Citation: Luyao Wang, Mengqi Pei, Dongdong Sun, Jingjing Liu, Xie Han, Simin Liu. Synergistically enhancing mechanochromism of carbazole derivatives via crystallization and host-guest complexation[J]. Chinese Chemical Letters, ;2026, 37(9): 112221. doi: 10.1016/j.cclet.2025.112221 shu

Synergistically enhancing mechanochromism of carbazole derivatives via crystallization and host-guest complexation

Luyao Wang ^{a, 1} ,
Mengqi Pei ^{a, 1} ,
Dongdong Sun ^a ,
Jingjing Liu ^a ,
Xie Han ^{a, b, *,} ,
Simin Liu ^{a, b, *,}

a.
School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, China
b.
The State Key Laboratory of Refractories and Metallurgy, Institute of Advanced Materials and Nanotechnology, Wuhan University of Science and Technology, Wuhan 430081, China

hanxie@wust.edu.cn

liusimin@wust.edu.cn

Received Date: 13 July 2025
Revised Date: 23 November 2025
Accepted Date: 5 December 2025
Available Online: 6 December 2025

Figures(5)

Constructing high-contrast mechanochromic luminescent (MCL) materials with a wide range of emission color variations remains challenging. Herein, a host-guest strategy is proposed to optimize molecular MCL behavior. Two pyridinium-functionalized carbazole derivatives only exhibit a slight red-shifted fluorescence under mechanical stimulation. By forming host-guest complexes with cucurbit[n]urils (CB[n]s, n = 8 or 10), the complexes demonstrate more significant fluorescence wavelength changes after grinding. Mechanistic studies reveal that the crystallization and CB[n]’s confinement effect, synergistically induce more twisted molecular conformations and facilitate the planarization of guests under mechanical stimulation. Moreover, the host-guest complexes also exhibit outstanding MCL property in the polyvinyl alcohol (PVA) film. This strategy is both conceptually and synthetically simple and provides a promising method for preparing high-contrast MCL materials.
- Cucurbit[n]urils,
- Mechanochromic luminescent,
- Confinement effect,
- Crystallization,
- Carbazole derivatives
1. [1]
  F. Ciardelli, G. Ruggeri, A. Pucci, Chem. Soc. Rev. 42 (2013) 857–870. doi: 10.1039/C2CS35414D
2. [2]
  Z. Chi, X. Zhang, B. Xu, et al., Chem. Soc. Rev. 41 (2012) 3878–3896. doi: 10.1039/c2cs35016e
3. [3]
  H. Sun, S. Liu, W. Lin, et al., Nat. Commun. 5 (2014) 3601. doi: 10.1038/ncomms4601
4. [4]
  Z. Ma, Z. Wang, M. Teng, et al., ChemPhysChem 16 (2015) 1811–1828. doi: 10.1002/cphc.201500181
5. [5]
  Y. Sagara, S. Yamane, M. Mitani, et al., Adv. Mater. 28 (2015) 1073–1095.
6. [6]
  P. Xue, J. Ding, P. Wang, et al., J. Mater. Chem. C 4 (2016) 6688–6706. doi: 10.1039/C6TC01503D
7. [7]
  K. Wang, L. Wan, J. Wang, et al., Chin. Chem. Lett. 35 (2024) 109554. doi: 10.1016/j.cclet.2024.109554
8. [8]
  Q. Li, Z. Li, Acc. Chem. Res. 53 (2020) 962–973. doi: 10.1021/acs.accounts.0c00060
9. [9]
  J. Zhang, M. Zhu, Y. Lu, et al., Chem. Eur. J. 28 (2022) e202200458. doi: 10.1002/chem.202200458
10. [10]
  W. Wang, R. Li, S. Xiao, et al., CCS Chem. 4 (2022) 899–909. doi: 10.31635/ccschem.021.202100885
11. [11]
  Z. Lv, Z. Man, Z. Xu, et al., Adv. Opt. Mater. 9 (2021) 2100598. doi: 10.1002/adom.202100598
12. [12]
  C. Zhu, Q. Luo, Y. Shen, et al., Angew. Chem. Int. Ed. 60 (2021) 8510–8514. doi: 10.1002/anie.202100301
13. [13]
