Free Radical Polymers with Tunable and Selective Bio- and Chemical Degradability

Jos Marie Johannes Paulusse, Roey J. Amir, Richard A. Evans, Craig J. Hawker

Research output: Contribution to journalArticleAcademic

44 Citations (Scopus)

Abstract

A versatile synthetic strategy has been developed which enables the facile incorporation of cleavable functional groups, i.e., esters, thioesters, and disulfides, into the carbon−carbon backbone of vinyl-based polymers. Through the synthesis of novel cyclic monomers, RAFT-mediated radical ring-opening copolymerizations with traditional vinyl monomers such as methyl methacrylate, N,N-dimethylaminoethyl methacrylate, and 2-hydroxyethyl methacrylate lead to the introduction of controlled degradability into these widely used vinyl copolymer systems. An additional benefit of this strategy is the inherent versatility available through the incorporation of cyclic monomers containing diverse functional groups such as esters, thioesters, disulfides, and silyl ether units that allow degradation under basic/acidic, reductive, or enzymatic conditions. By integrating multiple, orthogonal cyclic monomers into linear copolymer backbones, well-defined systems with programmable degradation profiles are obtained which allows for tunable, selective, and stepwise degradation of the vinyl polymer backbones.
Original languageEnglish
Pages (from-to)9805-9812
Number of pages8
JournalJournal of the American Chemical Society
Volume131
Issue number28
DOIs
Publication statusPublished - 2009

Fingerprint

Free radicals
Disulfides
Free Radicals
Polymers
Esters
Monomers
Methacrylates
Degradation
Ether
Functional groups
Copolymers
Copolymerization
Ethers
hydroxyethyl methacrylate
2-(dimethylamino)ethyl methacrylate

Keywords

  • IR-99618

Cite this

Paulusse, Jos Marie Johannes ; Amir, Roey J. ; Evans, Richard A. ; Hawker, Craig J. / Free Radical Polymers with Tunable and Selective Bio- and Chemical Degradability. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 28. pp. 9805-9812.
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Free Radical Polymers with Tunable and Selective Bio- and Chemical Degradability. / Paulusse, Jos Marie Johannes; Amir, Roey J.; Evans, Richard A.; Hawker, Craig J.

In: Journal of the American Chemical Society, Vol. 131, No. 28, 2009, p. 9805-9812.

Research output: Contribution to journalArticleAcademic

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AB - A versatile synthetic strategy has been developed which enables the facile incorporation of cleavable functional groups, i.e., esters, thioesters, and disulfides, into the carbon−carbon backbone of vinyl-based polymers. Through the synthesis of novel cyclic monomers, RAFT-mediated radical ring-opening copolymerizations with traditional vinyl monomers such as methyl methacrylate, N,N-dimethylaminoethyl methacrylate, and 2-hydroxyethyl methacrylate lead to the introduction of controlled degradability into these widely used vinyl copolymer systems. An additional benefit of this strategy is the inherent versatility available through the incorporation of cyclic monomers containing diverse functional groups such as esters, thioesters, disulfides, and silyl ether units that allow degradation under basic/acidic, reductive, or enzymatic conditions. By integrating multiple, orthogonal cyclic monomers into linear copolymer backbones, well-defined systems with programmable degradation profiles are obtained which allows for tunable, selective, and stepwise degradation of the vinyl polymer backbones.

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