An "inherently chiral" 1,1 '-bibenzimidazolium additive for enantioselective voltammetry in ionic liquid media

A dialkyl-1,1'-bibenzimidazolium salt, consisting of an atropisomeric dication (i.e. featuring a stereogenic axis and thus "inherently chiral") and an achiral counteranion, is employed as a chiral additive in three commercial ionic liquids, providing successful enantiodiscrimination in voltammetry experiments on screen-printed electrodes (SPEs) with the enantiomers of N,N'-dimethyl-1-ferrocenyl-ethylamine as model chiral probes. Significant differences in redox potentials are observed for the probe enantiomers despite the low concentration (0.01 M) of the chiral additive. The nature of the achiral ionic liquid in which the additive is employed significantly affects the peak potentials and potential differences, but does not alter the enantiomer sequence.