Synthesis of well-designed polymers carrying saccharide moieties via RAFT miniemulsion polymerization

Two hydrophobic vinyl saccharide monomers based on D-glucose and D-fructose were polymerized by employing the reversible addition-fragmentation transfer (RAFT) miniemulsion polymerization technique to prepare well-designed glycopolymers. Three dithiobenzoate-RAFT agents [S=C(Ph)S-R], 1-phenylethyl dithiobenzoate (PED), 2-phenylprop-2-yl dithiobenzoate (PPD), and 2-cyanoprop-2-yl dithiobenzoate (CPD), were used to control the growth of polymer chains. The best results were obtained in the presence of the PPD-RAFT agent and the formed polymers have polydispersity index's (PDI) lower than 1.15. Under adequate miniemulsion polymerization conditions, a glyco-polymer with PDI of 1.1 and molecular weight of 5 X 10(4) g/mol has been successfully synthesized in a short reaction time of 100 min. Furthermore, some block copolymers containing saccharide segment with butyl or methyl methacrylate were prepared. Copyright (C) 2007 John Wiley & Sons, Ltd.