Vinyl monomers bearing sulfonyl(trifluoromethane sulfonyl) imide group: synthesis and polymerization using nitroxide-mediated polymerization

Trang N. T. Phan (1) , Adèle Ferrand (1) , Hien The Ho (1) , Livie Liénafa (1) , Marion Rollet (1) , Sébastien Maria (1) , Renaud Bouchet (2) , Didier Gigmes (1)

1 ICR - Institut de Chimie Radicalaire
2 LEPMI - Laboratoire d'Electrochimie et de Physico-chimie des Matériaux et des Interfaces

A series of water-soluble styrene and propyl (meth)acrylate based monomers bearing a sulfonyl(trifluoromethane sulfonyl) imide (STFSI) group was prepared. These monomers were synthesized in good yield from the corresponding chloride sulfonyl monomer and trifluoromethanesulfonamide. Their chemical structures were further confirmed by HR-MS and NMR spectroscopy. Nitroxide-mediated polymerization of the prepared monomers was then performed in aqueous solution at 100 °C, 90 °C and 75 °C for acrylate, styrene and methacrylate derivatives, respectively. Controlled polymerization was successfully achieved as illustrated by the linearity of ln([M]0/[M]) vs. t2/3, the molar mass increase with conversion and the relatively low dispersity values for the resulting homopolymers. Compared to their neutral analogous polymers, the prepared anionic homopolymers exhibited a higher glass-transition temperature. This phenomenon was attributed to the electrostatic interactions between STFSI side groups along the polymer backbone.

Keywords: vinyl; polymerization; monomers

Domains: Chemical Sciences; Polymers

Trang N. T. Phan, Adèle Ferrand, Hien The Ho, Livie Liénafa, Marion Rollet, et al.. Vinyl monomers bearing sulfonyl(trifluoromethane sulfonyl) imide group: synthesis and polymerization using nitroxide-mediated polymerization. Polymer Chemistry, 2016, 7 (45), pp.6901-6910. ⟨10.1039/c6py01004k⟩. ⟨hal-01497309⟩