Abstract
In summary, we presented a design strategy for a chiral, amphiphilic, and photoswitchable molecule, using cholesterol, sulfonate, and cyanostilbene. The molecule could self-assemble to the trans-isomer in aqueous solution, which is accompanied by strong CD signals. Both trans- and cis-isomers are thermally stable, and the high conversion photoswitching between the trans- and cis-isomers with good fatigue resistance and reversibility, can be achieved using different wavelengths of UV irradiation. Furthermore, the optical chirality-CD was also modulated by UV irradiation. According to the TEM images and dynamic light scattering data, the photoswitching process involves self-assembly/disassembly from approximately 150 nm spherical particles to 18 nm irregular particles. We proposed a rational strategy using light-driven self-assembly for a molecular photoswitch in which optical chirality can be modulated by light irradiation in aqueous media.
摘要
人工手性自组装一直是分子化学与材料化学的前沿挑战性课题. 但由于缺少合适的手性光响应结构单元, 构造具有光控、可逆、手性 专一性响应的分子体系具有很大的挑战性. 本工作通过合理的分子设 计: 以氰基二苯乙烯作为光致异构基团, 磺酸基作为亲水基团, 胆固醇 作为疏水手性基团, 构造了独特的光响应组装体系. 当氰基二苯乙烯处 于反式构型时, 在水相中组装形成规则的球状组装体且具有较强的手 性信号. 通过365 nm光照后, 反式构型转变为顺式构型, 球状组装体解 组装, 同时手性信号消失; 当采用254 nm光照后, 重新形成具有手性信 号的球状组装体. 核磁共振和吸收光谱结果表明光致异构转化率达到 90%, 并且具有良好的光致异构重复性(抗疲劳性)及热稳定性. 本研究 成功实现了水相介质中光控、手性专一性响应的可逆光调控, 在构建 双稳态光控手性开关方面表现出潜在的应用前景.
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Acknowledgements
This work was supported by the National Natural Science Foundation of China (21875143 and 21908146), the Innovation Research Foundation of Shenzhen (JCYJ20180507182229597), and the Natural Science Foundation of Guangdong Province (2016A030312002). Special thanks to the Instrumental Analysis of Shenzhen University (Lihu Campus).
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Wu Y and Yu ZQ conceived the research; Wu Y and Zeng X designed the experiments; Zeng X, Zou L, Liu X and Qi X performed the experiments; Zeng X, Wu Y and Yu ZQ analyzed the data; Wu Y and Zeng X wrote the original draft; Wu Y and Yu ZQ completed the manuscript.
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The authors declare that they have no conflict of interest.
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Experimental details and supporting data are available in the online version of the paper.
Xiaoxuan Zeng received her BSc degree from Huizhou University (2019). She is now an MSc student at the College of Chemistry and Environmental Engineering, Shenzhen University, under Prof. Zhen-Qiang Yu’s supervision. Her research topic is chiral luminescent materials.
Yue Wu received his BSc degree from Jiangnan University and PhD degree from East China University of Science and Technology in 2014. Then he worked for Wilmar-Arowana as a senior R&D engineer for four years. In 2019, he joined Shenzhen University. Currently, his research interests focus on chiral luminescence and photoswitch.
Zhen-Qiang Yu received his BSc and PhD degrees from the Department of Chemistry, Beijing Normal University in 1997 and the College of Chemistry, Peking University in 2007, respectively. He joined the College of Chemistry and Environmental Engineering, Shenzhen University in 2007, where he is currently an associate professor. His research interests are focused on the synthesis, structures, properties and applications of functional materials.
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Zeng, X., Wu, Y., Zou, L. et al. Light-driven self-assembly of cyanostilbene derivative with reversible chirality in aqueous media. Sci. China Mater. 65, 1413–1416 (2022). https://doi.org/10.1007/s40843-021-1897-x
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DOI: https://doi.org/10.1007/s40843-021-1897-x