Citation: Hong Yang, Mengqi Li, Weijun Zhao, Zhiqian Guo, Wei-Hong Zhu. Photoresponsive aggregation-induced emission polymer film for anti-counterfeiting[J]. Chinese Chemical Letters, ;2021, 32(12): 3882-3885. doi: 10.1016/j.cclet.2021.05.053 shu

Photoresponsive aggregation-induced emission polymer film for anti-counterfeiting

Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China

zhwj@ecust.edu.cn

Received Date: 12 April 2021
Revised Date: 20 May 2021
Accepted Date: 24 May 2021
Available Online: 31 May 2021

Figures(4)

The development of solid-state smart materials, in particular those showing photoresponsive luminescence, is highly desirable for their cutting edge applications in displays, sensors, data-storage, and anti-counterfeiting. However, to achieve both excellent photoresponsive performance and bright luminescence in solid state remains challenge. Herein, we integrate a novel photochromic fluorophore YL into flexible polymer chains, thereby enabling the resultant polymer PYL with reversible photoisomerization upon aggregation. Remarkably, the polymer PYL possesses excellent photochromic properties and aggregation-induced emission (AIE) activity, which can be attributed to the photoactive YL moiety. Upon light exposure, its film exhibits reversibly off-to-on fluorescent modulation with quick response, high emission efficiency and signal contrast, sharply different from the weak emission in solution. The novel photoresponsive AIE polymer with invisible/visible color and fluorescence transformation allows for advanced anti-counterfeiting applications. This work provides an efficient platform for constructing solid-state photocontrollable luminescent materials.
- Aggregation-induced emission,
- Photoresponsive luminescence,
- Diarylethene,
- Photochromism,
- Polymer film,
- Anti-counterfeiting
1. [1]
  T. Grotjohann, I. Testa, M. Leutenegger, et al., Nature 478(2011) 204-208. doi: 10.1038/nature10497
2. [2]
  D. Okada, Z.H. Lin, J.S. Huang, et al., Mater. Horiz. 7(2020) 1801-1808. doi: 10.1039/D0MH00566E
3. [3]
  J. Liang, M. Chu, Z. Zhou, et al., Nano Lett. 20(2020) 7116-7122. doi: 10.1021/acs.nanolett.0c02378
4. [4]
  J. Dong, K. Zhang, X. Li, et al., Nat. Commun. 8(2017) 1142. doi: 10.1038/s41467-017-01293-x
5. [5]
  Y. Yang, S. Zhang, X. Zhang, et al., Nat. Commun. 10(2019) 3165. doi: 10.1038/s41467-019-11144-6
6. [6]
  X. Jiang, H. Gao, X. Zhang, et al., Nat. Commun. 9(2018) 3799. doi: 10.1038/s41467-018-06101-8
7. [7]
  D. Kim, K. Jeong, J.E. Kwon, et al., Nat. Commun. 10(2019) 3089. doi: 10.1038/s41467-019-10986-4
8. [8]
  L. Zong, H. Zhang, Y. Li, et al., ACS Nano 12(2018) 9532-9540. doi: 10.1021/acsnano.8b05090
9. [9]
  H. Wu, Z. Chen, W. Chi, et al., Angew. Chem. Int. Ed. 58(2019) 11419-11423. doi: 10.1002/anie.201906507
10. [10]
  Z. Li, X. Liu, G. Wang, et al., Nat. Commun. 12(2021) 1363. doi: 10.1038/s41467-021-21677-4
11. [11]
  Y. He, J. Li, J. Li, et al., ACS Appl. Polym. Mater. 1(2019) 746-754. doi: 10.1021/acsapm.8b00276
12. [12]
  Z. Li, G. Wang, Y. Ye, et al., Angew. Chem. Int. Ed. 58(2019) 18025-18031. doi: 10.1002/anie.201910467
13. [13]
