Citation: Hui-Juan Wang, Heng-Yi Zhang, Wen-Wen Xing, Huang Wu, Yong-Liang Cui, Yu Liu. Photodimerization-induced transition of helixes to vesicles based on coumarin-12-crown-4[J]. Chinese Chemical Letters, ;2022, 33(8): 4033-4036. doi: 10.1016/j.cclet.2021.12.051 shu

Photodimerization-induced transition of helixes to vesicles based on coumarin-12-crown-4

Hui-Juan Wang ^a ,
Heng-Yi Zhang ^a ,
Wen-Wen Xing ^a ,
Huang Wu ^b ,
Yong-Liang Cui ^a ,
Yu Liu ^{a, *,}

a.
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
b.
Department of Chemistry, Northwestern University, Evanston, IL 60208, United States

yuliu@nankai.edu.cn

Received Date: 27 September 2021
Revised Date: 15 December 2021
Accepted Date: 22 December 2021
Available Online: 26 December 2021

Figures(5)

Rational construction of fine-tuning and precisely controllable topological nanostructures based on supramolecular self-assembly system remains a challenge. Herein, coumarin-12-crown-4 (1) as a building block was synthesized by one-pot method and showed reversible high stereo-selective photodimerization (anti-head-to-head dimer (anti-HH-1): syn-head-to-head dimer (syn-HH-1) = 10.8:1) and photocleavage. Helical nanobelts were formed by the self-assembly of 1 through asymmetrical H-bonds, which were in concordance with the crystal state superstructure. Upon irradiation with 365 nm light, these nanobelts transformed into nanoballs which were constructed by three building blocks. Further, we investigated the photoreaction of 1 and got two pure covalent dimers (anti-HH-1 and syn-HH-1). The anti-HH-1 self-assembled into hollow micro-vesicles. The transformation of superstructures based on photo-controlled multiple blocks shines a light to the research on the relationship between molecules and superstructures.
- Reversible photodimerization,
- Superstructures,
- Coumarin,
- Supramolecular self-assembly,
- Molecular stacking
1. [1]
  X. Dou, N. Mehwish, C. Zhao, et al., Acc. Chem. Rev.53 (2020) 852–862. doi: 10.1021/acs.accounts.0c00012
2. [2]
  X. Zhou, H. Zhao, S. Liu, et al., Chin. Chem. Lett. 32 (2021) 761–764. doi: 10.1016/j.cclet.2020.05.023
3. [3]
  P. Xing, Y. Zhao, Adv. Mater. 28 (2016) 7304–7339. doi: 10.1002/adma.201600906
4. [4]
  J.H. Jung, Y. Ono, K. Sakurai, M. Sano, S. Shinkai, J. Am. Chem. Soc. 122 (2000) 8648–8653;. doi: 10.1021/ja001623f
5. [5]
  L. Li, W. Tuo, Q. Zhu, et al., J. Am. Chem. Soc. 142 (2020) 20583–20587. doi: 10.1021/jacs.0c10901
6. [6]
  S. Yagai, Y. Kitamoto, S. Datta, B. Adhikari, Acc. Chem. Res. 52 (2019) 1325–1335. doi: 10.1021/acs.accounts.8b00660
7. [7]
  L. Zhang, Y.M. Zhang, G.X. Liu, Y. Liu, Chin. Chem. Lett. 30 (2019) 120–122. doi: 10.1016/j.cclet.2018.04.028
8. [8]
  P. Xing, Y. Li, Y. Wang, et al., Angew. Chem. Int. Ed. 57 (2018) 7774–7779. doi: 10.1002/anie.201802825
9. [9]
  G. Yu, M. Xue, Z. Zhang, et al., J. Am. Chem. Soc. 134 (2012) 13248–13251. doi: 10.1021/ja306399f
10. [10]
  T. Zhang, Y.H. Liu, B.W. Hu, et al., Chin. Chem. Lett. 30 (2019) 949–952. doi: 10.1016/j.cclet.2018.12.029
11. [11]
  G. Liu, J. Sheng, W.L. Teo, et al., J. Am. Chem. Soc. 140 (2018) 16275–16283. doi: 10.1021/jacs.8b10024
12. [12]
