Abstract
Sixteen imidazolium based chiral ionic liquids (CILs) containing Br− and BF4− anions, derived from both enantiomers of phenylethylamine, were synthesized. The imidazole ring was constructed through a condensation reaction of formaldehyde, glyoxal and ammonium hydroxide in aqueous media resulting in a simple, versatile and environmentally friendly protocol. The CILs were synthesized with propyl, butyl, pentyl or hexyl alkyl substituents, which provoke a change of the physicochemical properties that were evaluated (glass transition temperature, thermal stability, optical rotation, ionic conductivity, electrochemical window and toxicity). The 1-alkyl-3-(1-phenylethyl) imidazolium tetrafluoroborate ([Cnpeim]BF4) family showed good thermal stability, large electrochemical window, low toxicity at moderate concentrations, and adequate viscosity. Therefore, these CILs are a good candidates to be used in asymmetric reactions and may be a viable alternative to organic solvents.
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