  P. Wei, J.X. Zhang, Z. Zhao, et al., J. Am. Chem. Soc. 140(2018) 1966-1975. doi: 10.1021/jacs.7b13364
14. [14]
  D. Kim, J.E. Kwon, S.Y. Park, Adv. Funct. Mater. 28(2018) 1706213. doi: 10.1002/adfm.201706213
15. [15]
  F.D. Jochum, P. Theato, Chem. Soc. Rev. 42(2013) 7468-7483. doi: 10.1039/C2CS35191A
16. [16]
  K. Uno, M.L. Bossi, M. Irie, et al., J. Am. Chem. Soc. 141(2019) 16471-16478. doi: 10.1021/jacs.9b08748
17. [17]
  G. Naren, C.W. Hsu, S. Li, et al., Nat. Commun. 10(2019) 3996. doi: 10.1038/s41467-019-11885-4
18. [18]
  J. Zhang, Y. Fu, H.H. Han, et al., Nat. Commun. 8(2017) 987. doi: 10.1038/s41467-017-01137-8
19. [19]
  Y. Takagi, T. Kunishi, T. Katayama, et al., Photochem. Photobiol. Sci. 11(2012) 1661. doi: 10.1039/c2pp25078k
20. [20]
  X. Wu, Z. Zhang, H. Liu, S. Pu, RSC Adv. 10(2020) 15547-15553. doi: 10.1039/C9RA10907B
21. [21]
  S. Tang, F. Song, M. Lu, et al., Sci. China Chem. 62(2019) 451-459.
22. [22]
  Z. Xu, Q.T. Liu, X. Wang, et al., Chem. Sci. 11(2020) 2729-2734. doi: 10.1039/C9SC05697A
23. [23]
  M. Irie, T. Fukaminato, K. Matsuda, S. Kobatake, Chem. Rev. 114(2014) 12174-12277.
24. [24]
  C. Li, H. Yan, L.X. Zhao, et al., Nat. Commun. 5(2014) 5709. doi: 10.1038/ncomms6709
25. [25]
  T. Fukaminato, T. Doi, N. Tamaoki, et al., J. Am. Chem. Soc. 133(2011) 4984-4990. doi: 10.1021/ja110686t
26. [26]
  J.W. Chung, S.J. Yoon, S.J. Lim, et al., Angew. Chem. Int. Ed. 48(2009) 7030-7034. doi: 10.1002/anie.200902777
27. [27]
  X. Zhang, D. Görl, V. Stepanenko, F. Würthner, Angew. Chem. Int. Ed. 53(2014) 1270-1274. doi: 10.1002/anie.201308963
28. [28]
  L. Ma, C. Li, Q. Yan, et al., Chin. Chem. Lett. 31(2020) 361-364. doi: 10.1016/j.cclet.2019.07.040
29. [29]
  H. Yang, M. Li, C. Li, et al., Angew. Chem. Int. Ed. 59(2020) 8560-8570. doi: 10.1002/anie.201909830
30. [30]
  G. Liu, S. Pu, R. Wang, Org. Lett. 15(2013) 980-983. doi: 10.1021/ol400188h
31. [31]
  H. Nie, J.L. Self, A.S. Kuenstler, et al., Adv. Opt. Mater. 7(2019) 1900224. doi: 10.1002/adom.201900224
32. [32]
  Z. Wang, Z. Ma, Y. Wang, et al., Adv. Mater. 27(2015) 6469-6474. doi: 10.1002/adma.201503424
33. [33]
  Y. Gu, E.A. Alt, H. Wang, et al., Nature 560(2018) 65-69. doi: 10.1038/s41586-018-0339-0
34. [34]
  S. Jiang, L. Meng, W. Ma, et al., Chin. Chem. Lett. 32(2021) 1037-1040. doi: 10.1016/j.cclet.2020.09.019
35. [35]
  W. Li, C. Jiao, X. Li, et al., Angew. Chem. Int. Ed. 53(2014) 4603-4607. doi: 10.1002/anie.201310438
36. [36]
  H. Zhou, F. Liu, X. Wang, et al., J. Mater. Chem. C 3(2015) 5490-5498. doi: 10.1039/C5TC00752F
37. [37]
  J. Yang, K. Gu, C. Shi, et al., Mater. Chem. Front. 3(2019) 1503-1509. doi: 10.1039/C9QM00147F
38. [38]
  M. Irie, Chem. Rev. 100(2000) 1685-1716. doi: 10.1021/cr980069d
39. [39]
  S. Nakamura, M. Irie, J. Org. Chem. 53(1988) 6136-6138. doi: 10.1021/jo00261a035
40. [40]
  T. Morozumi, T. Anada, H. Nakamura, J. Phys. Chem. B 105(2001) 2923-2931. doi: 10.1021/jp0030600
41. [41]
  Y. Hong, J.W.Y. Lam, B.Z. Tang, Chem. Commun. (2009) 4332-4353.
42. [42]
  L. Meng, X. Ma, S. Jiang, et al., CCS Chem. 3(2021) 2084-2094. doi: 10.31635/ccschem.020.202000420
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