2,12-Diaza[6]helicene: An Efficient Non-Conventional Stereogenic Scaffold for Enantioselective Electrochemical Interphases

The new configurationally stable, unsymmetrical 2,12-diaza[6]helicene was synthesized as a racemate and the enantiomers were separated in an enantiopure state by semi-preparative HPLC on chiral stationary phase. Under selected alkylation conditions it possible to obtain both 2-N-mono- di-N-ethyl quaternary iodides. Metathesis with bis(trifluoromethanesulfonyl)imide anion gave low-melting salts which tested inherently additives achiral ionic liquids for electrochemical enantiodiscrimination of organic probes voltammetric experiments. Remarkable differences oxidation potentials two probes, ferrocenyl amine aminoacid, achieved; increase increasing additive concentration number alkylated nitrogen atoms.