  H.L. Sun, Y. Chen, X. Han, Y. Liu, Angew. Chem. Int. Ed. 56 (2017) 7062–7065. doi: 10.1002/anie.201612629
13. [13]
  S. Yagai, M. Yamauchi, A. Kobayashi, et al., J. Am. Chem. Soc. 134 (2012) 18205–18208. doi: 10.1021/ja308519b
14. [14]
  M. Yamauchi, T. Ohba, T. Karatsu, S. Yagai, Nat. Commun. 6 (2015) 8936. doi: 10.1038/ncomms9936
15. [15]
  J. Zhang, Q. Zou, H. Tian, Adv. Mater. 25 (2013) 378–399. doi: 10.1002/adma.201201521
16. [16]
  H. He, M. Feng, Q. Chen, X. Zhang, H. Zhan, Angew. Chem. Int. Ed. 55 (2016) 936–940. doi: 10.1002/anie.201508355
17. [17]
  Y. Cao, Y. Chen, Z. Zhang, et al., Chin. Chem. Lett. 32 (2021) 349–352. doi: 10.1016/j.cclet.2020.03.058
18. [18]
  S.R. Trenor, A.R. Shultz, B.J. Love, E.T. Long, Chem. Soc. Rev. 104 (2004) 3059–3077. doi: 10.1021/cr030037c
19. [19]
  J.W. Chung, K. Lee, C. Neikirk, C.M. Nelson, Small 8 (2012) 1693–1700. doi: 10.1002/smll.201102263
20. [20]
  P.P. Jia, L. Xu, Y.X. Hu, et al., J. Am. Chem. Soc. 143 (2021) 399–408. doi: 10.1021/jacs.0c11370
21. [21]
  H. Yan, F. Huo, Y. Yue, J. Chao, C. Yin, J. Am. Chem. Soc. 143 (2021) 318–325. doi: 10.1021/jacs.0c10840
22. [22]
  J. Motoyanagi, T. Fukushima, N. Ishii, T. Aida, J. Am. Chem. Soc. 128 (2006) 4220–4221. doi: 10.1021/ja060593z
23. [23]
  F. Wang, H. Qiu, C. Feng, Adv. Funct. Mater. 30 (2020) 2002936. doi: 10.1002/adfm.202002936
24. [24]
  S. Wang, M.C. Forster, K. Xue, et al., Angew. Chem. Int. Ed. 60 (2021) 9712–9718. doi: 10.1002/anie.202100153
25. [25]
  J.H. Jung, H. Kobayashi, M. Masuda, T. Shimizu, S. Shinkai, J. Am. Chem. Soc. 123 (2001) 8785–8789. doi: 10.1021/ja010508h
26. [26]
  H. Fenniri, B.L. Deng, A.E. Ribbe, et al., Proc. Natl. Acad. Sci. U. S. A. 99 (2002) 6487–6492. doi: 10.1073/pnas.032527099
27. [27]
  H. Fenniri, B.L. Deng, A.E. Ribbe, J. Am. Chem. Soc. 124 (2002) 11064–11072. doi: 10.1021/ja026164s
28. [28]
  J.H. Jung, Y. Ono, K. Sakurai, M. Sano, S. Shinkai, J. Am. Chem. Soc. 122 (2000) 8648–8653. doi: 10.1021/ja001623f
29. [29]
  J.H. Jung, H. Kobayashi, M. Masuda, T. Shimizu, S. Shinkai, J. Am. Chem. Soc. 123 (2001) 8785–8789.
30. [30]
  J.H. Jung, Y. Ono, S. Shinkai, Langmuir 16 (2000) 1643–1649.
31. [31]
  H. Engelkamp, S. Middelbeek, R.J.M. Nolte, Science 284 (1999) 785–788.
32. [32]
  H.J. Wang, H.Y. Zhang, H. Wu, et al., Chem. Commun. 55 (2019) 4499–4502. doi: 10.1039/c9cc01874c
33. [33]
  W. Zhang, Y.M. Zhang, S.H. Li, et al., Angew. Chem. Int. Ed. 55 (2016) 11452–11456;. doi: 10.1002/anie.201605420
34. [34]
  P. Wei, H. Wang, K. Jie, F. Huang. Chem. Commun. 53 (2017) 1688–1691. doi: 10.1039/C6CC10089A
35. [35]
  G.M.J. Schmidt, Pure Appl. Chem. 27 (1971) 647–678. doi: 10.1351/pac197127040647
36. [36]
  S.R. Trenor, A.R. Shultz, B.J. Love, T.E. Long, Chem. Rev. 104 (2004) 3059–3078.
37. [37]
  X. Yu, D. Scheller, O. Rademacher, T. Wolff, J. Org. Chem. 68 (2003) 7386–7399. doi: 10.1021/jo034627m
38. [38]
  J. Jiang, B. Qi, M. Lepage, Y. Zhao, Macromolecules 40 (2007) 790–792. doi: 10.1021/ma062493j
39. [39]
  N.K. Mal, M. Fujiwara, Y. Tanaka, Nature 421 (2003) 350–353.
40. [40]
  W. Ali, W. Gong, M. Hassan, et al., Chin. Chem. Lett. 32 (2021) 371–374.
41. [41]
  P.Y. Li, Y. Chen, Y. Liu, Chin. Chem. Lett. 30 (2019) 1190–1197.
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