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
1. [1]
  Yiming Yang , Lichao Sun , Qingfeng Zhang . Plasmonic nanocrystals with intrinsic chirality: Biomolecule-directed synthesis and applications. Chinese Journal of Structural Chemistry, 2025, 44(1): 100467-100467. doi: 10.1016/j.cjsc.2024.100467
2. [2]
  Shuwen Guo , Haipeng Xu , Zijun Cheng , Leyong Wang , Peng Yang , Ruibing Wang . Efficient cytosolic delivery of protein by preorganized amidiniums on pillar[5]arene. Chinese Chemical Letters, 2025, 36(10): 111022-. doi: 10.1016/j.cclet.2025.111022
3. [3]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
4. [4]
  Cui-Ting Yang , Dan-Dan Wang , Shuai Chen , Jian-Mei Yang , Jun-Nan He , Jun-Hui Zhang , Xiao-Qing Liu , Jin Zhang , Lei Zhang , Yan Zhao . A chiral supramolecular nanocatcher prepared by d-biotin-pillar[5]arene for the selective capture and targeted delivery of oxaliplatin enantiomers. Chinese Chemical Letters, 2025, 36(9): 110820-. doi: 10.1016/j.cclet.2025.110820
5. [5]
  Kai Zhu , Lei Yang , Yang Yang , Yanqi Wu , Fengzhi Zhang . Recent advances toward the catalytic enantioselective synthesis of planar chiral cyclophanes. Chinese Chemical Letters, 2025, 36(7): 110678-. doi: 10.1016/j.cclet.2024.110678
6. [6]
  Jun-Yi Wang , Jue-Yu Bao , Zheng-Guang Wu , Zheng-Yin Du , Xunwen Xiao , Xu-Feng Luo . Recent progress in steric modulation of MR-TADF materials and doping concentration independent OLEDs with narrowband emission. Chinese Journal of Structural Chemistry, 2025, 44(1): 100451-100451. doi: 10.1016/j.cjsc.2024.100451
7. [7]
  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
8. [8]
  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
9. [9]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281
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]
  Jieqiong Xu , Wenbin Chen , Shengkai Li , Qian Chen , Tao Wang , Yadong Shi , Shengyong Deng , Mingde Li , Peifa Wei , Zhuo Chen . Organic stoichiometric cocrystals with a subtle balance of charge-transfer degree and molecular stacking towards high-efficiency NIR photothermal conversion. Chinese Chemical Letters, 2024, 35(10): 109808-. doi: 10.1016/j.cclet.2024.109808
12. [12]
  Jingyu Chen , Sha Wu , Yuhao Wang , Jiong Zhou . Near-perfect separation of alicyclic ketones and alicyclic alcohols by nonporous adaptive crystals of perethylated pillar[5]arene and pillar[6]arene. Chinese Chemical Letters, 2025, 36(4): 110102-. doi: 10.1016/j.cclet.2024.110102
13. [13]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
14. [14]
  Lintao Wu , Yujia Meng , Xumei Zheng , Yiqiao Bai , Chun Han , Zhijun Wang , Jie Yang , Xiaobi Jing , Yong Yao . Pillar[5]arene based prodrug as a GSH-responsive SO₂ nanogenerator for effective gas cancer therapy. Chinese Chemical Letters, 2025, 36(9): 110808-. doi: 10.1016/j.cclet.2024.110808
15. [15]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
16. [16]
  Qianyun Ye , Yuanyuan Liang , Yuhe Yuan , Xiaohuan Sun , Liqi Zhu , Xuan Wu , Jie Han , Rong Guo . pH-responsive chiral supramolecular cysteine-Zn²⁺-indocyanine green assemblies for triple-level chirality-specific anti-tumor efficacy. Chinese Chemical Letters, 2025, 36(5): 110432-. doi: 10.1016/j.cclet.2024.110432
17. [17]
  Jiayao Li , Xinru Peng , Shiwei Yin , Changwei Wang , Yirong Mo . Metastability of π-π stacking between the closed-shell ions of like charges. Chinese Journal of Structural Chemistry, 2024, 43(5): 100213-100213. doi: 10.1016/j.cjsc.2023.100213
18. [18]
  Jing Guo . Stacking solid-state electrolyte and aluminum pellets for anode-free solid-state batteries. Chinese Chemical Letters, 2025, 36(5): 110764-. doi: 10.1016/j.cclet.2024.110764
19. [19]
  Jingxiong Jiang , Yao Dong , Yuchun Wang , Lijuan Qi , Zhen-Yu Li , Tai-Bao Wei , Wen-Juan Qu , Qi Lin , Bingbing Shi . Separation of toluene-alcohol azeotropes by porous crystals of fluorinated leaning pillar[6]arene. Chinese Chemical Letters, 2025, 36(8): 110759-. doi: 10.1016/j.cclet.2024.110759
20. [20]
  Kun Zhang , Xin-Yue Lou , Yan Wang , Weiwei Huan , Ying-Wei Yang . Emission enhancement induced by the supramolecular assembly of leggero pillar[5]arenes for the detection and separation of silver ions. Chinese Chemical Letters, 2025, 36(6): 110464-. doi: 10.1016/j.cclet.2024.110464

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(21)
HTML views(3)

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