  W.Z. Yuan, Y. Tan, Y. Gong, et al., Adv. Mater. 25 (2013) 2837–2843. doi: 10.1002/adma.201205043
14. [14]
  W. Guo, M. Wang, L. Si, et al., Chem. Sci. 14 (2023) 6348–6354. doi: 10.1039/D3SC01730C
15. [15]
  T. Jadhav, B. Dhokale, R. Misra, J. Mater. Chem. C 3 (2015) 9063–9068. doi: 10.1039/C5TC01871D
16. [16]
  K. Zheng, H. Chen, Y. Xiao, et al., Chem. Eur. J. 27 (2021) 14964–14970. doi: 10.1002/chem.202102578
17. [17]
  X. Huang, L. Qian, Y. Zhou, et al., J. Mater. Chem. C 6 (2018) 5075–5096. doi: 10.1039/C8TC00043C
18. [18]
  S. Nagai, M. Yamashita, T. Tachikawa, et al., J. Mater. Chem. C 7 (2019) 4988–4998. doi: 10.1039/C9TC00157C
19. [19]
  C. Wang, Z. Li, Mater. Chem. Front. 1 (2017) 2174–2194. doi: 10.1039/C7QM00201G
20. [20]
  B. Fang, M. Chu, Z. Wu, et al., J. Mater. Chem. C 7 (2019) 4434–4440. doi: 10.1039/C9TC00156E
21. [21]
  F. Hu, W. Yang, L. Li, et al., Chem. Eng. J. 464 (2023) 142678. doi: 10.1016/j.cej.2023.142678
22. [22]
  Z. Wang, M. Wang, J. Peng, et al., J. Phys. Chem. C 123 (2019) 27742–27751. doi: 10.1021/acs.jpcc.9b06912
23. [23]
  X.Y. Shen, Y.J. Wang, E. Zhao, et al., J. Phys. Chem. C 117 (2013) 7334–7347. doi: 10.1021/jp311360p
24. [24]
  R. Pashazadeh, G. Sych, S. Nasiri, et al., Chem. Eng. J. 401 (2020) 125962. doi: 10.1016/j.cej.2020.125962
25. [25]
  A. Li, N. Chu, J. Liu, et al., Mater. Chem. Front. 3 (2019) 2768–2774. doi: 10.1039/C9QM00529C
26. [26]
  H.X. Yu, J. Zhi, T. Shen, et al., J. Mater. Chem. C 7 (2019) 8888–8897. doi: 10.1039/C9TC01772K
27. [27]
  G. Wu, F. Li, B. Tang, et al., J. Am. Chem. Soc. 144 (2022) 14962–14975. doi: 10.1021/jacs.2c02434
28. [28]
  R. Wang, H. Deng, W. Cheng, et al., Dyes Pigments 235 (2025) 112578. doi: 10.1016/j.dyepig.2024.112578
29. [29]
  J.R. Wu, G. Wu, D. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202218142. doi: 10.1002/anie.202218142
30. [30]
  S.J. Barrow, S. Kasera, M.J. Rowland, et al., Chem. Rev. 115 (2015) 12320–12406. doi: 10.1021/acs.chemrev.5b00341
31. [31]
  J. Lagona, P. Mukhopadhyay, S. Chakrabarti, et al., Angew. Chem. Int. Ed. 44 (2005) 4844–4870. doi: 10.1002/anie.200460675
32. [32]
  X. Yang, F. Liu, Z. Zhao, et al., Chin. Chem. Lett. 29 (2018) 1560–1566. doi: 10.1016/j.cclet.2018.01.032
33. [33]
  Y. Jiao, K. Liu, G. Wang, et al., Chem. Sci. 6 (2015) 3975–3980. doi: 10.1039/C5SC01167A
34. [34]
  F. Biedermann, E. Elmalem, I. Ghosh, et al., Angew. Chem. Int. Ed. 51 (2012) 7739–7743. doi: 10.1002/anie.201202385
35. [35]
  H. Nie, Z. Wei, X.L. Ni, et al., Chem. Rev. 122 (2022) 9032–9077. doi: 10.1021/acs.chemrev.1c01050
36. [36]
  R.N. Dsouza, U. Pischel, W.M. Nau, Chem. Rev. 111 (2011) 7941–7980. doi: 10.1021/cr200213s
37. [37]
  L. Mao, S. Li, X. Zhang, et al., Chin. Chem. Lett. 35 (2024) 109363–109373. doi: 10.1016/j.cclet.2023.109363
38. [38]
  X.K. Ma, Y. Liu, Acc. Chem. Res. 54 (2021) 3403–3414. doi: 10.1021/acs.accounts.1c00336
39. [39]
  G. Wu, Y.W. Yang, Cell Rep. Phys. Sci. 5 (2024) 101873–101886. doi: 10.1016/j.xcrp.2024.101873
40. [40]
  C. Yin, Z.A. Yan, X. Ma, Chem. Commun. 59 (2023) 13421–13433. doi: 10.1039/D3CC04051H
41. [41]
  D. Sun, Y. Wu, X. Han, et al., Nat. Commun. 14 (2023) 4190. doi: 10.1038/s41467-023-39956-7
42. [42]
  S. Kuang, Z. Hu, H. Zhang, et al., Chem. Commun. 54 (2018) 2169–2172. doi: 10.1039/C8CC00593A
