting assembly with racemic building blocks, are summarized. The recent progresses of the applications of chiral organic molecular imine cages in the fields of chiral molecular recognition, chiral chromatographic separation and asymmetric catalysis are also briefly retrospected.

Cite this article

Luyi Chen , Mengxia Tan , Jia'nan Jin , Zibin Zhang , Feihe Huang , Shijun Li , Yunxia Li . Synthesis and Application of Chiral Organic Imine Molecular Cages[J]. Chinese Journal of Organic Chemistry, 2024 , 44(9) : 2617 -2639 . DOI: 10.6023/cjoc202401011

References

[1]
Sun, Z. F.; Hou, J. J.; Li, L. S.; Tang, Z. Y. Coord. Chem. Rev. 2020, 425, 213481.
[2]
Zhuo, S. Q.; Zhang, X. Y.; Luo, H.; Wang, X. H.; Ji, Y. B. Macromol. Rapid. Commun. 2020, 41, 2000404.
[3]
Zhang, Y.; Jin, X. N.; Ma, X. F.; Wang, Y. Anal. Methods 2021, 13, 8.
[4]
Lu, Y. Z. H.; Zhang, H. C.; Zhu, Y. L.; Marriott, P. J.; Wang, H. T. Adv. Funct. Mater. 2021, 31, 2101335.
[5]
Hasell, T.; Cooper, A. I. Nat. Rev. Mater. 2016, 1, 1.
[6]
Zhang, J. H.; Xie, S. M.; Zi, M.; Yuan, L. M. J. Sep. Sci. 2020, 43, 134.
[7]
Hu, D. Y.; Zhang, J. J.; Liu, M. Chem. Commun. 2022, 58, 11333.
[8]
Montà-González, G.; Sancenón, F.; Martínez-Má?ez, R.; Martí- Centelles, V. Chem. Rev. 2022, 122, 13636.
[9]
Bhandari, P.; Mukherjee, P. S. ACS Catal. 2023, 13, 6126.
[10]
Zhang, G.; Mastalerz, M. ; Chem. Soc. Rev. 2014, 43, 1934.
[11]
Huang, S. L.; Jin, G. X.; Luo, H. K.; Andy Hor, T. S. Chem.-Asian J. 2015, 10, 24.
[12]
Acharyya, K.; Mukherjee, P. S. Angew. Chem., Int. Ed. 2019, 58, 8640.
[13]
Quan, M. L. C.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2754.
[14]
Tozawa, T.; Jones, J. T. A.; Swamy, S. I.; Jiang, S.; Adams, D. J.; Shakespeare, S.; Clowes, R.; Bradshaw, D.; Hasell, T.; Chong, S. Y.; Tang, C.; Thompson, S. ; Parker, J.; Trewin, A.; Bacsa, J.; Slawin, A. M. Z.; Steiner, A.; Cooper, A. I. Nat. Mater. 2009, 8, 973.
[15]
Evans, J. D.; Sumby, C. J.; Doonan, C. J. Chem. Lett. 2015, 44, 582.
[16]
Yu, N.; Ding, H. M.; Wang, C. Prog. Chem. 2016, 28, 1721 (in Chinese).
[16]
(喻娜, 丁慧敏, 汪成, 化学进展, 2016, 28, 1721.)
[17]
Xu, Z. Z.; Ye, Y. Z.; Liu, H. L.; Liu, H. Y.; Jiang, S. Chem. Commun. 2024, 60, 2261.
[18]
Santolini, V.; Miklitz, M.; Berardo, E.; Jelfs, K. E. Nanoscale 2017, 9, 5280.
[19]
Ono, K.; Iwasawa, N. Chem.-Eur. J. 2018, 24, 17856.
[20]
Skowronek, P.; Gawronski, J. Org. Lett. 2008, 10, 4755.
