Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation

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

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

By merging well-established concepts of supramolecular chemistry, protecting group strategy, and photochemistry, we have solubilized in water hydrophobic organic molecules consisting of a photoactive protecting group and masked carboxylic acids, released the desired acid, and confined a reactive carbocation intermediate within a capsule. Confinement of the photogenerated carbocation brought out the latent radical-like behavior. This observation is consistent with the recent theoretical prediction of the 7-(diethylamino)coumarinyl-4-methyl carbocation having a triplet diradical ground-state electronic contribution.

Original languageEnglish (US)
Pages (from-to)3588-3591
Number of pages4
JournalOrganic Letters
Volume19
Issue number13
DOIs
StatePublished - Jul 7 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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