Thiol-functionalized block copolymer vesicles

J. Rosselgong, A. Blanazs, P. Chambon, M. Williams, M. Semsarilar, Peter Jeppe Madsen, G. Battaglia, S. P. Armes*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Thiol-functionalized block copolymer vesicles are readily prepared via RAFT-mediated polymerizationinduced self-assembly (PISA). More specifically, a disulfidefunctionalized poly(glycerol monomethacrylate) macro-CTA is chain-extended using 2-hydroxypropyl methacrylate): the growing water-insoluble poly(2-hydroxypropyl methacrylate) chains drive in situ self-assembly to produce diblock copolymer vesicles in concentrated aqueous solution. The disulfide bonds in the poly(glycerol monomethacrylate) stabilizer chains are reductively cleaved in situ using either tributyl phosphine or tris(2-carboxyethyl)phosphine to generate thiol groups, which react immediately with either a quaternary acrylate to introduce cationic character or with rhodamine B acrylate or rhodamine B isothiocyanate to confer a convenient fluorescent tag. In addition to such facile derivatization, such thiol-functionalized vesicles may offer some potential for drug delivery applications, because enhanced muco-adhesion is anticipated for these nano-objects.

Original languageEnglish
JournalACS Macro Letters
Volume1
Issue number8
Pages (from-to)1041-1045
ISSN2161-1653
DOIs
Publication statusPublished - 2012
Externally publishedYes

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