刚性二苯代乙烯光响应动态超分子组装与调控

doi:10.6023/cjoc202312026

摘要/Abstract

刺激响应系统近些年因被广泛应用于材料科学和生命科学领域而备受关注. 动态超分子组装是通过引入刺激响应基团在不同的刺激因子影响下改变其功能团的结构进而改变超分子的组装模式而实现. 刚性二苯代乙烯作为一种常见的分子光开关, 在不同波长的光照射下发生顺反异构, 其空间构型发生较大改变, 并具有较好的光致异构特性, 已被广泛应用于可控催化、药物递送、分子机器及可调相转化等方面. 概述了刚性二苯代乙烯衍生物常见的一些合成方法和近些年在光开关离子受体、光驱动主客体组装、光响应氢键组装、光诱导金属键组装和光控亲疏水组装等光响应动态超分子组装方面的研究和应用.

关键词: 刚性二苯代乙烯, 光驱动, 离子受体, 超分子自组装

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

引用此文

曹巧红, 肖咏梅, 刘国星. 刚性二苯代乙烯光响应动态超分子组装与调控[J]. 有机化学, 2024, 44(7): 2124-2135.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 19

图式1. 刚性二苯代乙烯光致异构反应机理

Scheme 1. Mechanism of stiff-stilbene photoisomerization

图式2. 对称刚性二苯代乙烯的合成

Scheme 2. Synthesis of symmetrically stiff-stilbene

图式3. 不对称刚性二苯代乙烯的合成

Scheme 3. Synthesis of asymmetric stiff-stilbene

图式4. 刚性二苯代乙烯人工受体对磷酸根离子光/热响应络合示意图

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

图式5. 刚性二苯代乙烯人工受体对磷酸根离子/醋酸根离子光响应络合示意图(顺式结构效果较好)

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

图式6. 刚性二苯代乙烯人工受体对磷酸根离子/醋酸根离子光响应络合示意图(反式结构效果较好)

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

图式7. 杯吡咯修饰的刚性二苯代乙烯对氯离子光控络合示意图

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

图式8. 甘脲功能化的刚性二苯代乙烯对氯离子光控络合示意图

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

图1. 光控钾离子运输示意图

Figure 1. Schematic diagram of photocontrolled potassium ion transport

图2. 基于刚性二苯代乙烯/柱芳烃自锁轮烷分子机器

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

图3. 基于刚性二苯代乙烯/柱芳烃的光响应寡聚物-聚合物转换

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

图式9. 刚性二苯代乙烯冠醚大环对不同手性客体的光控选择性络合

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

图式10. 光驱动刚性二苯代乙烯/冠醚准[2]轮烷

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

图式11. 基于刚性二苯代乙烯/杯芳烃的超分子组装

图式12. 基于刚性二苯代乙烯/葫芦脲的超分子组装

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

图4. 刚性二苯代乙烯甘脲氢键自组装及光控相转变

图5. 酰胺刚性二苯代乙烯氢键自组装及光调控软材料机械性能

图式13. 基于刚性二苯代乙烯衍生物金属配位超分子组装

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

图6. 基于刚性二苯代乙烯衍生物亲疏水超分子组装

参考文献 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.