Citation: Chengyuan Yu, Xiaodong Wang, Cai-Xin Zhao, Shun Yang, Jiaan Gan, Zhuo Wang, Zhanqi Cao, Da-Hui Qu. Optically probing molecular shuttling motion of [2]rotaxane by a conformation-adaptive fluorophore[J]. Chinese Chemical Letters, ;2022, 33(11): 4904-4907. doi: 10.1016/j.cclet.2022.03.004 shu

Optically probing molecular shuttling motion of [2]rotaxane by a conformation-adaptive fluorophore

Chengyuan Yu ^a ,
Xiaodong Wang ^a ,
Cai-Xin Zhao ^a ,
Shun Yang ^a ,
Jiaan Gan ^b ,
Zhuo Wang ^b ,
Zhanqi Cao ^{c, *,} ,
Da-Hui Qu ^{a, *,}

a.
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
Shanghai Gantian Optical Material Co., Ltd., Shanghai 201512, China
c.
College of Science, Henan Agricultural University, Zhengzhou 450002, China

zqcao@henau.edu.cn

dahui_qu@ecust.edu.cn

Received Date: 29 December 2021
Revised Date: 24 February 2022
Accepted Date: 2 March 2022
Available Online: 5 March 2022

Figures(4)

A bistable [2]rotaxane with a conformation-adaptive macrocycle bearing a 9, 14-diphenyl-9, 14-dihydrodibenzo[a, c]phenazine (DPAC) unit was synthesized, which could be utilized to optical probe the molecular shuttling motion of the functionalized rotaxane system. The UV–vis, ¹H NMR and PL spectroscopic data clearly demonstrated that the DPAC ring was interlocked onto the thread and the fluorescence intensity of the DPAC unit in the macrocycle was effectively regulated by the location change of the macrocycle along the thread under acid/base stimulation, which was attributed to the modulation of the intramolecular photo-induced electron transfer between the DPAC unit and the methyltriazole (MTA) unit. This bistable rotaxane system containing a conformation-adaptive fluorophore unit in the macrocycle moiety opens an alternative way to design functional bistable mechanically interlocked molecules.
- [2]Rotaxane,
- Optically probe,
- Mechanical shuttling,
- Molecular conformations,
- Conformation-adaptive macrocycle
1. [1]
  J.M. Lehn, Science 227 (1985) 849–856. doi: 10.1126/science.227.4689.849
2. [2]
  J.M. Lehn, Science 260 (1993) 1762–1763. doi: 10.1126/science.8511582
3. [3]
  Y. Zhou, B.T. Zhao, Y. Liu, Photoluminescent Crown Ether Assembly, in: Y. Liu (Ed.), Handbook of Macrocyclic Supramolecular Assembly, Springer Nature, 2020, pp. 103–133.
4. [4]
  D.G. Barnes, M. Vidiassov, B. Ruthensteiner, et al., PLoS One 8 (2013) e69446. doi: 10.1371/journal.pone.0069446
5. [5]
  J.F. Stoddart, Angew. Chem. Int. Ed. 56 (2017) 11094–11125. doi: 10.1002/anie.201703216
6. [6]
  C. Clavel, C. Romuald, E. Brabet, F. Coutrot, Chem. Eur. J. 19 (2013) 2982–2989. doi: 10.1002/chem.201203597
7. [7]
  C.X. Zhao, Q. Zhang, G. London, D.H. Qu, Functional rotaxanes, in: D.H. Qu (Ed.), Handbook of Macrocyclic Supramolecular Assembly, Springer Nature, 2020, pp. 277–310.
