Development of Low-Molecular-Weight Organogelators from Cyclic β-Amino Acid: Effect of Stereochemistry and their Application on Visual Chiral Recognition of Amines.

Abstract

This study reports the formation of low-molecular-weight gelators based on carboxylic acids derived from chiral cyclicβ-amino acids. The effect of their stereochemistry on the gelation of organic solvents was investigated, and their assemblies with the intermolecular interactions in the xerogels were proposed via infrared spectroscopy, X-ray diffraction, scanning electron microscopy, and crystallographic details of the related model compounds. The effect of the alkyl chain length on the gelators was studied, and they were applied to the chiral recognition of amines. Only one diastereomeric salt with amines afforded gels, whereas the others resulted in precipitates. Chiral recognition was also achieved in the gel state, and the appearance of the as-prepared gel changed upon the addition of each amine enantiomer, thus enabling the visual detection of their chirality.