Photorelease of incarcerated caged acids from hydrophobic coumaryl esters into aqueous solution

Kamatham, Nareshbabu; Mendes, Débora C.; Silva, José P. da; Givens, Richard S.; Ramamurthy, V.

http://hdl.handle.net/10400.1/9214

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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.