8. [8]
  Q. He, G.I. Vargas-Zuniga, S.H. Kim, S.K. Kim, J.L. Sessler, Chem. Rev. 119 (2019) 9753–9835. doi: 10.1021/acs.chemrev.8b00734
9. [9]
  T.L. Mako, J.M. Racicot, M. Levine, Chem. Rev. 119 (2019) 322–477. doi: 10.1021/acs.chemrev.8b00260
10. [10]
  Z. Ke, K. Chen, Z. Li, et al., Chin. Chem. Lett. 32 (2021) 3109–3112. doi: 10.1016/j.cclet.2021.03.043
11. [11]
  C. Chen, Y. Chen, X. Dai, et al., Chem. Commun. 57 (2021) 2812–2815. doi: 10.1039/D1CC00292A
12. [12]
  T. Xiao, J. Wang, Y. Shen, et al., Chin. Chem. Lett. 32 (2021) 1377–1380. doi: 10.1016/j.cclet.2020.10.037
13. [13]
  T. Xiao, L. Zhou, X.Q. Sun, et al., Chin. Chem. Lett. 31 (2020) 1–9. doi: 10.1016/j.cclet.2019.05.011
14. [14]
  H. Wu, T. Xiao, Frontiers Chem. 8 (2020) 610093. doi: 10.3389/fchem.2020.610093
15. [15]
  T. Xiao, W. Zhong, W. Yang, et al., Chem. Commoun. 56 (2020) 14385–14388. doi: 10.1039/D0CC06381A
16. [16]
  Z. Cao, D. Wu, M. Li, et al., Chin. Chem. Lett. 33 (2022) 1533–1536. doi: 10.1016/j.cclet.2021.09.001
17. [17]
  M. Gauthier, F. Coutrot, Chemistry (Easton) 27 (2021) 17576–17580.
18. [18]
  L. Liu, Q. Wang, M. Cheng, et al., Asian J. Org. Chem. 4 (2015) 221–225. doi: 10.1002/ajoc.201402155
19. [19]
  J.Y.C. Lim, P.D. Beer, Eur. J. Org. Chem. 2019 (2019) 3433–3441. doi: 10.1002/ejoc.201801571
20. [20]
  E.M. Perez, D.T. Dryden, D.A. Leigh, G. Teobaldi, F. Zerbetto, J. Am. Chem. Soc. 126 (2004) 12210–12211. doi: 10.1021/ja0484193
21. [21]
  T.T.K. Cuc, P.Q. Nhien, T.M. Khang, et al., Chem. Mater. 32 (2020) 9371–9389. doi: 10.1021/acs.chemmater.0c03314
22. [22]
  H. Li, J.N. Zhang, W. Zhou, et al., Org. Lett. 15 (2013) 3070–3073. doi: 10.1021/ol401251u
23. [23]
  Y. Liu, Q. Zhang, W.H. Jin, et al., Chem. Commun. 54 (2018) 10642–10645. doi: 10.1039/C8CC05886E
24. [24]
  Z. Zhang, Y.S. Wu, K.C. Tang, et al., J. Am. Chem. Soc. 137 (2015) 8509–8520. doi: 10.1021/jacs.5b03491
25. [25]
  H.V. Humeniuk, A. Rosspeintner, G. Licari, et al., Angew. Chem. Int. Ed. 57 (2018) 10559–10563. doi: 10.1002/anie.201804662
26. [26]
  A.L. Antaris, H. Chen, K. Cheng, et al., Nat. Mater. 15 (2016) 235–242. doi: 10.1038/nmat4476
27. [27]
  W. Chen, C.L. Chen, Z. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 1636–1644. doi: 10.1021/jacs.6b11789
28. [28]
  Z. Zhang, C.L. Chen, Y.A. Chen, et al., Angew. Chem. Int. Ed. 57 (2018) 9880–9884. doi: 10.1002/anie.201806385
29. [29]
  S. Yang, C. -. X. Zhao, S. Crespi, et al., Chem 6 (2021) 1544–1556.
30. [30]
  W. Chen, C. Guo, Q. He, et al., J. Am. Chem. Soc. 141 (2019) 14798–14806. doi: 10.1021/jacs.9b07170
31. [31]
  T. Miura, Y. Urano, K. Tanaka, et al., J. Am. Chem. Soc. 125 (2003) 8666– 8671. doi: 10.1021/ja035282s
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