Protic and aprotic anionic oligomeric ionic liquids

Abstract

We report on synthesis of linear and hyperbranched protic and aprotic anionic oligomeric ionic liquids (OILs). α,ω-Dicarboxy- and α,ω-disulfooligo(ethylene oxide)s, α-carboxy- and α-sulfooligo(ethylene oxide monomethyl ether)s, and di[(α-carboxyoligo(ethylene oxide monomethyl ether)] were synthesized using reaction of oligo(ethylene oxide diol) (MW 1000) and its monomethyl ether (MW 750) with phthalic-, 2-sulfobenzoic anhydride and pyromellitic dianhydride. Di- and mono-substituted anionic OILs were prepared by neutralizing these compounds with N-methylimidazole. Aprotic anionic OILs were synthesized by reaction of sodium salts of the prepared oligomeric di- and monoacids with 1,3-dimethyl imidazolium iodide. Hyperbranched protic and aprotic anionic OILs were prepared in a similar manner. The structure, thermal stability and ionic conductivity of the synthesized compounds in the range of 20–120 °C in anhydrous conditions is governed by the molecular architecture of the oligomeric chains and the type of the cation/anion moieties. OILs under study are amorphous at room temperature but some protic and aprotic linear-chain OILs prone to form a low melting temperature crystalline phase. The ionic conductivity of the synthesized OILs can be varied in broad range reaching 10−3 S/cm value at temperatures over 100 °C under anhydrous conditions.