Citation: Yi Zhou, Wei Zhang, Rong Fu, Jiaxin Dong, Yuxuan Liu, Zihang Song, Han Han, Kang Cai. Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands[J]. Chinese Chemical Letters, ;2025, 36(2): 109865. doi: 10.1016/j.cclet.2024.109865 shu

Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands

Yi Zhou ^a ,
Wei Zhang ^a ,
Rong Fu ^a ,
Jiaxin Dong ^a ,
Yuxuan Liu ^a ,
Zihang Song ^a ,
Han Han ^{b, c, *,} ,
Kang Cai ^{a, *,}

a.
College of Chemistry, Nankai University, Tianjin 300071, China
b.
Department of Chemistry, Northwestern University, Evanston, IL 60208, United States
c.
Department of Chemistry, The University of Hong Kong, Hong Kong SAR 999077, China

hanhan23@hku.hk

kangcai@nankai.edu.cn

Received Date: 20 January 2024
Revised Date: 26 March 2024
Accepted Date: 7 April 2024
Available Online: 9 April 2024

Figures(7)

Chiral coordination molecular cages/capsules with discrete nanoconfined chiral cavities demonstrate significant potential applications across various fields. In this study, we utilized Tröger's base as the building block to design and synthesize two pairs of enantiopure ligands. These ligands were then self-assembled with Pd(Ⅱ) ions through chiral self-sorting coordination, resulting in the formation of two pairs of homochiral M₂L₄-type coordination molecular capsules. Notably, due to differences in the substitution positions on the Tröger's base, these two pairs of enantiomeric coordination molecular capsules exhibited distinct levels of cavity closures, cavity sizes, and host-guest recognition properties. This research offers valuable insights into the construction of novel chiral molecular capsules and the regulation of confined cavities.
- Metal-organic capsule,
- Chirality,
- Self-sorting,
- Tröger's base,
- Host-guest recognition
1. [1]
  C.L. Liu, E.O. Bobylev, S. Dauriac, et al., CCS Chem. 5 (2023) 1–31. doi: 10.31635/ccschem.022.202201214ed1
2. [2]
  Y. Li, J. Dong, W. Gong, et al., J. Am. Chem. Soc. 143 (2021) 20939–20951. doi: 10.1021/jacs.1c09992
3. [3]
  Y.P. Wang, Y. Zhang, X.H. Duan, et al., Coord. Chem. Rev. 501 (2024) 215570. doi: 10.1016/j.ccr.2023.215570
4. [4]
  S. Pullen, J. Tessarolo, G.H. Clever, Chem. Sci. 12 (2021) 7269–7293. doi: 10.1039/d1sc01226f
5. [5]
  A. Walther, I. Regeni, J.J. Holstein, G.H. Clever, J. Am. Chem. Soc. 145 (2023) 25365–25371. doi: 10.1021/jacs.3c09295
6. [6]
  J. Gemen, J.R. Church, T.P. Ruoko, et al., Science 381 (2023) 1357–1363. doi: 10.1126/science.adh9059
7. [7]
  D. Zhang, T.K. Ronson, Y.Q. Zou, J.R. Nitschke, Nat. Rev. Chem. 5 (2021) 168–182. doi: 10.1038/s41570-020-00246-1
8. [8]
  R. Banerjee, D. Chakraborty, P.S. Mukherjee, J. Am. Chem. Soc., 145 (2023) 7692–7711. doi: 10.1021/jacs.3c01084
9. [9]
  S.P. Zheng, Y.W. Xu, P.Y. Su, et al., Chin. Chem. Lett. 35 (2024) 108477. doi: 10.1016/j.cclet.2023.108477
10. [10]
  Z.X. Lian, X.Z. Wang, C.W. Zhou, et al., Chin. Chem. Lett. 35 (2024) 109063. doi: 10.1016/j.cclet.2023.109063
11. [11]
  G. Wu, Y. Chen, S. Fang, et al., Angew. Chem. Int. Ed. 60 (2021) 16594–16599. doi: 10.1002/anie.202104164
12. [12]
  Y.H. Huang, Y.L. Lu, X.D. Zhang, et al., Angew. Chem. Int. Ed. 63 (2024) e202315053. doi: 10.1002/anie.202315053
13. [13]
  G. Li, T.K. Ronson, R. Lavendomme, et al., Chem. 9 (2023) 1549–1561. doi: 10.1016/j.chempr.2023.03.011
14. [14]
  S.J. Hu, X.Q. Guo, L.P. Zhou, et al., J. Am. Chem. Soc. 144 (2022) 4244–4253. doi: 10.1021/jacs.2c00760
15. [15]
  W. Xue, L. Pesce, A. Bellamkonda, et al., J. Am. Chem. Soc. 145 (2023) 5570–5577. doi: 10.1021/jacs.3c00294
16. [16]
