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

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

Research output: Contribution to journalArticle

15 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 languageEnglish (US)
Pages (from-to)1276-1279
Number of pages4
JournalOrganic Letters
Volume17
Issue number5
DOIs
StatePublished - Mar 6 2015

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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