Chiral resolution of the enantiomers of phenylglycinol using (S)-di-naphthylprolinol calix[4]arene by capillary electrophoresis and fluorescence spectroscopy

Abstract

We have previously shown that the tetra-(S)-di-2-naphthylprolinol calix[4]arene derivative possesses the ability to provide chiral discrimination between enantiomers of phenylethylamine and norephedrine, using fluorescence quenching experiments and Stern–Volmer plots. In this paper, we demonstrate that the same compound interacts selectively with enantiomers of phenylglycinol, using the same approach. We also show that this chiral discrimination can provide efficient separation of phenylglycinol by capillary electrophoresis through the immobilisation of the calix[4]arene on the capillary wall. The results obtained by both methods suggest that the (R)-phenylglycinol enantiomer interacts more strongly with the chiral calixarene than the (S)-enantiomer.