Citation: Hui-Juan Wang, Heng-Yi Zhang, Wen-Wen Xing, Huang Wu, Yong-Liang Cui, Yu Liu. Photodimerization-induced transition of helixes to vesicles based on coumarin-12-crown-4[J]. Chinese Chemical Letters, ;2022, 33(8): 4033-4036. doi: 10.1016/j.cclet.2021.12.051 shu

Photodimerization-induced transition of helixes to vesicles based on coumarin-12-crown-4

Hui-Juan Wang ^a ,
Heng-Yi Zhang ^a ,
Wen-Wen Xing ^a ,
Huang Wu ^b ,
Yong-Liang Cui ^a ,
Yu Liu ^{a, *,}

a.
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
b.
Department of Chemistry, Northwestern University, Evanston, IL 60208, United States

yuliu@nankai.edu.cn

Received Date: 27 September 2021
Revised Date: 15 December 2021
Accepted Date: 22 December 2021
Available Online: 26 December 2021

Figures(5)

Rational construction of fine-tuning and precisely controllable topological nanostructures based on supramolecular self-assembly system remains a challenge. Herein, coumarin-12-crown-4 (1) as a building block was synthesized by one-pot method and showed reversible high stereo-selective photodimerization (anti-head-to-head dimer (anti-HH-1): syn-head-to-head dimer (syn-HH-1) = 10.8:1) and photocleavage. Helical nanobelts were formed by the self-assembly of 1 through asymmetrical H-bonds, which were in concordance with the crystal state superstructure. Upon irradiation with 365 nm light, these nanobelts transformed into nanoballs which were constructed by three building blocks. Further, we investigated the photoreaction of 1 and got two pure covalent dimers (anti-HH-1 and syn-HH-1). The anti-HH-1 self-assembled into hollow micro-vesicles. The transformation of superstructures based on photo-controlled multiple blocks shines a light to the research on the relationship between molecules and superstructures.
- Reversible photodimerization,
- Superstructures,
- Coumarin,
- Supramolecular self-assembly,
- Molecular stacking
1. [1]
  X. Dou, N. Mehwish, C. Zhao, et al., Acc. Chem. Rev.53 (2020) 852–862. doi: 10.1021/acs.accounts.0c00012
2. [2]
  X. Zhou, H. Zhao, S. Liu, et al., Chin. Chem. Lett. 32 (2021) 761–764. doi: 10.1016/j.cclet.2020.05.023
3. [3]
  P. Xing, Y. Zhao, Adv. Mater. 28 (2016) 7304–7339. doi: 10.1002/adma.201600906
4. [4]
  J.H. Jung, Y. Ono, K. Sakurai, M. Sano, S. Shinkai, J. Am. Chem. Soc. 122 (2000) 8648–8653;. doi: 10.1021/ja001623f
5. [5]
  L. Li, W. Tuo, Q. Zhu, et al., J. Am. Chem. Soc. 142 (2020) 20583–20587. doi: 10.1021/jacs.0c10901
6. [6]
  S. Yagai, Y. Kitamoto, S. Datta, B. Adhikari, Acc. Chem. Res. 52 (2019) 1325–1335. doi: 10.1021/acs.accounts.8b00660
7. [7]
  L. Zhang, Y.M. Zhang, G.X. Liu, Y. Liu, Chin. Chem. Lett. 30 (2019) 120–122. doi: 10.1016/j.cclet.2018.04.028
8. [8]
  P. Xing, Y. Li, Y. Wang, et al., Angew. Chem. Int. Ed. 57 (2018) 7774–7779. doi: 10.1002/anie.201802825
9. [9]
  G. Yu, M. Xue, Z. Zhang, et al., J. Am. Chem. Soc. 134 (2012) 13248–13251. doi: 10.1021/ja306399f
10. [10]
  T. Zhang, Y.H. Liu, B.W. Hu, et al., Chin. Chem. Lett. 30 (2019) 949–952. doi: 10.1016/j.cclet.2018.12.029
11. [11]
  G. Liu, J. Sheng, W.L. Teo, et al., J. Am. Chem. Soc. 140 (2018) 16275–16283. doi: 10.1021/jacs.8b10024
12. [12]