[21]
Jones, J. T. A.; Hasell, T.; Wu, X. F; Bacsa, J.; Jelfs, K. E.; Schmidtmann, M.; Chong, S. Y.; Adams, D. J.; Trewin, A.; Schiffman, F.; Cora, F.; Slater, B.; Steiner, A.; Day, G. M.; Cooper, A. I. Nature 2011, 474, 367.
[22]
Bojdys, M. J.; Briggs, M. E.; Jones, J. T. A.; Adams, D. J.; Chong, S. Y.; Schmidtmann, M.; Cooper, A. I. J. Am. Chem. Soc. 2011, 133, 16566.
[23]
Giri, N.; Davidson, C. E.; Melaugh, G.; Del Pópolo, M. G.; Jones, J. T. A.; Hasell, T.; Cooper, A. I.; Horton, P. N.; Hursthouse, M. B.; James, S. L. Chem. Sci. 2012, 3, 2153.
[24]
Jelfs, K. E.; Wu, X. F.; Schmidtmann, M.; Jones, J. T. A.; Warren, J. E.; Adams, D. J.; Cooper, A. I. Angew. Chem., Int. Ed. 2011, 50, 10653.
[25]
Wang, W. L.; Li, C. Y.; Zhang, H.; Zhang, J. W.; Lu, L. L.; Jiang, Z.; Cui, L. F.; Liu, H. G.; Yan, L.; Ding, Y. J. Chin. J. Catal. 2021, 42, 1216.
[26]
Mondal, B.; Acharyya, K.; Howlader, P.; Mukherjee, P. S. J. Am. Chem. Soc. 2016, 138, 1709.
[27]
Ding, H. M.; Yang, Y. H.; Li, B. J.; Pan, F.; Zhu, G. Z.; Zeller, M.; Yuan, D. Q.; Wang, C. Chem. Commun. 2015, 51, 1976.
[28]
Mondal, B.; Mukherjee, P. S. J. Am. Chem. Soc. 2018, 140, 12592.
[29]
Feng, G. F.; Liu, W.; Peng, Y. X.; Zhao, B.; Huang, W.; Dai, Y. F. Chem. Commun. 2016, 52, 9267.
[30]
Slater, A. G.; Little, M. A.; Pulido, A.; Chong, S. Y.; Holden, D.; Chen, L.; Morgan, C.; Wu, X.; Cheng, G.; Clowes, R.; Briggs, M. E.; Hasell, T.; Jelfs, K. E.; Day, G. M.; Cooper, A. I. Nat. Chem. 2017, 9, 17.
[31]
Sun, N.; Wang, C. M.; Wang, H. L.; Yang, L.; Jin, P.; Zhang, W.; Jiang, J. Z. Angew. Chem., Int. Ed. 2019, 58, 18011.
[32]
Liu, C.; Liu, K. H.; Wang, C. M.; Liu, H. Y.; Wang, H. L.; Su, H. M.; Li, X. Y; Chen, B. L.; Jiang, J. Z. Nat. Commun. 2020, 11, 1047.
[33]
Zhang, L.; Liang, R. R.; Hang, C.; Wang, H. Y.; Sun, L.; Xu, L.; Liu, D. R.; Zhang, Z. Y.; Zhang, X. M.; Chang, F. F.; Zhao, S. Y.; Huang, W. Green Chem. 2020, 22, 2498.
[34]
Lei, Y.; Chen, Q.; Liu, P.; Wang, L. X.; Wang, H. Y.; Li, B. D.; Lu, X. Y.; Chen, Z.; Pan, Y. J.; Huang, F. H.; Li, H. Angew. Chem., Int. Ed. 2021, 60, 4705.
[35]
Bhandari, P.; Mondal, B.; Howlader, P.; Mukherjee, P. S. Eur. J. Inorg. Chem. 2022, 2022, e202100986.