43. [43]
  M. Megyesi, L. Biczók, I. Jablonkai, J. Phys. Chem. C 112 (2008) 3410–3416.
44. [44]
  Y. Gu, Z. Zhao, H. Su, et al., Chem. Sci. 9 (2018) 6497–6502. doi: 10.1039/C8SC01635F
45. [45]
  D. Sun, Y. Wu, X. Han, et al., Chem. Eur. J. 27 (2021) 16153–16160. doi: 10.1002/chem.202102731
46. [46]
  G. Wu, Y.J. Bae, M. Olesińska, et al., Chem. Sci. 11 (2020) 812–825. doi: 10.1039/C9SC04587B
47. [47]
  J. Yang, X. Hu, M. Fan, et al., Org. Chem. Front. 10 (2023) 422–429. doi: 10.1039/D2QO01831D
48. [48]
  X.H. Jin, C. Chen, C.X. Ren, et al., Chem. Commun. 50 (2014) 15878–15881. doi: 10.1039/C4CC07063A
49. [49]
  Y. Liu, Q. Zeng, B. Zou, et al., Angew. Chem. Int. Ed. 57 (2018) 15670–15674. doi: 10.1002/anie.201810149
50. [50]
  J. Liu, Y. Zhang, K. Zhang, et al., Org. Electron. 71 (2019) 212–219. doi: 10.1016/j.orgel.2019.05.028
51. [51]
  Y. Guo, A. Wu, Q. Zhang, et al., Chem. Eng. J. 497 (2024) 154721. doi: 10.1016/j.cej.2024.154721
1. [1]
  Yarui Li , Huangjie Lu , Yingzhe Du , Jie Qiu , Peng Lin , Jian Lin . Highly efficient separation of high-valent actinide ions from lanthanides via fractional crystallization. Chinese Journal of Structural Chemistry, 2025, 44(4): 100562-100562. doi: 10.1016/j.cjsc.2025.100562
2. [2]
  Min Huang , Ru Cheng , Shuai Wen , Liangtong Li , Jie Gao , Xiaohui Zhao , Chunmei Li , Hongyan Zou , Jian Wang . Ultrasensitive detection of microRNA-21 in human serum based on the confinement effect enhanced chemical etching of gold nanorods. Chinese Chemical Letters, 2024, 35(9): 109379-. doi: 10.1016/j.cclet.2023.109379
3. [3]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
4. [4]
  Fei Li , Yibin Sun , Bao Li , Siyuan Xu , Shuangyu Wu , Lixin Wu , Guanglu Wu . Portal-directed assembly of 2D cucurbituril-polyoxometalate hybrids toward synergistic photothermal catalysis. Chinese Chemical Letters, 2026, 37(8): 112034-. doi: 10.1016/j.cclet.2025.112034
5. [5]
  Saisai Yuan , Yiming Chen , Xijuan Wang , Degui Zhao , Tengyang Gao , Caiyun Wei , Chuanxiang Chen , Yang Yang , Wenjing Hong . Decouple the intermolecular interaction by encapsulating an insulating sheath. Chinese Chemical Letters, 2025, 36(6): 110816-. doi: 10.1016/j.cclet.2025.110816
6. [6]
  Da Yue , Tanglue Feng , Zhicheng Zhu , Mingcheng Zhang , Liyuan Chen , Xiao Han , Haizhu Sun , Bai Yang . Carbonized polymer dots confined active Ru-O sites for boosting electrocatalytic oxygen evolution. Chinese Chemical Letters, 2025, 36(11): 111393-. doi: 10.1016/j.cclet.2025.111393
7. [7]
  Jaeheon Lee , Jung Hyeun Kim . Effect of thermal annealing on cold crystallization ability of thermoset polyurethane elastomer synthesized from fully bio-derived polyol. Chinese Journal of Structural Chemistry, 2025, 44(5): 100568-100568. doi: 10.1016/j.cjsc.2025.100568
8. [8]
  Lanjun Cheng , Xinyuan Wang , Jie An , Xiang Wu , Chengfeng Zhu , Yanming Fu , Yougui Li . Improvement of the Resolution Experiment of Racemic Tartaric Acid. University Chemistry, 2025, 40(7): 277-285. doi: 10.12461/PKU.DXHX202408010
9. [9]
  Xiuqiong Zeng , Jiqing Cai , Chen Chen , Yanping Ren , Wan Li , Yongxian Fan , Faqiong Zhao , Wenwei Zhang , Mei Shi , Min Hu , Kai Hu , Xiuyun Wang , Weihong Li , Yong Fan , Xiaohang Qiu , Juanjuan Song , Dongcheng Liu , Jianrong Zhang , Shuyong Zhang . Suggestions on Dissolution, Crystallization and Crystal Cultivation. University Chemistry, 2026, 41(3): 191-199. doi: 10.12461/PKU.DXHX202507045