  H.L. Sun, Y. Chen, X. Han, Y. Liu, Angew. Chem. Int. Ed. 56 (2017) 7062–7065. doi: 10.1002/anie.201612629
13. [13]
  S. Yagai, M. Yamauchi, A. Kobayashi, et al., J. Am. Chem. Soc. 134 (2012) 18205–18208. doi: 10.1021/ja308519b
14. [14]
  M. Yamauchi, T. Ohba, T. Karatsu, S. Yagai, Nat. Commun. 6 (2015) 8936. doi: 10.1038/ncomms9936
15. [15]
  J. Zhang, Q. Zou, H. Tian, Adv. Mater. 25 (2013) 378–399. doi: 10.1002/adma.201201521
16. [16]
  H. He, M. Feng, Q. Chen, X. Zhang, H. Zhan, Angew. Chem. Int. Ed. 55 (2016) 936–940. doi: 10.1002/anie.201508355
17. [17]
  Y. Cao, Y. Chen, Z. Zhang, et al., Chin. Chem. Lett. 32 (2021) 349–352. doi: 10.1016/j.cclet.2020.03.058
18. [18]
  S.R. Trenor, A.R. Shultz, B.J. Love, E.T. Long, Chem. Soc. Rev. 104 (2004) 3059–3077. doi: 10.1021/cr030037c
19. [19]
  J.W. Chung, K. Lee, C. Neikirk, C.M. Nelson, Small 8 (2012) 1693–1700. doi: 10.1002/smll.201102263
20. [20]
  P.P. Jia, L. Xu, Y.X. Hu, et al., J. Am. Chem. Soc. 143 (2021) 399–408. doi: 10.1021/jacs.0c11370
21. [21]
  H. Yan, F. Huo, Y. Yue, J. Chao, C. Yin, J. Am. Chem. Soc. 143 (2021) 318–325. doi: 10.1021/jacs.0c10840
22. [22]
  J. Motoyanagi, T. Fukushima, N. Ishii, T. Aida, J. Am. Chem. Soc. 128 (2006) 4220–4221. doi: 10.1021/ja060593z
23. [23]
  F. Wang, H. Qiu, C. Feng, Adv. Funct. Mater. 30 (2020) 2002936. doi: 10.1002/adfm.202002936
24. [24]
  S. Wang, M.C. Forster, K. Xue, et al., Angew. Chem. Int. Ed. 60 (2021) 9712–9718. doi: 10.1002/anie.202100153
25. [25]
  J.H. Jung, H. Kobayashi, M. Masuda, T. Shimizu, S. Shinkai, J. Am. Chem. Soc. 123 (2001) 8785–8789. doi: 10.1021/ja010508h
26. [26]
  H. Fenniri, B.L. Deng, A.E. Ribbe, et al., Proc. Natl. Acad. Sci. U. S. A. 99 (2002) 6487–6492. doi: 10.1073/pnas.032527099
27. [27]
  H. Fenniri, B.L. Deng, A.E. Ribbe, J. Am. Chem. Soc. 124 (2002) 11064–11072. doi: 10.1021/ja026164s
28. [28]
  J.H. Jung, Y. Ono, K. Sakurai, M. Sano, S. Shinkai, J. Am. Chem. Soc. 122 (2000) 8648–8653. doi: 10.1021/ja001623f
29. [29]
  J.H. Jung, H. Kobayashi, M. Masuda, T. Shimizu, S. Shinkai, J. Am. Chem. Soc. 123 (2001) 8785–8789.
30. [30]
  J.H. Jung, Y. Ono, S. Shinkai, Langmuir 16 (2000) 1643–1649.
31. [31]
  H. Engelkamp, S. Middelbeek, R.J.M. Nolte, Science 284 (1999) 785–788.
32. [32]
  H.J. Wang, H.Y. Zhang, H. Wu, et al., Chem. Commun. 55 (2019) 4499–4502. doi: 10.1039/c9cc01874c
33. [33]
  W. Zhang, Y.M. Zhang, S.H. Li, et al., Angew. Chem. Int. Ed. 55 (2016) 11452–11456;. doi: 10.1002/anie.201605420
34. [34]
  P. Wei, H. Wang, K. Jie, F. Huang. Chem. Commun. 53 (2017) 1688–1691. doi: 10.1039/C6CC10089A
35. [35]
  G.M.J. Schmidt, Pure Appl. Chem. 27 (1971) 647–678. doi: 10.1351/pac197127040647
36. [36]
  S.R. Trenor, A.R. Shultz, B.J. Love, T.E. Long, Chem. Rev. 104 (2004) 3059–3078.
37. [37]
  X. Yu, D. Scheller, O. Rademacher, T. Wolff, J. Org. Chem. 68 (2003) 7386–7399. doi: 10.1021/jo034627m
38. [38]
  J. Jiang, B. Qi, M. Lepage, Y. Zhao, Macromolecules 40 (2007) 790–792. doi: 10.1021/ma062493j
39. [39]
  N.K. Mal, M. Fujiwara, Y. Tanaka, Nature 421 (2003) 350–353.
40. [40]
  W. Ali, W. Gong, M. Hassan, et al., Chin. Chem. Lett. 32 (2021) 371–374.
41. [41]
