Citation: Shengjie Jiang, Shujuan Zhou, Ying Chen, Hongyu Guo, Fafu Yang. Circularly polarized luminescence based on cholesterol-tetraphenylethylene-perylene liquid crystal[J]. Chinese Chemical Letters, ;2022, 33(5): 2442-2446. doi: 10.1016/j.cclet.2021.10.050 shu

Circularly polarized luminescence based on cholesterol-tetraphenylethylene-perylene liquid crystal

Shengjie Jiang ^{a, b} ,
Shujuan Zhou ^a ,
Ying Chen ^a ,
Hongyu Guo ^{a, b} ,
Fafu Yang ^{a, c, *,}

a.
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007, China
b.
Fujian Key Laboratory of Polymer Materials, Fuzhou 350007, China
c.
Fujian provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, Fuzhou 350007, China

yangfafu@fjnu.edu.cn

Received Date: 8 May 2021
Revised Date: 14 October 2021
Accepted Date: 18 October 2021
Available Online: 23 October 2021

Figures(7)

Perylene derivative with circularly polarized luminescence (CPL) at aggregated state was seldom reported due to the strong ACQ (aggregation-caused quench) effect at aggregation. In this work, a novel cholesterol-tetraphenylethylene-perylene derivative (TPE-P) was designed and synthesized in moderate yield. It exhibited liquid crystalline behavior with orderly hexagonal columnar mesophase and good fluorescence emission at long wavelength (600-700 nm) not only in solution but also at aggregated states based on the AIE (aggregation-induced emission)-FRET (fluorescence resonance energy transfer) effect between tetraphenylethylene unit and perylene moiety. Moreover, the circular dichroism (CD) and CPL studies suggested the effective chiral transfer from cholesterol unit to tetraphenylethylene unit and perylene skeleton due to the spiral liquid crystalline self-assembly. The CD and CPL signals showed the order of THF < THF-hexane < solid film < meosphase, indicating that the higher spiral orderly degree resulted in the stronger chiral transfer. The largest |g_lum| value for mesophase excited at 320 nm was as high as 1.5×10⁻² based on the combining effect of AIE-FRET and chiral transfer. This research not only reported a novel CPL perylene derivative at aggregated state, but also confirmed that the combination of AIE-FRET effect and chiral transfer of liquid crytalline phase was an effective method to construct normal dye with excellent CPL property in aggregated state.
- Tetraphenylethylene,
- Perylene,
- Circularly polarized luminescence,
- Liquid crystal,
- FRET
1. [1]
  Y.J. Zhang, T. Oka, R. Suzuki, J.T. Ye, Science 131 (2014) 725-728.
2. [2]
  R. Carr, N.H. Evans, D. Parker, Chem. Soc. Rev. 41 (2012) 7673-7686. doi: 10.1039/c2cs35242g
3. [3]
  Z.C. Shen, T.Y. Wang, L. Shi, Z.Y. Tang, M.H. Liu, Chem. Sci. 6 (2015) 4267-4272. doi: 10.1039/C5SC01056J
4. [4]
  M. Gong, R. Sawada, Y. Morisaki, Y. Chujo, Macromolecules 50 (2017) 1790-1802. doi: 10.1021/acs.macromol.6b02798
5. [5]
