Photoresponsive Dynamic Supramolecular Assembly and Regulation of Stiff-Stilbenes

doi:10.6023/cjoc202312026

Abstract

Stimulus-response systems have attracted extensive attention in recent years due to their widespread applications in material science and biological science. Dynamic supramolecular assembly is achieved by introducing stimulus response groups to alter the structure of functional groups and then change supramolecular assembling patterns under the influence of different stimulated factors. As a common molecular photoswitch, stiff-stilbenes have been widely used in controlled catalysis, drug delivery, molecular machinery, tunable phase conversion and so on. Stiff-stilbenes occur Z-E isomerization upon irradiation at diverse light, accompanied by the great alteration of their geometry configuration, and possess good photoisomerization characteristics. Here, some common synthesis methods and photoisomerization mechanism of stiff-stilbene derivatives and their recent research and applications in the fields of photo-switchable ion receptor, light-driven host-guest assembly, photo-responsive hydrogen bond assembly, photoinduced metal bond assembly and photocontrolled hydrophilic and hydrophobic assembly are reviewed.

Key words: stiff-stilbene, photo-driven, ion receptor, supramolecular self-assembly

Cite this article

Qianhong Cao, Yongmei Xiao, Guoxing Liu. Photoresponsive Dynamic Supramolecular Assembly and Regulation of Stiff-Stilbenes[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2124-2135.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 19

Scheme 1. Mechanism of stiff-stilbene photoisomerization

Scheme 2. Synthesis of symmetrically stiff-stilbene

Scheme 3. Synthesis of asymmetric stiff-stilbene

Scheme 4. Schematic diagram of photo/thermal-responsive complexation of stiff-stilbene artificial receptors to phosphate anion

Scheme 5. Schematic diagram of photoresponsive complexation of stiff-stilbene artificial receptors to phosphate anions/acetate anions (cis-structure has a better effect)

Scheme 6. Schematic diagram of photoresponsive complexation of stiff-stilbene artificial receptors to phosphate anions/acetate anions (trans-structure has a better effect)

Scheme 7. Schematic diagram of photo-controlled complexation chloride ions by calypyrrole-modified stiff-stilbene Reprinted with permission from Ref. [52]. Copyright 2021 Royal Society of Chemistry

Scheme 8. Schematic diagram of photocontrolled complexation of chloride ions by bi-urea-functionalized stiff-stilbene

Figure 1. Schematic diagram of photocontrolled potassium ion transport

Figure 2. Self-locking rotaxane molecular machine based on stiff-stilbene/pillararene

Figure 3. Photoresponsive oligo-polymer conversion based on stiff-stilbene/pillararene

Scheme 9. Photocontrolled selective complexation of different chiral guests by stiff-stilbene crown ether macrocyclic host

Scheme 10. Photo-driven pseudo[2]rotaxane based on stiff-stilbene/crown ether

Scheme 12. Supramolecular assembly based on stiff-stilbene/ cucurbituril

Scheme 13. Supramolecular assembly based on metal coordination interaction of stiff-stilbene derivatives

