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 |
|---|---|
| Pages (from-to) | 13200-13206 |
| Number of pages | 7 |
| Journal | Journal of the American Chemical Society |
| Volume | 127 |
| Issue number | 38 |
| DOIs | |
| State | Published - Sep 28 2005 |
Fingerprint
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Amphiphilic homopolymer as a reaction medium in water : Product selectivity within polymeric nanopockets. / Arumugam, Selvanathan; Vutukuri, Dharma Rao; Thayumanavan, S.; Ramamurthy, Vaidhyanathan.
In: Journal of the American Chemical Society, Vol. 127, No. 38, 28.09.2005, p. 13200-13206.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Amphiphilic homopolymer as a reaction medium in water
T2 - Product selectivity within polymeric nanopockets
AU - Arumugam, Selvanathan
AU - Vutukuri, Dharma Rao
AU - Thayumanavan, S.
AU - Ramamurthy, Vaidhyanathan
PY - 2005/9/28
Y1 - 2005/9/28
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=25444433861&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=25444433861&partnerID=8YFLogxK
U2 - 10.1021/ja051107v
DO - 10.1021/ja051107v
M3 - Article
C2 - 16173747
AN - SCOPUS:25444433861
VL - 127
SP - 13200
EP - 13206
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 38
ER -