  Y.J. Hou, K. Wu, Z.W. Wei, et al., J. Am. Chem. Soc. 140 (2018) 18183–18191. doi: 10.1021/jacs.8b11152
17. [17]
  J.S. Wang, K. Wu, C. Yin, et al., Nat. Commun. 11 (2020) 4675. doi: 10.1038/s41467-020-18487-5
18. [18]
  K. Li, K. Wu, Y.L. Lu, et al., Angew. Chem. Int. Ed. 61 (2022) e202114070. doi: 10.1002/anie.202114070
19. [19]
  G.R. Genov, H. Takezawa, H. Hayakawa, M. Fujita, J. Am. Chem. Soc. 145 (2023) 17013–17017. doi: 10.1021/jacs.3c06301
20. [20]
  W. Gong, W. Wang, J. Dong, et al., CCS Chem. 5 (2023) 2736–2759. doi: 10.31635/ccschem.023.202303348
21. [21]
  J. Dong, Y. Liu, Y. Cui, Acc. Chem. Res. 54 (2021) 194–206. doi: 10.1021/acs.accounts.0c00604
22. [22]
  L. Zhang, H. Liu, G. Yuan, Y.F. Han, Chin. J. Chem. 39 (2021) 2273–2286. doi: 10.1002/cjoc.202100180
23. [23]
  D. Didier, B. Tylleman, N. Lambert, et al., Tetrahedron. 64 (2008) 6252–6262. doi: 10.1016/j.tet.2008.04.111
24. [24]
  D.L. Jameson, T. Field, M.R. Schmidt, et al., J. Org. Chem. 78 (2013) 11590–11596. doi: 10.1021/jo401873x
25. [25]
  E.O. Bobylev, J. Ruijter, D.A. Poole Ⅲ, et al., Angew. Chem. Int. Ed. 62 (2023) e202218162. doi: 10.1002/anie.202218162
26. [26]
  M. Fujita, D. Oguro, M. Miyazawa, et al., Nature 378 (1995) 469–471. doi: 10.1038/378469a0
27. [27]
  K. Iizuka, H. Takezawa, M. Fujita, J. Am. Chem. Soc. 145 (2023) 25971–25975. doi: 10.1021/jacs.3c10720
28. [28]
  N. Kishi, Z. Li, K. Yoza, M. Akita, M. Yoshizawa, J. Am. Chem. Soc. 133 (2011) 11438–11441. doi: 10.1021/ja2037029
29. [29]
  M. Shuto, R. Sumida, M. Yuasa, T. Sawada, M. Yoshizawa, JACS. Au 3 (2023) 2905–2911. doi: 10.1021/jacsau.3c00484
30. [30]
  J.L. Bolliger, A.M. Belenguer, J.R. Nitschke, Angew. Chem. Int. Ed. 52 (2013) 7958–7962. doi: 10.1002/anie.201302136
31. [31]
  Y. Yang, T.K. Ronson, J. Zheng, N. Mihara, J.R. Nitschke, Chem 9 (2023) 1–11. doi: 10.1016/j.chempr.2022.12.012
32. [32]
  P. Howlader, S. Mondal, S. Ahmed, P.S. Mukherjee, J. Am. Chem. Soc. 142 (2020) 9070–9078. doi: 10.1021/jacs.0c03551
33. [33]
  D. Samanta, S. Mukherjee, Y.P. Patil, P.S. Mukherjee, Chem. Eur. J. 18 (2012) 12322–12329. doi: 10.1002/chem.201201679
34. [34]
  C.S. Arribas, O.F. Wendt, A.P. Sundin, et al., Chem. Commun. 46 (2010) 4381–4383. doi: 10.1039/b927030b
35. [35]
  M. Han, D.M. Engelhard, G.H. Clever, Chem. Soc. Rev. 43 (2014) 1848–1860. doi: 10.1039/C3CS60473J
36. [36]
  G.H. Clever, P. Punt, Acc. Chem. Res. 50 (2017) 2233–2243. doi: 10.1021/acs.accounts.7b00231
37. [37]
  J.B. Maglic, R. Lavendomme, J. Appl. Crystallogr. 55 (2022) 1033–1044. doi: 10.1107/s1600576722004988
38. [38]
  S. Pullen, G.H. Clever, Acc. Chem. Res. 51 (2018) 3052–3064. doi: 10.1021/acs.accounts.8b00415
39. [39]
  K. Wu, J. Tessarolo, A. Baksi, G.H. Clever, Angew. Chem. Int. Ed. 61 (2022) e202205725. doi: 10.1002/anie.202205725
40. [40]
  C. Bannwarth, E. Caldeweyher, S. Ehlert, et al., WIREs Comput. Mol. Sci. 11 (2021) e1493. doi: 10.1002/wcms.1493
41. [41]
  R. Fu, Q.Y. Zhao, H. Han, et al., Angew. Chem. Int. Ed. 62 (2023) e202315990. doi: 10.1002/anie.202315990
42. [42]
  Y.L. Lai, J. Su, L.X. Wu, et al., Chin. Chem. Lett. 35 (2024) 108326. doi: 10.1016/j.cclet.2023.108326
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2. [2]
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沈阳化工大学材料科学与工程学院沈阳 110142

Self-assembly of two pairs of homochiral M2L4 coordination capsules with varied confined space using Tröger's base ligands

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通讯作者: 陈斌, bchen63@163.com

Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands