Encapsulation of Cinnamic Acid by Cucurbit[7]uril for Enhancing Photoisomerization

Molecules

Na’il Saleh¹  Ziad Moussa¹  Hebah Al-Amodi¹  MunaS. Bufaroosha¹  Asia Al-Ahdal¹  Rukayat Bojesomo¹ 

[1] Department of Chemistry, College of Science, United Arab Emirates University, P.O. Box 15551 Al Ain, UAE;

关键词: cis-cinnamic acid;    cucurbituril;    photoisomerization;    responsiveness;    light stimuli;   

DOI  :  10.3390/molecules25163702

来源: DOAJ

【 摘 要 】

Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Herein, we describe the encapsulation of E-CA by cucurbit[7]uril (CB7) and show that photoisomerization reactions can be more efficiently controlled in aqueous solutions by utilizing this supramolecular approach. Measurements of UV–visible absorption and proton NMR spectra at different pH values confirm that E-CA and its methyl ester, methyl-E-cinnamate (MC), form stronger 1:1 host–guest complexes with CB7 compared to cucurbit[8]uril (CB8) or three cyclodextrins (α-, β-, and γ-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-bound E isomers induces E to Z photoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light, Z to E conformational changes of the unbound Z isomers are observed and are accompanied by restoring the host–guest complex formation.

【 授权许可】

Unknown