[36]
?olomek, T.; Powers-Riggs, N. E.; Wu, Y. L.; Young, R. M.; Krzyaniak, M. D.; Horwitz, N. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2017, 139, 3348.
[37]
Feng, X. Y.; Liao, P. S.; Jiang, J. X.; Shi, J. Y.; Ke, Z. F.; Zhang, J. Y. ChemPhotoChem 2019, 3, 1014.
[38]
Xu, N.; Su, K. Z.; El-Sayed, E. M.; Ju, Z. F.; Yuan, D. Q. Chem. Sci. 2022, 13, 3582.
[39]
Malik, A. U.; Gan, F. W.; Shen, C. S.; Yu, N.; Wang, R. B.; Crassous, J.; Shu, M. H.; Qiu, H. B. J. Am. Chem. Soc. 2018, 140, 2769.
[40]
Ramakrishna, E.; Tang, J. D.; Tao, J. J.; Fang, Q.; Zhang, Z. B.; Huang, J. Y.; Li, S. J. Chem. Commun. 2021, 57, 9088.
[41]
Liu, C.; Jin, Y. C.; Qi, D. D.; Ding, X. ; Ren, H. M.; Wang, H. L.; Jiang, J. Z. Chem. Sci. 2022, 13, 7014.
[42]
Liu, J. G.; Yin, F.; Hu, J.; Ju, Y. Chin. J. Org. Chem. 2021, 41, 1031 (in Chinese).
[42]
(刘金果, 殷凤, 胡君, 巨勇, 有机化学, 2021, 41, 1031.)
[43]
Wang, X. C.; Wang, Y.; Yang, H. Y.; Fang, H. X.; Chen, R. X.; Sun, Y. B.; Zheng, N. F.; Tan, K.; Lu, X.; Tian, Z. Q.; Cao, X. Y. Nat. Commun. 2016, 7, 12469.
[44]
Qu, H.; Wang, Y.; Li, Z. H.; Wang, X. C.; Fang, H. X.; Tian, Z. Q.; Cao, X. Y. J. Am. Chem. Soc. 2017, 139, 18142.
[45]
Zhang, P.; Wang, X. C.; Xuan, W.; Peng, P. X.; Li, Z. H.; Lu, R. Q.; Wu, S.; Tian, Z, Q.; Cao, X. Y. Chem. Commun. 2018, 54, 4685.
[46]
Chen, Y. X.; Wu, G. C.; Chen, B. B.; Qu, H.; Jiao, T. Y.; Li, Y. T.; Ge, C. Q.; Zhang, C.; Liang, L. X.; Zeng, X. Q.; Cao, X. Y.; Wang, Q.; Li, H. Angew. Chem., Int. Ed. 2021, 60, 18815.
[47]
Beaudoin, D.; Rominger, F.; Mastaler?, M. Angew. Chem., Int. Ed. 2017, 56, 1244.
[48]
Wagner, P.; Rominger, F.; Zhang, W. S.; Gross, J. H.; Elbert, S. M.; Schr?der, R. R.; Mastaler?, M. Angew. Chem., Int. Ed. 2021, 60, 8896.
[49]
Wang, X. C.; Peng, P. X.; Xuan, W.; Wang, Y.; Zhuang, Y. B.; Tian, Z. Q.; Cao, X. Y. Org. Biomol. Chem. 2018, 16, 34.
[50]
Jiao, T. Y.; Qu, H.; Tong, L.; Cao, X. Y.; Li, H. Angew. Chem., Int. Ed. 2021, 60, 9852.
[51]
Chen, L. J.; Reiss, P. S.; Chong, S. Y.; Holden, D.; Jelfs, K. E.; Hasell, T.; Little, M. A.; Kewley, A.; Briggs, M. E.; Stephenson, A.; Thomas, K. M.; Armstrong, J. A.; Bell, J.; Busto, J.; Noel, R.; Liu, J.; Strachan, D. M.; Thallapally, P. K.; Cooper, A. I. Nat. Mater. 2014, 13, 954.