References 77

[1]	Chen, M.; Zhong, M.; Johnson, J. A. Chem. Rev. 2016, 116, 10167. doi: 10.1021/acs.chemrev.5b00671 pmid: 26978484
[2]	Li, E.; Jie, K.; Liu, M.; Sheng, X.; Zhua, W.; Huang, F. Chem. Soc. Rev. 2020, 49, 1517.
[3]	Liu, G.; Xu, X.; Dai, X.; Jiang, C.; Zhou, Y.; Lu, L.; Liu, Y. Mater. Horiz. 2021, 8, 2494.
[4]	Liu, Y.; Ma, L.; Wang, Q.; Ma, X. Acta Chim. Sinica 2023, 81, 445. (in Chinese)
	(刘懿玮, 马良伟, 王巧纯, 马骧, 化学学报, 2023, 81, 445.) doi: 10.6023/A23030077
[5]	Wu, B.; Wang, C.; Li, B.; Wang, C. Acta Chim. Sinica 2022, 80, 101. (in Chinese)
	(吴波, 王冲, 李宝林, 王春儒, 化学学报, 2022, 80, 101.) doi: 10.6023/A21120564
[6]	Feringa, B. L.; Delden, R. A. V.; Koumura, N.; Geertsema, E. M. Chem. Rev. 2000, 100, 1789. pmid: 11777421
[7]	Volarić, J.; Szymanski, W.; Simeth, N. A.; Feringa, B. L. Chem. Soc. Rev. 2021, 50, 12377. doi: 10.1039/d0cs00547a pmid: 34590636
[8]	Imato, K.; Ishii, A.; Kaneda, N.; Hidaka, T.; Sasaki, A.; Imae, I.; Ooyama, Y. JACS Au 2023, 3, 2458.
[9]	Qu, D.; Wang, Q.; Zhang, Q.; Ma, X.; Tian, H. Chem. Rev. 2015, 115, 7543.
[10]	Wang, L.; Li, Q. Chem. Soc. Rev. 2018, 47, 1044.
[11]	Li, Z.; Zeng, X.; Gao, C.; Song, J.; He, F.; He, T.; Guo, H.; Yin, J. Coord. Chem. Rev. 2023, 497, 215451.
[12]	Liu, L.; Hao, T.; Wu, W.; Yang, C. Chin. J. Org. Chem. 2023, 43, 2189. (in Chinese)
	(刘铃, 浩涛涛, 伍晚花, 杨成, 有机化学, 2023, 43, 2189.) doi: 10.6023/cjoc202210020
[13]	Wang, J.; Feringa, B. L. Science 2011, 331, 1429.
[14]	Dorel, R.; Feringa, B. L. Chem. Commun. 2019, 55, 6477.
[15]	Kistemaker, J. C. M.; Lubbe, A. S.; Feringa, B. L. Mater. Chem. Front. 2021, 5, 2900.
[16]	Costil, R.; Holzheimer, M.; Crespi, S.; Simeth, N. A.; Feringa, B. L. Chem. Rev. 2021, 121, 13213.
[17]	Liu, G.; Leng, J.; Zhou, Q.; Deng, Z.; Shi, L.; Fan, C.; Xu, X.; Song, M.-P. Dyes Pigm. 2022, 203, 110361.
[18]	Xu, J.; Chen, Y.; Wu, D.; Wu, L.; Tung, C.; Yang, Q. Angew. Chem., Int. Ed. 2013, 52, 9738.
[19]	Liu, G.; Li, Y.; Tian, C.; Xiao, Y.; Liu, L.; Cao, Z.; Jiang, S.; Zheng, X.; Niu, C.; Ren, Y.-L.; Yang, L.; Zheng, X.; Chen, Y. Chin. Chem. Lett. 2023, DOI: 10.1016/j.cclet.2023.109403.
[20]	Xu, J.; Chen, Y.; Wu, L.; Tung, C.; Yang, Q. Org. Lett. 2014, 16, 684.
[21]	Liu, G.; Tian, C.; Fan, X.; Dang, Y.; Qin, J.; Liu, L.; Cao, Z.; Jiang, S. Org. Lett. 2023, 25, 8761.
[22]	Geertsema, E. M.; Koumura, N.; Wiel, M. K. J.; Meetsma, A.; Feringa, B. L. Chem. Commun. 2002, 2962.
[23]	Boursalian, G. B.; Nijboer, E. R.; Dorel, R.; Pfeifer, L.; Markovitch, O.; Blokhuis, A.; Feringa, B. L. J. Am. Chem. Soc. 2020, 142, 16868. doi: 10.1021/jacs.0c08249 pmid: 32905701
[24]	Hao, T.; Yang, Y.; Liang, W.; Fan, C.; Wang, X.; Wu, W.; Chen.; Fu, H.; Chen, H.; Yang, C. Chem. Sci. 2021, 12, 2614.
[25]	Villarón, D.; Wezenberg, S. J. Angew. Chem., Int. Ed. 2020, 59, 13192. doi: 10.1002/anie.202001031 pmid: 32222016
[26]	Sheng, J.; Pooler, D. R. S.; Feringa, B. L. Chem. Soc. Rev. 2023, 52, 5875.
[27]	McMurry, J. E. Chem. Rev. 1989, 89, 1513.
