1-Alkyl-3-methylbenzotriazolium salts: ionic solvents and electrolytes†
A series of 1-alkyl-3-methylbenzotriazolium halides were synthesised and purified by recrystallisation. Novel salts of these benzotriazolium cations were obtained by metathesis with a number of diverse anions including: dicyanamide N(CN)2, mesylate CH3SO3, tosylate CH3C6H4SO3 and bis(trifluoromethane)sulfonamide N(SO2CF3)2. Thermal analyses of these very stable salts included the determination of glass transition temperatures (−65 to −12 °C), melting points (29 to 143 °C), entropies of fusion (14 to 69 J K−1 mol−1) and decomposition temperatures (up to 315 °C). Electrochemical analyses show electrochemical windows of up to ≈3.5 V, the cation producing electrochemical reduction reactions below −1 V (Ag/Ag+). Solubility data for a range of organic compounds dissolved in the new ionic liquids and for comparison in some more common ionic liquids are also provided.