  H.Z. Zheng, W.R. Li, W. Li, X. Wang, et al., Adv. Mater. 30 (2018) 1705948. doi: 10.1002/adma.201705948
6. [6]
  F. Song, Z. Zhao, B.Z. Tang, et al., J. Mater. Chem. C 8 (2020) 3284-3301. doi: 10.1039/C9TC07022B
7. [7]
  M. Li, L.J. Chen, Y. Cai, et al., Chem 5 (2019) 634-648. doi: 10.1016/j.chempr.2018.12.006
8. [8]
  S. Huo, P. Duan, T. Jiao, Q. Peng, M. Liu, Angew. Chem. Int. Ed. 129 (2017) 12342-12346. doi: 10.1002/ange.201706308
9. [9]
  C. Wang, T. Jiang, X. Ma, Chin. Chem. Lett. 31 (2020) 2921-2924. doi: 10.1016/j.cclet.2020.03.021
10. [10]
  D. Zhang, C.Y. Yu, L. Zheng, et al., Chin. Chem. Lett. 31 (2020) 673-676. doi: 10.1016/j.cclet.2019.07.061
11. [11]
  Y.L. Yan, X.L. Li, K.Z. Tang, et al., Chin. Chem. Lett. 32 (2021) 107-112. doi: 10.1016/j.cclet.2020.11.063
12. [12]
  K. Liu, Y.H. Shen, X.J. Li, et al., Chem. Comm. 56 (2020) 12829-12832. doi: 10.1039/D0CC05523A
13. [13]
  S. Jiang, J. Qiu, Y. Chen, H. Guo, F. Yang, Dyes. Pigm. 159 (2018) 533-541. doi: 10.1016/j.dyepig.2018.07.018
14. [14]
  H. Li, J. Cheng, H. Deng, et al., J. Mater. Chem. C 3 (2015) 2399-2404.
15. [15]
  Q. Ye, D. Zhu, H. Zhang, X. Lu, Q. Lu, J. Mater. Chem. C 3 (2015) 6997-7003. doi: 10.1039/C5TC00987A
16. [16]
  S. Chen, S. Jiang, J. Qiu, H. Guo, F. Yang, Chem. Commun. 56 (2020) 7745-7748. doi: 10.1039/C9CC09826G
17. [17]
  F. Song, Z. Xu, Q. Zhang, et al., Adv. Funct. Mater. 28 (2018) 1800051. doi: 10.1002/adfm.201800051
18. [18]
  S. Jiang, J. Qiu, L. Lin, H. Guo, F. Yang, Dyes. Pigm. 163 (2019) 363-370. doi: 10.1016/j.dyepig.2018.12.021
19. [19]
  F. Song, Y. Cheng, Q. Liu, et al., Mater. Chem. Front. 3 (2019) 1768-1778. doi: 10.1039/C9QM00332K
20. [20]
  J. Liu, H. Su, L. Meng, Y, et al., Chem. Sci. 3 (2012) 2737-2747. doi: 10.1039/c2sc20382k
21. [21]
  J.C.Y. Ng, J. Liu, H. Su, et al., J. Mater. Chem. C 2 (2014) 78-83. doi: 10.1039/C3TC31633E
22. [22]
  H. Li, J. Cheng, Y. Zhao, et al., Mater. Horiz. 1 (2014) 518-521. doi: 10.1039/C4MH00078A
23. [23]
  Q. Liu, Q. Xia, S. Wang, B.S. Li, B.Z. Tang, J. Mater. Chem. C 6 (2018) 4807-4816. doi: 10.1039/C8TC00838H
24. [24]
  H. Li, B.S. Li, B.Z. Tang, Chem. Asian J. 14 (2019) 674-688. doi: 10.1002/asia.201801469
25. [25]
  T. Ikeda, T. Masuda, T. Hirao, et al., Chem. Commun. 48 (2012) 6025-6027. doi: 10.1039/c2cc31512b
26. [26]
  F. Würthner, C.R. Saha-Möller, B. Fimmel, et al., Chem. Rev. 116 (2016) 962-1052. doi: 10.1021/acs.chemrev.5b00188
27. [27]
  J. Kumar, T. Nakashima, H. Tsumatori, T. Kawai, J. Phys. Chem. Lett. 5 (2014) 316-321. doi: 10.1021/jz402615n
28. [28]
  T. Kawai, K. Kawamura, H. Tsumatori, et al., ChemPhysChem 8 (2007) 1465-1468. doi: 10.1002/cphc.200600747
29. [29]
  J. Kumar, T. Nakashima, H. Tsumatori, et al., Chem. Eur. J. 19 (2013) 14090-14097. doi: 10.1002/chem.201302146
30. [30]
  H. Tsumatori, T. Nakashima, T. Kawai, Org. Lett. 12 (2010) 2362-2365. doi: 10.1021/ol100701w
