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

Abstract : 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.
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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, Royal Society of Chemistry - RSC, 2016, 7 (45), pp.6901-6910. ⟨10.1039/c6py01004k⟩. ⟨hal-01497309⟩

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