[28]	Lemmen, P.; Lenoir, D. Chem. Ber. 1984, 117, 2300.
[29]	Kucharski, T. J.; Huang, Z.; Tian, Y.; Rubin, N. C.; Concepcion, C. D.; Boulatov, R. Angew. Chem., Int. Ed. 2009, 48, 7040. doi: 10.1002/anie.200901511 pmid: 19533691
[30]	Akbulatov, S.; Tian, Y. C.; Boulatov, R. J. Am. Chem. Soc. 2012, 134, 7620. doi: 10.1021/ja301928d pmid: 22540320
[31]	Zhu, H.; Shangguan, L.; Xia, D.; Mondal, J. H.; Shi, B. Nanoscale 2017, 9, 8913.
[32]	Huang, Z.; Yang, Q.; Khvostichenko, D.; Kucharski, T. J.; Chen, J.; Boulatov, R. J. Am. Chem. Soc. 2009, 131, 1407. doi: 10.1021/ja807113m pmid: 19125573
[33]	Villarón, D.; Duindam, N.; Wezenberg, S. J. Chem.-Eur. J. 2021, 27, 17346. doi: 10.1002/chem.202103052 pmid: 34605565
[34]	Wu, Y.; Huang, K.; Chen, S.; Chen, Y.; Tung, C.; Wu, L. Sci. China: Chem. 2019, 62, 1194.
[35]	Jong, J. D.; Feringa, B. L.; Wezenberg, S. J. ChemPhysChem 2019, 20, 3306.
[36]	Hume, J. R.; Duan, D. Y.; Collier, M. L.; Yamazaki, J.; Horowitz, B. Physiol. Rev. 2000, 80, 31. pmid: 10617765
[37]	Kaplan, R. S. J. Membr. Biol. 2001, 179, 165.
[38]	Angeli, A. D.; Thomine, S.; Frachisse, J. M.; Ephritikhine, G.; Gambale, F.; Barbier-Brygoo, H. FEBS Lett. 2007, 581, 2367.
[39]	Ashcroft, F. M. Ion Channels and Disease: Channelopathies, Academic Press, 2000, p. 481.
[40]	Hein, R.; Beer, P. D.; Davis, J. J. Chem. Rev. 2020, 120, 1888.
[41]	Jong, J. D.; Bos, J. E.; Wezenberg, S. J. Chem. Rev. 2023, 123, 8530.
[42]	Park, C. H.; Simmons, H. E. J. Am. Chem. Soc. 1968, 90, 2431.
[43]	Nishizawa, S.; Bühlmann, P.; Iwao, M.; Umezawa, Y. Tetrahedron Lett. 1995, 36, 6483.
[44]	Snellink-Ruël, B. H. M.; Antonisse, M. M. G.; Engbersen, J. F. J.; Timmerman, P.; Reinhoudt, D. N. Eur. J. Org. Chem. 2000, 2000, 165.
[45]	Brooks, S. J.; Gale, P. A.; Light, M. E. Chem. Commun. 2005, 4696.
[46]	Brooks, S. J.; Edwards, P. R.; Gale, P. A.; Light, M. E. New. J. Chem. 2006, 30, 65.
[47]	Wezenberg, S. J.; Vlatković, M.; Kistemaker, J. C. M.; Feringa, B. L. J. Am. Chem. Soc. 2014, 136, 16784. doi: 10.1021/ja510700j pmid: 25402836
[48]	Vlatković, M.; Feringa, B. L.; Wezenberg, S. J. Angew. Chem., Int. Ed. 2016, 55, 1001. doi: 10.1002/anie.201509479 pmid: 26636270
[49]	Sheng, J.; Crespi, S.; Feringa, B. L.; Wezenberg, S. J. Org. Chem. Front. 2020, 7, 3874.
[50]	Wezenberg, S. J.; Feringa, B. L. Org. Lett. 2017, 19, 324. doi: 10.1021/acs.orglett.6b03423 pmid: 28074657
[51]	Leng, J.; Liu, G.; Cui, T.; Mao, S.; Dong, P.; Liu, W.; Hao, X.; Song, M. Dyes Pigm. 2021, 184, 108838.
[52]	Villarón, D.; Siegler, M. A.; Wezenberg, S. J. Chem. Sci. 2021, 12, 3188. doi: 10.1039/d0sc06686a pmid: 34164086
[53]	Wezenberg, S. J.; Chen, L.; Bos, J. E.; Feringa, B. L.; Howe, E. N. W.; Wu, X.; Siegler, M. A.; Gale, P. A. J. Am. Chem. Soc. 2022, 144, 331.
[54]	Villarón, D.; Bos, J. E.; Kohl, F.; Mommer, S.; Jong, J. D.; Wezenberg, S. J. J. Org. Chem. 2023, 88, 11328.