31. [31]
  J. Kumar, T. Nakashima, T. Kawai, Langmuir 30 (2014) 6030-6037. doi: 10.1021/la500497g
32. [32]
  J. Kumar, H. Tsumatori, J. Yuasa, T. Kawai, T. Nakashima, Angew. Chem. Int. Ed. 54 (2015) 5943-5947. doi: 10.1002/anie.201500292
33. [33]
  J. Li, C. Yang, X. Peng, et al., Org. Biomol. Chem. 15 (2017) 8463-8471. doi: 10.1039/C7OB01959A
34. [34]
  F. Li, Y. Li, G. Wei, et al., Chem. Eur. J. 22 (2016) 12910-12915. doi: 10.1002/chem.201601328
35. [35]
  B. Li, W. Peng, S. Luo, et al., Org. Lett. 21 (2019) 1417-1421. doi: 10.1021/acs.orglett.9b00152
36. [36]
  P. Reine, A.M. Ortuño, I.F.A. Mariz, D. Miguel, et al., Front. Chem. 8 (2020) 306-312. doi: 10.3389/fchem.2020.00306
37. [37]
  B. Liu, M. Böckmann, W. Jiang, N.L. Doltsinis, Z. Wang, J. Am. Chem. Soc. 142 (2020) 7092-7099. doi: 10.1021/jacs.0c00954
38. [38]
  J. Li, J. Wang, H. Li, et al., Chem. Soc. Rev. 49 (2020) 1144-1172. doi: 10.1039/C9CS00495E
39. [39]
  Z. Zhao, H. Zhang, J.W.Y. Lam, B.Z. Tang, Angew. Chem. Int. Ed. 59 (2020) 9888-9907. doi: 10.1002/anie.201916729
40. [40]
  H.T. Feng, J.W.Y. Lam, B.Z. Tang, Coord. Chem. Rev. 406 (2020) 213142. doi: 10.1016/j.ccr.2019.213142
41. [41]
  Zhu M, Zhuo Y, Cai K, Guo H, F. Yang, Dyes Pigm. 147 (2017) 343-349. doi: 10.1016/j.dyepig.2017.08.027
42. [42]
  M. Zhu, Y. Chen, X. Zhang, et al., Soft. Matter. 14 (2018) 6737-6744. doi: 10.1039/C8SM01183D
43. [43]
  L. Lu, H.J. Sun, Y.T. Zeng, Y. Shao, et al., J. Mater. Chem. C 8 (2020) 10422-10430. doi: 10.1039/C9TC05792G
44. [44]
  V. Grande, B Soberats, Herbst S, V. Stepanenko, F. Würthner, Chem. Sci. 9 (2018) 6904-6911. doi: 10.1039/C8SC02409J
45. [45]
  S.C. Tan, J.Y. Tao, W.L. Luo, et al., Chin. Chem. Lett. 32 (2021) 1149-1152. doi: 10.1016/j.cclet.2020.09.016
46. [46]
  L. Meng, Q. Wu, F. Yang, H. Guo, New J. Chem. 39 (2015) 72-76. doi: 10.1039/C4NJ00993B
47. [47]
  Q. Wei, L. Shi, H. Cao, et al., Chin. Chem. Lett. 18 (2007) 527-529. doi: 10.1016/j.cclet.2007.03.008
48. [48]
  C. Keum, D. Becker, E. Archer, et al., Adv. Optical Mater. 8 (2020) 2000414. doi: 10.1002/adom.202000414
49. [49]
  M. Zhu, Z. Wang, F. Yang, H. Guo, Dyes Pigm. 133 (2016) 387-394. doi: 10.1016/j.dyepig.2016.06.021
50. [50]
  R.K. Gupta, A.A. Sudhakar, Langmuir 35 (2019) 2455-2479. doi: 10.1021/acs.langmuir.8b01081
51. [51]
  M. Zhu, H. Guo, F. Yang, Z. Wang, Rsc. Adv. 7 (2017) 4320-4328. doi: 10.1039/C6RA27003D
52. [52]
  Y.Z. Zhao, D. Wang, Z.M. He, et al., Chin. Chem. Lett. 26 (2015) 185-789.
53. [53]
  F. Würthner, C.R. Saha-Möller, B. Fimmel, et al., Chem. Rev. 116 (2016) 962-1052. doi: 10.1021/acs.chemrev.5b00188
54. [54]
  J. Lin, X. Ji, H. Guo, F. Yang, J. Mol. Liq. 290 (2019) 111228. doi: 10.1016/j.molliq.2019.111228
55. [55]
  X. Zhang, H. Guo, F. Yang, J. Yuan, Tetrahedron Lett. 57 (2016) 905-909. doi: 10.1016/j.tetlet.2016.01.047
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