Chiral glucose-derived surfactants: The effect of stereochemistry on thermotropic and lyotropic phase behavior

Abstract

The two chiral isomers of the surfactant (±)-2-dodecyl β-D-glucoside have been prepared, and their thermotropic and lyotropic liquid crystalline behavior has been studied. Mixtures of the two pure diastereomers were prepared in known ratios to examine the effect of chiral purity on these properties using the techniques of differential scanning calorimetry and polarized light optical microscopy. It was found that the (+)-diastereomer produced crystalline and liquid crystalline phases in the presence and absence of water, which were more thermally stable than the (-)-diastereomer. The transition temperatures were reduced with increasing amounts of the (-)-diastereomer, but eutectic-like behavi..