Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger

Pradeepkumar Jagadesan; José P. Da Silva; Richard S. Givens; Vaidhyanathan Ramamurthy

doi:10.1021/acs.orglett.5b00252

Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger

Pradeepkumar Jagadesan, José P. Da Silva, Richard S. Givens, Vaidhyanathan Ramamurthy

Chemistry

Research output: Contribution to journal › Article

14 Scopus citations

Abstract

We report the clean, efficient photorelease of a series of carboxylic acids embedded in octa acid (OA) host and protected by a p-hydroxyphenacyl cage. A key role is played by the cage by providing hydrophobicity for entry into the OA enclosure and yet readily removable as a photoactivated protecting group for release from the host. The rapid photo-Favorskii rearrangement of the departing chromophore does not react with the host OA but diminishes hydrophobicity of the OA contents, leading to their facile release into the solvent.

Original language	English (US)
Pages (from-to)	1276-1279
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.5b00252
State	Published - Mar 6 2015

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ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

Cite this

Jagadesan, P., Da Silva, J. P., Givens, R. S., & Ramamurthy, V. (2015). Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger. Organic Letters, 17(5), 1276-1279. https://doi.org/10.1021/acs.orglett.5b00252

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10.1021/acs.orglett.5b00252