  P.Y. Li, Y. Chen, Y. Liu, Chin. Chem. Lett. 30 (2019) 1190–1197.
1. [1]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
2. [2]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
3. [3]
  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
4. [4]
  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
5. [5]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
6. [6]
  Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306
7. [7]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
8. [8]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
9. [9]
  Guoxing Liu , Yixin Li , Changming Tian , Yongmei Xiao , Lijie Liu , Zhanqi Cao , Song Jiang , Xin Zheng , Caoyuan Niu , Yun-Lai Ren , Liangru Yang , Xianfu Zheng , Yong Chen . Highly reversible photomodulated hydrosoluble stiff-stilbene supramolecular luminophor induced by cucurbituril. Chinese Chemical Letters, 2024, 35(8): 109403-. doi: 10.1016/j.cclet.2023.109403
10. [10]
  Jiao Li , Chenyang Zhang , Chuhan Wu , Yan Liu , Xuejian Zhang , Xiao Li , Yongtao Li , Jing Sun , Zhongmin Su . Defined organic-octamolybdate crystalline superstructures derived Mo₂C@C as efficient hydrogen evolution electrocatalysts. Chinese Chemical Letters, 2024, 35(6): 108782-. doi: 10.1016/j.cclet.2023.108782
11. [11]
  Bowen Li , Ting Wang , Ming Xu , Yuqi Wang , Zhaoxing Li , Mei Liu , Wenjing Zhang , Ming Feng . Structuring MoO₃-polyoxometalate hybrid superstructures to boost electrocatalytic hydrogen evolution reaction. Chinese Chemical Letters, 2025, 36(2): 110467-. doi: 10.1016/j.cclet.2024.110467
12. [12]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
13. [13]
  Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431
14. [14]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
15. [15]
  Zixi Zou , Jingyuan Wang , Yian Sun , Qian Wang , Da-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972
16. [16]
  Qinghong Pan , Huafang Zhang , Qiaoling Liu , Donghong Huang , Da-Peng Yang , Tianjia Jiang , Shuyang Sun , Xiangrong Chen . A self-powered cathodic molecular imprinting ultrasensitive photoelectrochemical tetracycline sensor via ZnO/C photoanode signal amplification. Chinese Chemical Letters, 2025, 36(1): 110169-. doi: 10.1016/j.cclet.2024.110169
17. [17]
  Fengyao Cui , Qiaona Zhang , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Reversible phosphorescence in pseudopolyrotaxane elastomer. Chinese Chemical Letters, 2024, 35(10): 110061-. doi: 10.1016/j.cclet.2024.110061
18. [18]
  Wenlong Li , Feishi Shan , Qingdong Bao , Qinghua Li , Hua Gao , Leyong Wang . Supramolecular assembly nanoparticle for trans-epithelial treatment of keratoconus. Chinese Chemical Letters, 2024, 35(10): 110060-. doi: 10.1016/j.cclet.2024.110060
19. [19]
  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
20. [20]
  Zhu Shu , Xin Lei , Yeye Ai , Ke Shao , Jianliang Shen , Zhegang Huang , Yongguang Li . ATP-induced supramolecular assembly based on chromophoric organic molecules and metal complexes. Chinese Chemical Letters, 2024, 35(11): 109585-. doi: 10.1016/j.cclet.2024.109585

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(326)
HTML views(31)

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