[52]
Duan, A. H.; Wang, B. J.; Xie, S. M.; Zhang, J. H.; Yuan, L. M. Chirality 2017, 29, 172.
[53]
Wang, B. J.; Duan, A. H.; Zhang, J. H.; Xie, S. M.; Cao, Q. E.; Yuan, L. M. Molecules 2019, 24, 420.
[54]
Lu, Z. Y; Lu, X. T.; Zhong, Y. H.; Hu, Y. F.; Li, G. K.; Zhang, R. K. Anal. Chim. Acta 2019, 1050, 146.
[55]
Zhang, J. H.; Xie, S. M.; Chen, L.; Wang, B. J.; He, P. G.; Yuan, L. M. Anal. Chem. 2015, 87, 7817.
[56]
Kewley, A.; Stephenson, A.; Chen, L. J.; Briggs, M. E.; Hasell, T.; Cooper, A. I. Chem. Mater. 2015, 27, 3207.
[57]
Xie, S. M.; Zhang, J. H.; Fu, N.; Wang, B. J.; Chen, L.; Yuan, L. M. Anal. Chim. Acta 2016, 903, 156.
[58]
Zhang, J. H.; Xie, S. M.; Wang, B. J.; He, P. G.; Yuan, L. M. J. Chromatogr. A 2015, 1426, 174.
[59]
Xie, S. M.; Zhang, J. H.; Fu, N.; Wang, B. J.; Hu, C.; Yuan, L. M. Molecules 2016, 21, 1466.
[60]
Zhang, J. H.; Xie, S. M.; Wang, B. J.; He, P. G.; Yuan, L. M. J. Sep. Sci. 2018, 41, 1385.
[61]
Wang, Z. M.; Cui, Y. Y.; Yang, C. X.; Yan, X. P. ACS Appl. Nano Mater. 2020, 3, 479.
[62]
Zhang, J. H.; Zhu, P. J.; Xie, S. M.; Zi, M.; Yuan, L. M. Anal. Chim. Acta 2018, 999, 169.
[63]
Wang, Y.; Chen, J. K.; Xiong, L. X.; Wang, B. J.; Xie, S. M.; Zhang, J. H.; Yuan, L. M. Anal. Chem. 2022, 94, 4961.
[64]
Li, K.; Xiong, L. X.; Wang, Y.; Zhang, Y. P.; Wang, B. J.; Xie, S. M.; Zhang, J. H.; Yuan, L. M. J. Chromatogr. A 2022, 1679, 463415.
[65]
Liang, R. X.; Zhang, Y. P.; Zhang, J. H.; Gong, Y. N.; Huang, B.; Wang, B. J.; Xie, S. M.; Yuan, L. M. J. Chromatogr. A 2023, 1711, 464444.
[66]
Sun, S. S.; Wang, L. T.; Wang, J. S.; Lv, W. J.; Yu, Q. H.; Pei, D.; Han, S. Q.; Li, X. Y.; Wang, M.; Liu, S.; Quan, X. G.; Lv, M. J. Sep. Sci. 2023, 46, 2200935.
[67]
Sun, J. K; Zhan, W. W.; Akita, T.; Xu, Q. J. Am. Chem. Soc. 2015, 137, 7063.
[68]
Zhang, Y.; Xiong, Y.; Ge, J.; Lin, R.; Chen, C.; Peng, Q.; Wang, D. S.; Li, Y. D. Chem. Commun. 2018, 54, 2796.
[69]
Yang, X. C.; Sun, J. K.; Kitta, M.; Pang, H.; Xu, Q. Nat. Catal. 2018, 1, 214.
[70]
Wang, K. X.; Tang, X. H.; Anjali, B. A.; Dong, J. Q.; Jiang, J. W.; Liu, Y.; Cui, Y. J. Am. Chem. Soc. 2024, 146, 6638.
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