Citation: Xintian Qu, Zeen Liu, Zhifan Wang, Dongyan Yu, Xueqiu Huang, Jie Yang, Jiecheng Ji, Xueqin Wei, Cheng Yang. Achieving strong and tunable circularly polarized luminescence through pillar[5]arenes insertion in BINOL-Py-based chromophore[J]. Chinese Chemical Letters, ;2025, 36(11): 111024. doi: 10.1016/j.cclet.2025.111024 shu

Achieving strong and tunable circularly polarized luminescence through pillar[5]arenes insertion in BINOL-Py-based chromophore

Xintian Qu ^{a, 1} ,
Zeen Liu ^{a, 1} ,
Zhifan Wang ^b ,
Dongyan Yu ^a ,
Xueqiu Huang ^a ,
Jie Yang ^a ,
Jiecheng Ji ^{b, *,} ,
Xueqin Wei ^{a, *,} ,
Cheng Yang ^b

a.
Guangxi Key Laboratory of Pharmaceutical Precision Detection and Screening, Guangxi Key Laboratory of Bioactive Molecules Research and Evaluation, and Key Laboratory of Micro-Nanoscale Bioanalysis and Drug Screening of Guangxi Education Department, Pharmaceutical College, Guangxi Medical University, Nanning 530021, China
b.
Laboratory of Precision Therapeutics, West China Hospital, College of Chemistry, Sichuan University, Chengdu 610041, China

jijiecheng_scu@163.com

weixueqin@gxmu.edu.cn

Received Date: 5 December 2024
Revised Date: 25 February 2025
Accepted Date: 2 March 2025
Available Online: 3 March 2025

Figures(5)

