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Issue 11, 2011
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Design and synthesis of new anionic “polymeric ionic liquids” with high charge delocalization

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Abstract

Three novel ionic monomers having highly delocalized anions and electrochemically stable mobile cations, namely, 1-butyl-1-methylpyrrolidinium 1-[3-(methacryloyloxy)propylsulfonyl]-1-(trifluoromethane-sulfonyl)imide, 1-butyl-1-methylpyrrolidinium 1,1-dicyano-1-[(3-(methacryloyloxy)propylsulfonyl)]methanide and 1-butyl-1-methylpyrrolidinium 1-cyano-1-[(3-(methacryloyloxy)propylsulfonyl)]imide were synthesized and characterized. The structure of these monomers was designed to be a mimic of the most highly conductive bis(trifluoromethylsulfonyl)imide, tricyanomethanide and dicyanamide anions. By radical polymerization procedure a series of new anionic “polymeric ionic liquids” (PILs) were prepared. The solubility of these linear PILs, thermal stability, glass transition temperatures, molar masses and ionic conductivities were estimated. An advantage of the novel PILs was demonstrated by the comparison of their ionic conductivity at 25 °C (2.0 × 10−8 ÷ 1.6 × 10−7 S cm−1) with the unmodified poly(1-ethyl-1-methylpyrrolidinium 3-(methacryloyloxy)propane-1-sulfonate) analog. The increase in ionic conductivity is as high as three orders of magnitude and was found to depend on the size of the attached anion. The new ionic monomers were subsequently copolymerized with poly(ethylene glycol) dimethacrylate and poly(ethylene glycol) methyl ether methacrylate. The investigation of the copolymers properties revealed further improvement of the conductivity in approximately two orders of magnitude and the achievement of σ = 4.8 ÷ 6.8 × 10−6 S cm−1) at 40 °C.

Graphical abstract: Design and synthesis of new anionic “polymeric ionic liquids” with high charge delocalization

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Article information


Submitted
22 Jun 2011
Accepted
13 Jul 2011
First published
25 Aug 2011

Polym. Chem., 2011,2, 2609-2618
Article type
Paper

Design and synthesis of new anionic “polymeric ionic liquids” with high charge delocalization

A. S. Shaplov, P. S. Vlasov, M. Armand, E. I. Lozinskaya, D. O. Ponkratov, I. A. Malyshkina, F. Vidal, O. V. Okatova, G. M. Pavlov, C. Wandrey, I. A. Godovikov and Y. S. Vygodskii, Polym. Chem., 2011, 2, 2609
DOI: 10.1039/C1PY00282A

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