Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety

Abstract

A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R' on the 4,6-Oylidene ß-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R' for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.