Citation: Zhanqi Cao, Dongpu Wu, Mengzhen Li, Fan Yang, Zhikai Li, Wankai An, Song Jiang, Xin Zheng, Caoyuan Niu, Dahui Qu. An acid-base responsive linear-cyclic polymer rotaxane molecular shuttle with fluorescence signal output[J]. Chinese Chemical Letters, ;2022, 33(3): 1533-1536. doi: 10.1016/j.cclet.2021.09.001 shu

An acid-base responsive linear-cyclic polymer rotaxane molecular shuttle with fluorescence signal output

Zhanqi Cao ^{a, *,} ,
Dongpu Wu ^a ,
Mengzhen Li ^a ,
Fan Yang ^a ,
Zhikai Li ^c ,
Wankai An ^a ,
Song Jiang ^a ,
Xin Zheng ^a ,
Caoyuan Niu ^a ,
Dahui Qu ^{b, *,}

a.
College of Science, Henan Agricultural University, Zhengzhou 450002, China
b.
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
c.
College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen 518060, China

zqcao@henau.edu.cn

dahui_qu@ecust.edu.cn

Received Date: 30 May 2021
Revised Date: 28 August 2021
Accepted Date: 1 September 2021
Available Online: 27 September 2021

Figures(6)

The preparation of intelligent-responsive materials with controllable topology structure has long been a significant objective for chemists in the field of materials science. In this paper, we designed and prepared a linear-cyclic reversible topological structure polymer based on the bistable [1]rotaxane molecular shuttle. A ferrocene-functionalized [1]rotaxane and naphthalimide fluorophore group are introduced into the both ends of the polymer, which exhibit distance-induced photo-electron transfer effect. The structural transformation between linear and cyclic state of polymer is demonstrated by simple acid-base stimuli, accompanying visual fluorescence changes. The transformation process was characterized by ¹H NMR spectra and fluorescence spectra. This work provides a novel strategy to construct functionalized polymers with topological structure.
- Supramolecular polymer,
- Rotaxane molecular shuttle,
- Stimuli responsive,
- Fluorescence signal,
- Topological structure
1. [1]
  F.M. Haque, S.M. Grayson, Nat. Chem. 12 (2020) 433-444. doi: 10.1038/s41557-020-0440-5
2. [2]
  T.W. Wang, M.R. Golder, Polym. Chem. 12 (2021) 958-969. doi: 10.1039/D0PY01655A
3. [3]
  B.J. Ree, Y. Satoh, T. Isono, T. Satoh, Nano. Lett. 20 (2020) 6520-6525. doi: 10.1021/acs.nanolett.0c02268
4. [4]
  X. Ma, Y. L Zhao, Chem. Rev. 115 (2015) 7794-7839. doi: 10.1021/cr500392w
5. [5]
  L. Fang, X. Min, R. Kang, et al., Sci. Total Environ. 639 (2018) 110-117. doi: 10.1016/j.scitotenv.2018.05.103
6. [6]
  J. Yu, K. Li, L. Li, et al., Polym. Chem. 10 (2019) 2872-2880. doi: 10.1039/C9PY00334G
7. [7]
  B. Verbraeken, R. Hoogenboom, Angew. Chem. Int. Ed. 56 (2017) 7034-7036. doi: 10.1002/anie.201703418
8. [8]
  T. Josse, J.D. Winter, P. Gerbaux, O. Coulembier, Angew. Chem. Int. Ed. 55 (2016) 13944-13958. doi: 10.1002/anie.201601677
9. [9]
  Y.A. Chang, R.M. Waymouth, Inc. J. Polym. Sci., Part A: Polym. Chem. 55 (2017) 2892-2902. doi: 10.1002/pola.28635
10. [10]
  K. Naruse, A. Takasu, M. Higuchi, Macromol. Chem. Phys. 221 (2020) 2000004. doi: 10.1002/macp.202000004
11. [11]
  L. Zhang, Y. Wu, S. Li, Y. Zhang, K. Zhang, Macromolecules 53 (2020) 8621-8630. doi: 10.1021/acs.macromol.0c01511
12. [12]
  A. Narumi, M. Yamada, Y. Unno, et al., ACS Macro Lett. 8 (2019) 634-638. doi: 10.1021/acsmacrolett.9b00308
13. [13]
  T.W. Wang, P.R. Huang, J.L. Chow, W. Kaminsky, M.R. Golder, J. Am. Chem. Soc. 143 (2021) 7314-7319. doi: 10.1021/jacs.1c03491
14. [14]
  D. Aoki, G. Aibara, S. Uchida, T. Takata, J. Am. Chem. Soc. 139 (2017) 6791-6794. doi: 10.1021/jacs.7b01151
15. [15]
