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

ABSTRACT: 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 (?-, ?-, and ?-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.

SUBMITTER: Saleh N 

PROVIDER: S-EPMC7464550 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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

Saleh Na'il N   Bufaroosha Muna S MS   Moussa Ziad Z   Bojesomo Rukayat R   Al-Amodi Hebah H   Al-Ahdal Asia A  

Molecules (Basel, Switzerland) 20200814 16

<i>Cis</i>- or <i>Z</i>-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the <i>E</i>-form is inactive. Herein, we describe the encapsulation of <i>E</i>-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 <i>E</i>-CA and its methyl este  ...[more]

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