Carbohydrate-based amphiphilic diblock copolymers: Synthesis, characterization, and aqueous properties

Fabian Suriano, Olivier Coulembier, Philippe Degée, Philippe Dubois

Research output: Contribution to journalArticlepeer-review

Abstract

Amphophilic poly(ε-caprolactone)-b-poly[(methacrylate-graft- poly(ethylene oxide))-co-6-O-methacryloyl-D-galactopyranose] (PCL-b-P(MAPEO-co-GaMa)) with various compositions and molecular weights were synthesized via a controlled four-step strategy. The first step involves the synthesis of functionalized poly(ε-caprolactone) macroinitiator by ring-opening polymerization (ROP) of ε-caprolactone (CL) as initiated by aluminum triisopropoxide (Al(OiPr)3). After selective bromination of the hydroxyl end-group of the resulting α-isopropoxy, ω-hydroxy poly(ε-caprolactone) by using 2-bromoisobutyryl bromide, the controlled radical copolymerization of α-methoxy, ω-methacrylate poly(ethylene oxide) (MAPEO) with 6-O-methacryloyl-1,2;3,4-di-O-isopropylidene- D-galactopyranose (DIGaMa) was performed by atom transfer radical polymerization (ATRP) in THF at 60 °C using CuBr ligated with 1,1,4,7,10,10 hexamethyltriethylenetetramine (HMTETA) as catalytic complex. In the final step, isopropylidene protective functions were selectively removed using an aqueous formic acid solution leading to the expected amphiphilic graft copolymers. The molecular characterization of those copolymers was performed by 1H NMR spectroscopy and gel permeation chromatography (GPC) analysis. The self-assembly of the copolymers into micellar aggregates as well as the related critical micellization concentration (CMC) in aqueous media were determined by dynamic light scattering (DLS) and fluorescence spectroscopy, respectively. In parallel, the morphology of the solid deposits of micellar aggregates was examined with atomic force microscopy (AFM).

Original languageEnglish
Pages (from-to)3662-3672
Number of pages11
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume46
Issue number11
DOIs
Publication statusPublished - 1 Jun 2008
Externally publishedYes

Keywords

  • Amphiphilic
  • ATRP
  • Block copolymer
  • Glycopolymer
  • ROP

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