Well-defined glycopolymers from RAFT polymerization: Poly(methyl 6-O-methacryloyl-α-D-glucoside) and Its Block Copolymer with 2-Hydroxyethyl Methacrylate

Luca Albertin, Martina Stenzel, Christopher Barner-Kowollik, L. John R. Foster, Thomas P. Davis

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137 Citations (Scopus)

Abstract

The glycomonomer methyl 6-O-methacryloyl-α-D-glucoside was prepared by lipase-catalyzed transesterification of vinyl methacrylate with methyl α-D-glucoside in dry acetonitrile. The desired 6-O regioisomer was obtained in good yield and its structure confirmed by 1H- 1H and 1H-13C correlation NMR spectroscopy. Reversible addition-fragmentation chain transfer (RAFT) polymerization of the unprotected monomer was performed directly in aqueous solution using (4-cyanopentanoic acid)-4-dithiobenzoate as the chain transfer agent to give poly(methyl 6-O-methacryloyl-α-D-glucoside) with Mn between 16 and 103 kDa (1H NMR) and polydispersities as low as 1.10. Chain extension of one of these polymers with 2-hydroxyethyl methacrylate afforded the novel hydrophilic-hydrophilic block copolymer poly [(methyl 6-O-methacryloyl-α-D-glucoside)-block-(2-hydroxyethyl methacrylate)].

Original languageEnglish
Pages (from-to)7530-7537
Number of pages8
JournalMacromolecules
Volume37
Issue number20
DOIs
Publication statusPublished - 5 Oct 2004
Externally publishedYes

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