Helicity: A Non-Conventional Stereogenic Element for Designing Inherently Chiral Ionic Liquids for Electrochemical Enantiodifferentiation

Configurationally stable 5-aza[6]helicene (1) was envisaged as a promising scaffold fornon-conventional ionic liquids (IL)s. It was prepared, purified, and separated into enantiomersby preparative HPLC on a chiral stationary phase. Enantiomerically pure quaternary salts of1with appropriate counterions were prepared and fully characterized.N-octyl-5-aza[6]heliceniumbis triflimidate (2) was tested in very small quantities as a selector in achiral IL media to performpreliminary electrochemical enantiodifferentiation experiments on the antipodes of two differentchiral probes. The new organic salt exhibited outstanding enantioselection performance with respectto these probes, thus opening the way to applications in the enantioselective electroanalysis ofrelevant bioactive molecules.