Chinese Journal of Organic Chemistry >
Synthesis and Application of Chiral Organic Imine Molecular Cages
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)
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.
Key words: porous organic molecular cage; chirality; imine; synthetic strategy; self-assembly
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
| [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. |
/
| 〈 |
|
〉 |