4.2 Article

Synthesis of lipo-glycopolymer amphiphiles by nitroxide-mediated living free-radical polymerization

Journal

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume 40, Issue 20, Pages 3379-3391

Publisher

JOHN WILEY & SONS INC
DOI: 10.1002/pola.10428

Keywords

living radical; nitroxide; lipopolymers; glycopolymers; block copolymers; biomacromolecules; amphiphiles; bioengineering

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The nitroxide-mediated living free-radical polymerization of 1,2,5,6-di(isopropylidene)-D-glucose-2-propenoate was achieved in dimethylformamide at 105 degreesC with an alpha-hydrido alkoxyamine initiator functionalized with a lipophilic N,N-di(octadecyl)amine group, The kinetics of the polymerization were investigated, and the mechanism was shown to be a living process allowing, after hydrolysis, controlled molecular weight, low-polydispersity lipo-glycopolymers to be prepared. The amphiphilic character of the macromolecule could be altered by either the exchange of the alkoxyamine at the chain end with hydrogen or the preparation of copolymers with lipophilic monomers such as N,N-di(octadecyl)acrylamide. The surface and membrane-forming properties of these novel lipopolymers demonstrate their amphiphilic character. (C) 2002 Wiley Periodicals, Inc.

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