Photorelease of Incarcerated Caged Acids from Hydrophobic Coumaryl Esters into Aqueous Solution

Nareshbabu Kamatham, Débora C. Mendes, José P. Da Silva, Richard S. Givens, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Photolysis of aqueous solutions of carboxylic acid esters of 7-(methoxycoumaryl)-4-methanol included within the capsule made up of two molecules of octaacid released the acids in water. The trigger 7-(methoxycoumaryl)-4-methyl chromophore remains within octaacid either as the alcohol or as an adduct with the host octaacid through a hydrogen abstraction process. The method established here offers a procedure to release hydrophobic acid molecules in water at will in a timely manner with light. In addition, the system offers an unanticipated opportunity to probe the mechanistic dichotomy of a diradicaloid intermediate expressing both radical and ionic behavior when generated by coumarylmethyl ester photolysis in a hydrophobic environment.

Original languageEnglish (US)
Pages (from-to)5480-5483
Number of pages4
JournalOrganic Letters
Volume18
Issue number21
DOIs
StatePublished - Nov 4 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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