Citation: Yu Pang, Min Wang, Ning-Hua Yang, Min Xue, Yong Yang. One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure[J]. Chinese Chemical Letters, ;2024, 35(10): 109575. doi: 10.1016/j.cclet.2024.109575 shu

One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure

Yu Pang ^a ,
Min Wang ^a ,
Ning-Hua Yang ^b ,
Min Xue ^{a, *,} ,
Yong Yang ^{b, *,}

a.
School of Science, Department of Physics, Key Laboratory of Optical Field Manipulation of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China
b.
School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China

minxue@zstu.edu.cn

yangyong@zstu.edu.cn

Received Date: 30 September 2023
Revised Date: 15 January 2024
Accepted Date: 28 January 2024
Available Online: 29 January 2024

Figures(3)

Trifluoroacetic acid (TFA) catalyzed condensation reaction between tetraaminooxacalix[4]arene and N-alkylcarbazole-3,6-dicarbaldehyde in CH₂Cl₂ afforded a single product in 87%–89% yield. Well-defined yet undissolvable ¹H NMR spectra suggested formation of robust and discrete structures in solution. X-ray single crystal analysis further revealed a giant twisted double-layer chiral macrocycle in the solid state, which was formed from [4 + 8] condensation of the two reactants via 16 imine bonds. DFT calculations discovered that only the [4 + 8] twisted product is thermodynamically favorable, which accounts for its highly selective and efficient formation out of a library of many other combinations.
- One-pot synthesis,
- Oxacalix[4]arene,
- Dynamic covalent chemistry,
- Chiral macrocycle,
- X-ray single crystal
1. [1]
  J.M. Lehn, A.V. Eliseev, Science 291 (2001) 2331–2332. doi: 10.1126/science.1060066
2. [2]
  S.J. Rowan, S.J. Cantrill, G.R.L. Cousins, J.K.M. Sanders, J.F. Stoddart, Angew. Chem. Int. Ed. 41 (2002) 898–952. doi: 10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E
3. [3]
  P.T. Corbett, J. Leclaire, L. Vial, et al., Chem. Rev. 106 (2006) 3652–3711. doi: 10.1021/cr020452p
4. [4]
  Y. Jin, C. Yu, R.J. Denman, W. Zhang, Chem. Soc. Rev. 42 (2013) 6634–6654. doi: 10.1039/c3cs60044k
5. [5]
  T. Santos, D.S. Rivero, Y. Pérez-Pérez, et al., Angew. Chem. Int. Ed. 60 (2021) 18783–18791. doi: 10.1002/anie.202106230
6. [6]
  W.J. Ong, T.M. Swager, Nat. Chem. 10 (2018) 1023–1030. doi: 10.1038/s41557-018-0122-8
7. [7]
  H. Takahagi, S. Fujibe, N. Iwasawa, Chem. Eur. J. 15 (2009) 13327–13330. doi: 10.1002/chem.200902564
8. [8]
  K. Kataoka, T.D. James, Y. Kubo, J. Am. Chem. Soc. 129 (2007) 15126–15127. doi: 10.1021/ja076792f
9. [9]
  S. Klotzbach, F. Beuerle, Angew. Chem. Int. Ed. 54 (2015) 10356–10360. doi: 10.1002/anie.201502983
10. [10]
  M. Mastalerz, Acc. Chem. Res. 51 (2018) 2411–2422. doi: 10.1021/acs.accounts.8b00298
11. [11]
  I. Maric, L. Yang, X. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202216475. doi: 10.1002/anie.202216475
12. [12]
  Y. Lei, Q. Chen, P. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 4705–4711. doi: 10.1002/anie.202013045
13. [13]
  T. Jiao, G. Wu, Y. Zhang, et al., Angew. Chem. Int. Ed. 59 (2020) 18350–18367. doi: 10.1002/anie.201910739
14. [14]
  J.R. Nitschke, Angew. Chem. Int. Ed. 43 (2004) 3073–3075. doi: 10.1002/anie.200454082
15. [15]
  X. Liu, Y. Liu, G. Li, R. Warmuth, Angew. Chem. Int. Ed. 45 (2006) 901–904. doi: 10.1002/anie.200504049
16. [16]
  W.B. Gao, Z. Li, T. Tong, et al., J. Am. Chem. Soc. 145 (2023) 17795–17804. doi: 10.1021/jacs.3c04761
17. [17]
  W. Ma, Q. Zheng, Y. He, et al., J. Am. Chem. Soc. 141 (2019) 18271–18277. doi: 10.1021/jacs.9b09189
18. [18]
  X. Liu, X. Yang, X. Ding, et al., Chin. Chem. Lett. 34 (2023) 108148. doi: 10.1016/j.cclet.2023.108148
19. [19]
  Q. Li, J.D. Sun, B. Yang, et al., Chin. Chem. Lett. 33 (2022) 1988–1992. doi: 10.1016/j.cclet.2021.10.017
20. [20]
  P.D. Frischmann, J. Jiang, J.K.H. Hui, J.J. Grzybowski, M.J. MacLachlan, Org. Lett. 10 (2008) 1255–1258. doi: 10.1021/ol8001317
21. [21]
  A. Li, S. Xiong, W. Zhou, et al., Chem. Commun. 57 (2021) 4496–4499. doi: 10.1039/D1CC01158H
22. [22]
  W. Maes, W. Dehaen, Chem. Soc. Rev. 37 (2008) 2393–2402. doi: 10.1039/b718356a
23. [23]
  M.X. Wang, Acc. Chem. Res. 45 (2012) 182–195. doi: 10.1021/ar200108c
24. [24]
  P. Neri, J.L. Sessler, M.X. Wang, Calixarenes and Beyond, Springer International Publishing, 2016, pp. 399–420.
25. [25]
  V. Mehta, M. Panchal, K. Modi, et al., Curr. Org. Chem. 19 (2015) 1077–1096. doi: 10.2174/1385272819666150318221724
26. [26]
  W.H. Mi, T.Y. Huang, Y.F. Ao, et al., Chin. Chem. Lett. 35 (2024) 109077. doi: 10.1016/j.cclet.2023.109077
27. [27]
  M.X. Wang, H.B. Yang, J. Am. Chem. Soc. 126 (2004) 15412–15422. doi: 10.1021/ja0465092
28. [28]
  J.L. Katz, M.B. Feldman, R.R. Conry, Org. Lett. 7 (2005) 91–94. doi: 10.1021/ol047840t
29. [29]
  Y. Yang, M. Xue, C.F. Chen, CrystEngComm 12 (2010) 3502–3505. doi: 10.1039/b927446d
30. [30]
  J.X. Ma, X. Fang, M. Xue, Y. Yang, Org. Biomol. Chem. 17 (2019) 5075–5085. doi: 10.1039/C9OB00613C
31. [31]
  S.G. Wang, Y. Pang, M. Xue, Y. Yang, New J. Chem. 45 (2021) 19219–19223. doi: 10.1039/D1NJ04034K
32. [32]
  Y.X. Li, M. Xue, Y. Yang, Org. Lett. 23 (2021) 6435–6438. doi: 10.1021/acs.orglett.1c02255
33. [33]
  M. Mastalerz, Angew. Chem. Int. Ed. 49 (2010) 5042–5053. doi: 10.1002/anie.201000443
34. [34]
  K. Acharyya, P.S. Mukherjee, Angew. Chem. Int. Ed. 58 (2019) 8640–8653. doi: 10.1002/anie.201900163
35. [35]
  Y. Cohen, L. Avram, L. Frish, Angew. Chem. Int. Ed. 44 (2005) 520–554. doi: 10.1002/anie.200300637
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