ADMET polymerization of α,ω-unsaturated glycolipids: synthesis and physico-chemical properties of the resulting polymers

Geoffrey Hibert (1) , Etienne Grau (2, 1) , Didier Pintori (3) , Sébastien Lecommandoux (1, 4) , Henri Cramail (5, 2)

1 LCPO - Laboratoire de Chimie des Polymères Organiques
2 Team 2 LCPO : Biopolymers & Bio-sourced Polymers
3 ITERG - Institut des Corps Gras
4 Team 3 LCPO : Polymer Self-Assembly & Life Sciences
5 LCPO - Laboratoire de Chimie des polymères organiques

Trehalose diesters exhibiting α,ω-unsaturation are glycolipids which can be easily polymerized by ADMET (acyclic diene metathesis) polymerization. In this paper, enzymatic esterification was performed to selectively esterify primary hydroxyl groups of trehalose (6 and 6'-positions) with vinyl undecenoate. The vinyl ester was beforehand obtained by palladium-catalyzed transesterification of undecenoic acid with vinyl acetate. The resulting trehalose diundecenoate was homopolymerized and copolymerized with undecenyl undecenoate in order to obtain random copolymers with different compositions. The synthesis of such copolymers was confirmed by 1 H NMR spectroscopy and size exclusion chromatography (SEC). Their solid-state phase separation were investigated by DSC and X-ray scattering as function of temperature and their solution self-assembly was investigated by dynamic light scattering (DLS) in water.

Domaines: Matériaux; Polymères; Science des matériaux [cond-mat.mtrl-sci]

Geoffrey Hibert, Etienne Grau, Didier Pintori, Sébastien Lecommandoux, Henri Cramail. ADMET polymerization of α,ω-unsaturated glycolipids: synthesis and physico-chemical properties of the resulting polymers. Polymer Chemistry, 2017, 24, pp.3731-3739. ⟨10.1039/C7PY00788D⟩. ⟨hal-02367220⟩