Electrochemical recognition of chiral species using quaternary ammonium binaphthyl salts

The use of ephedrine-substituted quaternary ammonium binaphthyl salts as molecular receptors is demonstrated. The electrochemical oxidation of the receptor is affected by the binding of an analyte in solution. The binding site on the binaphthyl salt has been determined using computer modeling and confirmed using 1D and 2D NMR studies. It is shown that the sensitivity of the receptor is related to the size of the analyte. Axially chiral binaphthyl salts are shown to bind chiral analytes in a different manner and this is demonstrated using lactic and mandelic acid. The presence of a polar functional group on the analyte is also shown to have an effect on the guest-host interaction.