[55]	Yang, H.; Yi, J.; Pang, S.; Ye, K.; Ye, Z.; Duan, Q.; Yan, Z.; Lian, C.; Yang, Y.; Zhu, L.; Qu, D.; Bao, C. Angew. Chem., Int. Ed. 2022, 61, e202204605.
[56]	Tian, X.; Zuo, M.; Niu, P.; Wang, K.; Hu, X. Chin. J. Org. Chem. 2020, 40, 1823. (in Chinese)
	(田雪琪, 左旻瓒, 牛蓬勃, 王开亚, 胡晓玉, 有机化学, 2020, 40, 1823.) doi: 10.6023/cjoc202003066
[57]	Bian, S.; Ye, J.-H.; Fan, Z.; Zhang, W.; Wang, L. Chin. J. Org. Chem. 2016, 36, 855. (in Chinese)
	(卞松, 叶家海, 樊政, 张文超, 王乐勇, 有机化学, 2016, 36, 855.) doi: 10.6023/cjoc201510030
[58]	Wang, Z.-K.; Xu, Z.-Y.; Li, J.-J.; Yu, S.-B.; Wang, H.; Guo, D.-S.; Zhang, D.-W.; Li, Z.-T. Chin. J. Org. Chem. 2022, 42, 2236. (in Chinese)
	(王泽坤, 徐子悦, 李娟娟, 余尚博, 王辉, 郭东升, 张丹维, 黎占亭, 有机化学, 2022, 42, 2236.) doi: 10.6023/cjoc202202038
[59]	Zhang, Y.; Liu, Y. Chin. J. Org. Chem. 2020, 40, 3802. (in Chinese)
	(张依, 刘育, 有机化学, 2020, 40, 3802.) doi: 10.6023/cjoc202004040
[60]	Chen, Y.; Liu, Y. Chin. J. Org. Chem. 2012, 32, 805. (in Chinese)
	(陈湧, 刘育, 有机化学, 2012, 32, 805.) doi: 10.6023/cjoc1201124
[61]	Ogoshi, T. K., S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[62]	Wang, Y.; Xu, J.; Chen, Y.; Niu, L.; Wu, L.; Tung, C.; Yang, Q. Chem. Commun. 2014, 50, 7001.
[63]	Wang, Y.; Tian, Y.; Chen, Y.; Niu, L.; Wu, L.; Tung, C.; Yang, Q.; Boulatov, R. Chem. Commun. 2018, 54, 7991.
[64]	Wang, Y.; Sun, C.; Niu, L.; Wu, L.; Tung, C.; Chen, Y.; Yang, Q. Polym. Chem. 2017, 8, 3596.
[65]	Liu, Y.; Zhang, Q.; Crespi, S.; Chen, S.; Zhang, X.; Xu, T.; Ma, C.; Zhou, S.; Shi, Z.; Tian, H.; Feringa, B. L.; Qu, D. Angew. Chem., Int. Ed. 2021, 60, 16129.
[66]	Jong, J. D.; Siegler, M.; Wezenberg, S. Angew. Chem., Int. Ed. 2023, e202316628.
[67]	Alene, D.; Arumugaperumal, R.; Shellaiah, M.; Sun, K. W.; Chung, W. S. Org. Lett. 2021, 23, 2772.
[68]	Yang, L.; Li, Y.; Zhang, H.; Tian, C.; Cao, Q.; Xiao, Y.; Yuan, L.; Liu, G. Chin. Chem. Lett. 2023, 34, 108108.
[69]	Xiao, T.; Zhou, L.; Wei, X.; Li, Z.; Sun, X. Chin. J. Org. Chem. 2020, 40, 944. (in Chinese)
	(肖唐鑫, 周玲, 魏小艳, 李正义, 孙小强, 有机化学, 2020, 40, 944.) doi: 10.6023/cjoc201911014
[70]	Wezenberg, S. J.; Croisetu, C. M.; Stuartab, M. C. A.; Feringa, B. L. Chem. Sci. 2016, 7, 4341. doi: 10.1039/c6sc00659k pmid: 30155080
[71]	Xu, F.; Pfeifer, L.; Crespi, S.; Leung, F. K.; Stuart, M. C. A.; Wezenberg, S. J.; Feringa, B. L. J. Am. Chem. Soc. 2021, 143, 5990.
[72]	Xu, F.; Crespi, S.; Pacella, G.; Fu, Y.; Stuart, M. C. A.; Zhang, Q.; Portale, G.; Feringa, B. L. J. Am. Chem. Soc. 2022, 144, 6019.
[73]	Shan, Y.; Zhang, Q.; Sheng, J.; Stuart, M. C. A.; Qu, D.; Feringa, B. L. Angew. Chem., Int. Ed. 2023, 62, e202310582.
[74]	Yan, X.; Xu, J.; Cook, T. R.; Stang, P. J. Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 8717.
[75]	Zhao, D.; Leeuwen, T. V.; Cheng, J.; Feringa, B. L. Nat. Chem. 2017, 9, 250.
[76]	Kwan, K. S. Y.; Lui, Y.; Kajitani, T.; Leung, F. K. Macromol. Rapid Commun. 2022, 43, 2200438.
[77]	Chau, A. K.; Cheung, L. H.; Leung, F. K. Dyes Pigm. 2022, 208, 110807.

刚性二苯代乙烯光响应动态超分子组装与调控