  M. Hartlieb, S. Catrouillet, A. Kuroki, et al., Chem. Sci. 10 (2019) 5476-5483. doi: 10.1039/C9SC00756C
16. [16]
  C. Wang, M.A. Olson, L. Fang, et al., Proc. Natl. Acad. Sci. U. S. A. 107 (2010) 13991-13996. doi: 10.1073/pnas.1009302107
17. [17]
  J.S. Wu, J.F. Stoddart, Mater. Chem. Front. 4 (2020) 1553. doi: 10.1039/D0QM90014A
18. [18]
  M. Wang, X. Du, H. Tian, et al., Chin. Chem. Lett. 30 (2019) 345-348. doi: 10.1016/j.cclet.2018.10.014
19. [19]
  X. Zeng, H. Deng, X. Jia, et al., Chem. Commun. 54 (2018) 11634-11637. doi: 10.1039/C8CC07188H
20. [20]
  H.Y. Zhou, Y. Han, C.F. Chen, Mater. Chem. Front. 4 (2020) 12-28. doi: 10.1039/C9QM00546C
21. [21]
  Y. Wang, Y. Zhang, Z. Zhou, et al., Nat. Commun. 11 (2020) 2727. doi: 10.1038/s41467-020-16556-3
22. [22]
  H. Chong, C. Nie, L. Wang, et al., Chin. Chem. Lett. 32 (2021) 57-61. doi: 10.1016/j.cclet.2020.11.020
23. [23]
  J.N. Zhang, H. Li, W. Zhou, et al., Chem. Eur. J. 19 (2013) 17192-17200. doi: 10.1002/chem.201303026
24. [24]
  S. Chen, Y. Wang, T. Nie, et al., J. Am. Chem. Soc. 140 (2018) 17992-17998. doi: 10.1021/jacs.8b09580
25. [25]
  Y. Han, C.Y. Nie, S. Jiang, J. Sun, C.G. Yan, Chin. Chem. Lett. 31 (2020) 725-728. doi: 10.1016/j.cclet.2019.09.014
26. [26]
  X. Han, F. Hu, H.J. Ge, S.H. Liu, J. Yin, Prog. Chem. 27 (2015) 675-686. doi: 10.7536/PC150129
27. [27]
  Z.Q. Cao, Y.C. Wang, A.H. Zou, et al., Chem. Commun. 53 (2017) 8683-8686. doi: 10.1039/C7CC05008A
28. [28]
  T. Xiao, L. Zhou, X.Q. Sun, et al., Chin. Chem. Lett. 31 (2020) 1-9. doi: 10.1016/j.cclet.2019.05.011
29. [29]
  Y. Wu, M. Frasconi, W.G. Liu, et al., J. Am. Chem. Soc. 142 (2020) 11835-11846. doi: 10.1021/jacs.0c03701
30. [30]
  E. Moulin, L. Faour, C.C. Carmona-Vargas, N. Giuseppone, Adv. Mater. 32 (2020) 1906036. doi: 10.1002/adma.201906036
31. [31]
  W.J. Li, W. Wang, X.Q. Wang, et al., J. Am. Chem. Soc. 142 (2020) 8473-8482. doi: 10.1021/jacs.0c02475
32. [32]
  T. Xiao, L. Xu, J. Götz, et al., Mater. Chem. Front. 3 (2019) 2738-2745. doi: 10.1039/C9QM00595A
33. [33]
  H. Li, X. Li, Z.Q. Cao, et al., ACS Appl. Mater. Interfaces 6 (2014) 18921-18929. doi: 10.1021/am506283g
34. [34]
  D.H. Qu, Q.C. Wang, Q.W. Zhang, X. Ma, H. Tian, Chem. Rev. 115 (2015) 7543-7588. doi: 10.1021/cr5006342
35. [35]
  M. Xue, Y. Yang, X. Chi, X. Yan, F. Huang, Chem. Rev. 115 (2015) 7398-7501. doi: 10.1021/cr5005869
36. [36]
  Q. Zhang, S.J. Rao, T. Xie, et al., Chem 4 (2018) 2670-2684. doi: 10.1016/j.chempr.2018.08.030
37. [37]
  C. Wang, S. Wang, H. Yang, et al., Angew. Chem. Int. Ed. 60 (2021) 14836-14840. doi: 10.1002/anie.202102838
38. [38]
  M. Li, H. Yan, C. Teh, V. Korzh, Y. Zhao, Chem. Commun. 50 (2014) 9745-9748. doi: 10.1039/C4CC02966F
39. [39]
  T. Xiao, J. Wang, Y. Shen, et al., Chin. Chem. Lett. 32 (2021) 1377-1380. doi: 10.1016/j.cclet.2020.10.037
40. [40]
  Q. Zhou, P. Wei, Y. Zhang, Y. Yu, X. Yan, Org. Lett. 15 (2013) 5350-5353. doi: 10.1021/ol402607x
41. [41]
  X.S. Du, C.Y. Wang, Q. Jia, et al., Chem. Commun. 53 (2017) 5326-5329. doi: 10.1039/C7CC02364B
42. [42]
  L.L. Zhao, Y. Han, C.G. Yan, Chin. Chem. Lett. 31 (2020) 81-83. doi: 10.1016/j.cclet.2019.04.024
43. [43]
  T. Ogawa, N. Usuki, K. Nakazono, Y. Koyama, T. Takata, Chem. Commun. 51 (2015) 5606-5609. doi: 10.1039/C4CC08982K
44. [44]
  T. Takata, ACS Cent. Sci. 6 (2020) 129-143. doi: 10.1021/acscentsci.0c00002
45. [45]
  T. Takata, Bull. Chem. Soc. Jpn. 92 (2019) 409-426. doi: 10.1246/bcsj.20180330
46. [46]
  H. Li, J.N. Zhang, W. Zhou, et al., Org. Lett. 15 (2013) 3070-3073. doi: 10.1021/ol401251u
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