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Thiol‐Ene Click Chemistry as a Tool for a Novel Family of Polymeric Ionic Liquids
Author(s) -
Shaplov Alexander S.,
Vlasov Petr S.,
Lozinskaya Elena I.,
Shishkan Olga A.,
Ponkratov Denis O.,
Malyshkina Inna A.,
Vidal Frédéric,
Wandrey Christine,
Godovikov Ivan A.,
Vygodskii Yakov S.
Publication year - 2012
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201200081
Subject(s) - ionic liquid , monomer , polymer chemistry , chemistry , copolymer , imide , ionic bonding , chloride , click chemistry , ene reaction , polymer , ionic conductivity , thiol , organic chemistry , ion , catalysis , electrode , electrolyte
Functionalized pyrrolidinium compounds, 3‐((2‐hydroxyethylthio)methyl)‐1,1,4‐trimethylpyrrolidinium and 3‐((2‐carboxyethylthio)methyl)‐1,1,4‐trimethylpyrrolidinium chlorides, are prepared from N , N ‐diallyl‐ N , N ‐dimethylammonium chloride by radical thiol‐ene addition and are utilized as building blocks in the synthesis of “ionic liquid‐like monomers.” “Polymeric ionic liquids” with highest molecular weights are obtained in water from chloride monomers followed by ionic exchange with lithium bis(trifluoromethylsulfonyl)imide. Synthesized polymers demonstrate negligible water absorption (<0.1 wt%). Copolymerization with polyethyleneglycol di‐ and monomethacrylates leads to the conductive self‐standing tough films with ionic conductivity up to 2.8 × 10 −7 /1.3 × 10 −6 S cm −1 at 25 °C.