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.
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http://dx.doi.org/10.1021/acs.orglett.6b02655 | DOI Listing |
Org Lett
November 2016
Department of Chemistry, University of Miami, Coral Gables, Florida 33124, United States.
Org Lett
March 2015
Department of Chemistry, University of Miami, Coral Gables, Florida 33124, United States.
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