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
1. [1]
  Yang Li , Yihan Chen , Jiaxin Luo , Qihuan Li , Yiwu Quan , Yixiang Cheng . Enhanced circularly polarized luminescence emission promoted by achiral dichroic oligomers of F8BT in cholesteric liquid crystal. Chinese Chemical Letters, 2024, 35(11): 109864-. doi: 10.1016/j.cclet.2024.109864
2. [2]
  Yuanpeng Ye , Longfei Yao , Guofeng Liu . Engineering circularly polarized luminescence through symmetry manipulation in achiral tetraphenylpyrazine structures. Chinese Journal of Structural Chemistry, 2025, 44(2): 100460-100460. doi: 10.1016/j.cjsc.2024.100460
3. [3]
  Zhao-Xia Lian , Xue-Zhi Wang , Chuang-Wei Zhou , Jiayu Li , Ming-De Li , Xiao-Ping Zhou , Dan Li . Producing circularly polarized luminescence by radiative energy transfer from achiral metal-organic cage to chiral organic molecules. Chinese Chemical Letters, 2024, 35(8): 109063-. doi: 10.1016/j.cclet.2023.109063
4. [4]
  Yongjing Deng , Feiyang Li , Zijian Zhou , Mengzhu Wang , Yongkang Zhu , Jianwei Zhao , Shujuan Liu , Qiang Zhao . Chiral induction and Sb³⁺ doping in indium halides to trigger second harmonic generation and circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(8): 109085-. doi: 10.1016/j.cclet.2023.109085
5. [5]
  Xue-Zhi Wang , Yi-Tong Liu , Chuang-Wei Zhou , Bei Wang , Dong Luo , Mo Xie , Meng-Ying Sun , Yong-Liang Huang , Jie Luo , Yan Wu , Shuixing Zhang , Xiao-Ping Zhou , Dan Li . Amplified circularly polarized luminescence of chiral metal-organic frameworks via post-synthetic installing pillars. Chinese Chemical Letters, 2024, 35(10): 109380-. doi: 10.1016/j.cclet.2023.109380
6. [6]
  Xiang Wang , Qingping Song , Zixiang He , Gong Zhang , Tengfei Miao , Xiaoxiao Cheng , Wei Zhang . Constructing diverse switchable circularly polarized luminescence via a single azobenzene polymer film. Chinese Chemical Letters, 2025, 36(1): 110047-. doi: 10.1016/j.cclet.2024.110047
7. [7]
  Chunyu Yan , Qinglong Qiao , Wei Zhou , Xuelian Zhou , Yonghui Chen , Lu Miao , Zhaochao Xu . FRET-based in vitro assay for rapid detecting of SARS-CoV-2 entry inhibitors. Chinese Chemical Letters, 2025, 36(5): 110258-. doi: 10.1016/j.cclet.2024.110258
8. [8]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
9. [9]
  Wenying Cui , Zhetong Jin , Wentao Fu , Chengshuo Shen . Flag-hinge-like highly luminescent chiral nanographenes with twist geometry. Chinese Chemical Letters, 2024, 35(11): 109667-. doi: 10.1016/j.cclet.2024.109667
10. [10]
  Fengying Ye , Ming Hu , Jun Luo , Wei Yu , Zhirong Xu , Jinjin Fu , Yansong Zheng . Significantly boosting circularly polarized luminescence by synergy of helical and planar chirality. Chinese Chemical Letters, 2025, 36(5): 110724-. doi: 10.1016/j.cclet.2024.110724
11. [11]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
12. [12]
  Jiawei Li , Cheng Chen , Mingyan Wu . Donor-acceptor type organic cocrystals for deep-red circularly polarized luminescence and two-photon excited emission. Chinese Journal of Structural Chemistry, 2025, 44(3): 100513-100513. doi: 10.1016/j.cjsc.2025.100513
13. [13]
  Wenkai Chen , Yunjia Shen , Xiangmeng Kong , Yanli Zeng . Quantum Chemistry Calculation of Key Physical Quantity in Circularly Polarized Luminescence: Introducing an Exploratory Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 83-91. doi: 10.12461/PKU.DXHX202405018
14. [14]
  Wenzhong Zhang , Zirui Yan , Lingcheng Chen , Yi Xiao . Sn-fused perylene diimides: Synthesis, mechanism, and properties. Chinese Chemical Letters, 2024, 35(10): 109582-. doi: 10.1016/j.cclet.2024.109582
15. [15]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
16. [16]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
17. [17]
  Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
18. [18]
  Wenbin Zhou , Yafei Gao , Xinyu Feng , Yanqing Zhang , Cong Yang , Lanxi He , Fenghe Zhang , Xiaoguang Li , Qing Li . Biomimetic nanoplatform integrates FRET-enhanced photodynamic therapy and chemotherapy for cascaded revitalization of the tumor immune microenvironment in OSCC. Chinese Chemical Letters, 2025, 36(1): 109763-. doi: 10.1016/j.cclet.2024.109763
19. [19]
  Yukun CHEN , Kexin FENG , Bolun ZHANG , Wentao SONG , Jianjun ZHANG . Syntheses, crystal structures, and diametrically opposed mechanically-stimulated luminescence response of two Mg(Ⅱ) metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1227-1234. doi: 10.11862/CJIC.20240448
20. [20]
  Kexiang Zhao , Zongrui Wang , Qi-Yuan Wan , Jing-Cai Zeng , Li Ding , Jie-Yu Wang , Jian Pei . Janus-type BN-embedded perylene diimides via a "shuffling" strategy: Regioselective functionalizable building block towards high-performance n-type organic semiconductors. Chinese Chemical Letters, 2025, 36(6): 110339-. doi: 10.1016/j.cclet.2024.110339

Get Citation

PDF

XML

Metrics

PDF Downloads(15)
Abstract views(966)
HTML views(105)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142