10. [10]
  Zhimin Sun , Shuo Guo , Jia-Qi Zhao , Ze-Qi Chen , Zhao-Xian Li , Chunju Li , He-Lue Sun . Switchable supramolecular chirality of phenylalanine-modified viologen within cucurbit[8]uril confinement. Chinese Chemical Letters, 2026, 37(7): 111823-. doi: 10.1016/j.cclet.2025.111823
11. [11]
  Xingxing Jiang , Yuxin Zhao , Yan Kong , Jianju Sun , Shangzhao Feng , Xin Lu , Qi Hu , Hengpan Yang , Chuanxin He . Support effect and confinement effect of porous carbon loaded tin dioxide nanoparticles in high-performance CO₂ electroreduction towards formate. Chinese Chemical Letters, 2025, 36(1): 109555-. doi: 10.1016/j.cclet.2024.109555
12. [12]
  Pei-Pei Liu , Jia-Bin Xing , Yue-Yang Liu , Ke Feng , Hui Wang , Dan-Wei Zhang , Wei Zhou , Gang Zhao , Jiaheng Zhang , Zhan-Ting Li . Sulfonatoproxylated cucurbit[7]urils as highly water-soluble and biocompatible excipients for solubilizing poorly soluble drugs and improving the bioavailability of indomethacin. Chinese Chemical Letters, 2025, 36(9): 110831-. doi: 10.1016/j.cclet.2025.110831
13. [13]
  Jun Lu , Jinrui Yan , Yaohao Guo , Junjie Qiu , Shuangliang Zhao , Bo Bao . Controlling solid form and crystal habit of triphenylmethanol by antisolvent crystallization in a microfluidic device. Chinese Chemical Letters, 2024, 35(4): 108876-. doi: 10.1016/j.cclet.2023.108876
14. [14]
  Xianchen Hu , Junli Yang , Fang Gao , Zhiyong Zhao , Simin Liu . Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host. Chinese Chemical Letters, 2025, 36(3): 109967-. doi: 10.1016/j.cclet.2024.109967
15. [15]
  Xia-Lin Dai , Yu-Hang Yao , Jian-Feng Zhen , Wei Gao , Jia-Mei Chen , Tong-Bu Lu . Reaction crystallization method based on deep eutectic solvents: A novel, green and efficient cocrystal synthesis approach. Chinese Chemical Letters, 2025, 36(11): 110413-. doi: 10.1016/j.cclet.2024.110413
16. [16]
  Shuang Li , Penghui Yuan , Xinyi Zhang , Meiru Liu , Dezhi Yang , Linglei Kong , Li Zhang , Yang Lu , Guanhua Du . Revolutionizing sepsis therapy: Machine learning-driven co-crystallization reveals emodin's therapeutic potential. Chinese Chemical Letters, 2026, 37(2): 111289-. doi: 10.1016/j.cclet.2025.111289
17. [17]
  Hao-Nan Qin , Hao Xie , Jia-Wang Yuan , Ren-Wu Huang , Zhao-Yang Wang , Shuang-Quan Zang . Crystallization-induced emission enhancement of copper iodide cluster for efficient X-ray scintillation and dynamic imaging. Chinese Chemical Letters, 2026, 37(9): 111529-. doi: 10.1016/j.cclet.2025.111529
18. [18]
  Lijun Mao , Shuo Li , Xin Zhang , Zhan-Ting Li , Da Ma . Cucurbit[n]uril-based nanostructure construction and modification. Chinese Chemical Letters, 2024, 35(8): 109363-. doi: 10.1016/j.cclet.2023.109363
19. [19]
  Heng Qiu , Wang Xie , Mingxia Ye , Conghao Shi , Juli Jiang , Zhouyu Wang , Wim Dehaen , Leyong Wang . Reaction-driven crystallization: Gram-scale synthesis of chiral macrocycles bearing Tröger's base with self-sorting. Chinese Chemical Letters, 2026, 37(7): 111966-. doi: 10.1016/j.cclet.2025.111966
20. [20]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(7)
HTML views(0)

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