Liquid-Crystalline Inositol Ethers, their Syntheses and Columnar Mesophases

Abstract

Syntheses of selected multi-O-alkylethers of the stereoisomeric myo- and scyllo-inositols are described. Necessary conversions of axial hydroxyl groups into equatorial ones have been performed with either potassium superoxide (KO₂) or potassium nitrite (KNO₂) as powerful oxygen nucleophiles for this purpose. Most of the novel cyclitol ethers are thermotropic liquid crystals. Depending on the number, positions, and stereochemical arrangement of alkyl chains attached to the inositol core, these biomolecule mesogens, chemically vicinal diols and a tetrol, show interesting modes of molecular organizations in their columnar liquid-crystalline phases. The architectures of these mesophases are based on hydrogen-bridged multimers. Models for their self-assembled “supramolecular structures” are presented and discussed.