A series of [1, 1′-binaphthalene]-2, 2′-diol-pyrene (BINOL-Py) functionalized pillar[5]arenes with different spacer lengths were synthesized and separated by chiral HPLC to obtain their enantiomers. We elucidated the synergistic effect of the planar chirality of pillar[5]arenes and axial chirality of BINOL on the circularly polarized luminescence (CPL) behaviors of hybrid chiral BINOL-Py functionalized pillar[5]arenes, achieving high g_lum up to 1.7 × 10^–2. In addition, ascribed to the regulation of chirality information transmission through planar chirality of pillar[5]arenes, the resolved BINOL-Py functionalized pillar[5]arenes reveal unique tunable circular dichroism (CD) and CPL in different aggregation state and upon the addition of guest, providing not only a novel design strategy for developing molecular systems with chiroptical tunability but also an intriguing platform for the construction of CPL luminescent materials based on chiral macrocycles.
- CPL,
- Pillar[5]arene,
- Planar chirality,
- Chirality transfer,
- π-π stacking
1. [1]
  M. Liu, L. Zhang, T. Wang, Chem. Rev. 115 (2015) 7304–7397. doi: 10.1021/cr500671p
2. [2]
  P. Chen, C. Yu, J. Chen, et al., Chin. Chem. Lett. 34 (2023) 108627.
3. [3]
  H. Kuang, C. Xu, Z. Tang, Adv. Mater. 32 (2020) 2005110.
4. [4]
  M. Hu, H.T. Feng, Y.X. Yuan, et al., Coord. Chem. Rev. 416 (2020) 213329.
5. [5]
  W. Chen, B. Li, G. Gao, et al., Interdiscip. Mater. 2 (2023) 689–713. doi: 10.1002/idm2.12117
6. [6]
  H. Chang, R. Qiao, C. Li, Chin. Chem. Lett. 36 (2025) 110675. doi: 10.1016/j.cclet.2024.110675
7. [7]
  F. Zinna, U. Giovanella, L.D. Bari, Adv. Mater. 27 (2015) 1791–1795. doi: 10.1002/adma.201404891
8. [8]
  K. Takaishi, M. Yasui, T. Ema, J. Am. Chem. Soc. 140 (2018) 5334–5338. doi: 10.1021/jacs.8b01860
9. [9]
  X. Feng, W. Meng, H. Du, Chem. Soc. Rev. 52 (2023) 8580–8598. doi: 10.1039/d3cs00701d
10. [10]
  T. Li, X. Zhu, G. Ouyang, et al., Mater. Chem. Front. 7 (2023) 3879–3903. doi: 10.1039/d3qm00339f
11. [11]
  J.Q. Wang, X.N. Han, Y. Han, et al., Chem. Commun. 59 (2023) 13089–13106. doi: 10.1039/d3cc04187e
12. [12]
  S. Yang, S. Zhang, F. Hu, et al., Coord. Chem. Rev. 485 (2023) 215116.
13. [13]
  P. Fan, Z. Fang, S. Wang, et al., Chin. Chem. Lett. 34 (2023) 107934.
14. [14]
  D. Cappelletti, M. Barbieri, A. Aliprandi, et al., Nanoscale 16 (2024) 9153–9168. doi: 10.1039/d4nr00383g
15. [15]
  L. Zhang, Y. Xu, W. Wei, Chem. Commun. 59 (2023) 13562–13570. doi: 10.1039/d3cc04159j
16. [16]
  Y. Xia, M. Chen, S. Li, et al., J. Mater. Chem. C 10 (2022) 12332–12337. doi: 10.1039/d2tc00481j
17. [17]
  Y. Zuo, X. Liu, E. Fu, et al., Angew. Chem. Int. Ed. 62 (2023) e202217225.
18. [18]
  W. Yuan, C. Wang, M. Wu, et al., Macromolecules 54 (2021) 7291–7297. doi: 10.1021/acs.macromol.1c00631
19. [19]
  Z. Geng, Z. Wang, S.E. Zhu, et al., J. Colloid Interface Sci. 669 (2024) 561–568.
20. [20]
  H. Kashida, K. Nishikawa, Y. Ito, et al., Chem. Eur. J. 27 (2021) 14582–14585. doi: 10.1002/chem.202102333
21. [21]
  M.X. Sun, C.Z. Ni, F.Q. Zhang, et al., Chin. Chem. Lett. 34 (2023) 108345.
22. [22]
  M. Hasegawa, Y. Nojima, Y. Mazaki, ChemPhotoChem 5 (2021) 1042–1058. doi: 10.1002/cptc.202100162
23. [23]
  G. Albano, G. Pescitelli, L. Di Bari, Chem. Rev. 120 (2020) 10145–10243. doi: 10.1021/acs.chemrev.0c00195
24. [24]
  R. Fu, Q.Y. Zhao, H. Han, et al., Angew. Chem. Int. Ed. 62 (2023) e202315990.
25. [25]
  K. Adachi, S. Fa, K. Wada, et al., J. Am. Chem. Soc. 145 (2023) 8114–8121. doi: 10.1021/jacs.3c01019
26. [26]
  S. Fa, T. Tomita, K. Wada, et al., Chem. Sci. 13 (2022) 5846–5853. doi: 10.1039/d2sc00952h
27. [27]
  C. Tu, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 61 (2022) e202203541.
28. [28]
  T. Ogoshi, S. Kanai, S. Fujinami, et al., J. Am. Chem. Soc. 130 (2008) 5022–5023. doi: 10.1021/ja711260m
29. [29]
  T. Ogoshi, K. Masaki, R. Shiga, et al., Org. Lett. 13 (2011) 1264–1266. doi: 10.1021/ol200062j
30. [30]
  T. Ogoshi, D. Yamafuji, T. Akutsu, et al., Chem. Commun. 49 (2013) 8782–8784. doi: 10.1039/c3cc44672g
31. [31]
  T.F. Al-Azemi, M. Vinodh, F.H. Alipour, et al., Org. Chem. Front. 6 (2019) 603–610. doi: 10.1039/c8qo01343h
32. [32]
  J.F. Chen, J.D. Ding, T.B. Wei, Chem. Commun. 57 (2021) 9029–9039. doi: 10.1039/d1cc03778a
33. [33]
  Y. Lv, C. Xiao, J. Ma, et al., Chin. Chem. Lett. 35 (2024) 108757.
34. [34]
  J.F. Chen, X. Yin, B. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 11267–11272. doi: 10.1002/anie.202001145
35. [35]
  F. Zhao, J. Zhao, H. Liu, et al., J. Am. Chem. Soc. 145 (2023) 10092–10103. doi: 10.1021/jacs.3c00306
36. [36]
  J. Han, S. Guo, H. Lu, et al., Adv. Opt. Mater. 6 (2018) 1800538.
37. [37]
  K. Kato, S. Ohtani, M. Gon, et al., Chem. Sci. 13 (2022) 13147–13152. doi: 10.1039/d2sc04168e
38. [38]
  K. Wada, T. Ogoshi, Mater. Chem. Front. 8 (2024) 1212–1229. doi: 10.1039/d3qm01176c
39. [39]
  K. Kato, Y. Kurakake, S. Ohtani, et al., Angew. Chem. Int. Ed. 61 (2022) e202209222.
40. [40]
  T. Zhao, W. Wu, C. Yang, Chem. Commun. 59 (2023) 11469–11483. doi: 10.1039/d3cc03829g
41. [41]
  J. Yao, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 56 (2017) 6869–6873. doi: 10.1002/anie.201702542
42. [42]
  K. Diao, C. Ruan, R. Wang, et al., Tetrahedron Lett. 137 (2024) 154941.
43. [43]
  J.L. Song, C. Chen, X. Li, et al., Nat. Commun. 15 (2024) 10531.
44. [44]
  X. Li, W.T. Xu, X.Q. Xu, et al., Angew. Chem. Int. Ed. 64 (2025) e202412548.
45. [45]
  H. Tanaka, Y. Inoue, T. Mori, ChemPhotoChem 2 (2018) 386–402. doi: 10.1002/cptc.201800015
46. [46]
  L. Arrico, L. Di Bari, F. Zinna, Chem. Eur. J. 27 (2021) 2920–2934. doi: 10.1002/chem.202002791
47. [47]
  J. Ji, X. Wei, W. Wu, et al., J. Am. Chem. Soc. 144 (2022) 1455–1463. doi: 10.1021/jacs.1c13210
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