Enantioselective adsorption of surfactants monitored by ATR-FTIR

The selectivity of adsorption of chiral surfactants to a chiral monolayer at the solid-liquid interface was studied using attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR). One enantiomer of the chiral surfactant was deuterated, which causes a change in the IR absorption frequency, and allows independent measurement of the adsorption of each molecule. Both the surfactant, N-lauroyl phenylalanine (NLP), and the chiral monolayer, N-L-phenylalaninoyl, 11-undecyl-silicon, were amino acid derivatives. An enantiomeric excess of 56 +/- 22% of the L over D was observed for adsorption to the interface between a carbon tetrachloride solution containing a quasi-racemate of N-lauroyl phenylalanine and the N-L-phenylalaninoyl, 11-undecyl monolayer film on silicon. In contrast, equimolar adsorption occurred from an equimolar mixture of hydrogenated and deuterated forms of the L surfactant. The measured enantiomeric excess strongly depended on the density of chiral surface groups: the higher the density of chiral groups on the surface, the better the enantiodiscrimination, even though the total adsorption was roughly constant. This nonlinear behavior indicates that more than one chiral surface group is required for significant selectivity.