Encapsulation of cinnamic acid by cucurbit[7]uril for enhancing photoisomerization

Na'il Saleh, Muna S. Bufaroosha, Ziad Moussa, Rukayat Bojesomo, Hebah Al-Amodi, Asia Al-Ahdal

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

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 (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.

Original languageEnglish
Article number3702
JournalMolecules
Volume25
Issue number16
DOIs
Publication statusPublished - Aug 2020

Keywords

  • Cis-cinnamic acid
  • Cucurbituril
  • Light stimuli
  • Photoisomerization
  • Responsiveness

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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