Liquid-Phase Enantioselective Chromatographic Resolution Using Interpenetrated, Homochiral Framework Materials

Effective separation of mixtures of enantiomers is of continuing interest in analytical and preparative chromatography, with new materials frequently designed and tested. We report two new enantiomerically pure 2D -> 3D interpenetrated materials used as stationary liquid chromatographic ( LC) phases that are shown to resolve selected racemic mixtures with enantiomeric and chemical selectivity. Dicarboxylate ligands derived from amino acids on naphthalene and perylene cores form 2D frameworks that interpenetrate to give 3D structures. Selectivity is initially tested by uptake from solution; subsequent LC methods show that the materials exhibit resolution of racemic analytes in 'micro-columns' and that the two closely related materials show markedly different selectivity for different analytes with much greater activity than the ligands alone. Comparison with a close-packed analogue suggests that the separation activity is largely due to surface effects.