Amphiphilic homopolymer as a reaction medium in water: Product selectivity within polymeric nanopockets

Selvanathan Arumugam, Dharma Rao Vutukuri, S. Thayumanavan, V. Ramamurthy

Research output: Contribution to journalArticle

71 Scopus citations

Abstract

A styrene-based water-soluble polymer has been explored for its use as a host for lipophilic substrates in aqueous medium. Unimolecular reactions, namely, photo-Fries rearrangement of naphthyl esters, α-cleavage reaction of 1-phenyl-3-p-tolyl-propan-2-one, and Norrish type I and type II reactions of benzoin alkyl ethers were examined. We find that the hydrophobic domains generated by the polymer not only restrict the mobility of the radicals but also modestly incarcerate the substrate, intermediates, and products during the time scale of the reactions. Comparative studies of the same photoreactions in micelles formed from small molecule surfactants and an amphiphilic diblock copolymer demonstrate that the styrene-based water-soluble polymer aggregates in aqueous medium offer better selectivity.

Original languageEnglish (US)
Pages (from-to)13200-13206
Number of pages7
JournalJournal of the American Chemical Society
Volume127
Issue number38
DOIs
StatePublished - Sep 28 2005

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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