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

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

doi:10.1021/ja051107v

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

75 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 language	English (US)
Pages (from-to)	13200-13206
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	127
Issue number	38
DOIs	https://doi.org/10.1021/ja051107v
State	Published - Sep 28 2005

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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