Controlling the isomerization of photoresponsive molecules through a limiting tautomerization strategy

article Controlling the isomerization of photoresponsive molecules through a limiting tautomerization strategy published yes Yongli Duan author Haiquan Zhao author Guodong Xue author Fanxi Sun author Friedrich J Stricker author 7aca2cfc-46cf-11f0-abd3-8c96b5186745 Zhen Wang author Lijun Mao author Chao He author Javier Read de Alaniz author Yonghao Zheng author Dongsheng Wang author Controlling the multistage photoresponsivity remains a challenge, in part, due to the spontaneous tautomerization between isomers. Herein, we present a strategy to access three independent states (linear, cyclic keto, and cyclic enolate) of crown ether (CE)-substituted donor–acceptor Stenhouse adducts (DASAs) by limiting the tautomerization of the closed isomers. The linear–cyclic keto isomerization is reversibly triggered by treatment with metal ions (Na+ or K+) and CE, while the linear–cyclic enolate isomerization is induced by green light and heat. Density functional theory and molecular dynamics calculation results suggest that the steric effect and supramolecular interaction between the electron-donating and electron-withdrawing moieties play an important role in hindering the tautomerization between cyclic keto and cyclic enolate DASA-CE. The strategy to influence key steps in the photoswitching process inspires well-controlled multistage isomerization of photoresponsive molecules. American Chemical Society2022 eng The Journal of Physical Chemistry B 1520-6106 1520-5207 3547196910.1021/acs.jpcb.2c02005 126173347-3354 yes Duan, Y., Zhao, H., Xue, G., Sun, F., Stricker, F. J., Wang, Z., … Wang, D. (2022). Controlling the isomerization of photoresponsive molecules through a limiting tautomerization strategy. The Journal of Physical Chemistry B. American Chemical Society. <a href="https://doi.org/10.1021/acs.jpcb.2c02005">https://doi.org/10.1021/acs.jpcb.2c02005</a> Y. Duan, H. Zhao, G. Xue, F. Sun, F.J. Stricker, Z. Wang, L. Mao, C. He, J.R. de Alaniz, Y. Zheng, D. Wang, The Journal of Physical Chemistry B 126 (2022) 3347–3354. Duan Y, Zhao H, Xue G, et al. Controlling the isomerization of photoresponsive molecules through a limiting tautomerization strategy. The Journal of Physical Chemistry B. 2022;126(17):3347-3354. doi:<a href="https://doi.org/10.1021/acs.jpcb.2c02005">10.1021/acs.jpcb.2c02005</a> Duan, Yongli, et al. “Controlling the Isomerization of Photoresponsive Molecules through a Limiting Tautomerization Strategy.” The Journal of Physical Chemistry B, vol. 126, no. 17, American Chemical Society, 2022, pp. 3347–54, doi:<a href="https://doi.org/10.1021/acs.jpcb.2c02005">10.1021/acs.jpcb.2c02005</a>. Duan, Yongli, Haiquan Zhao, Guodong Xue, Fanxi Sun, Friedrich J Stricker, Zhen Wang, Lijun Mao, et al. “Controlling the Isomerization of Photoresponsive Molecules through a Limiting Tautomerization Strategy.” The Journal of Physical Chemistry B. American Chemical Society, 2022. <a href="https://doi.org/10.1021/acs.jpcb.2c02005">https://doi.org/10.1021/acs.jpcb.2c02005</a>. Y. Duan et al., “Controlling the isomerization of photoresponsive molecules through a limiting tautomerization strategy,” The Journal of Physical Chemistry B, vol. 126, no. 17. American Chemical Society, pp. 3347–3354, 2022. Duan Y, Zhao H, Xue G, Sun F, Stricker FJ, Wang Z, Mao L, He C, de Alaniz JR, Zheng Y, Wang D. 2022. Controlling the isomerization of photoresponsive molecules through a limiting tautomerization strategy. The Journal of Physical Chemistry B. 126(17), 3347–3354. 218092026-05-06T10:45:18Z2026-05-11T07:28:38Z