SYNTHESIS AND LIQUID-CRYSTALLINE PROPERTIES OF MYOINOSITOL AND SCYLLO-INOSITOL MULTI ETHERS

Selectively alkylated myo- and scyllo-inositol ethers were obtained by multi-step syntheses starting from commercially available myo-inositol. Necessary conversions of axial hydroxy groups into equatorial ones were achieved using either potassium superoxide (KO2) or potassium nitrite (KNO2) as oxygen nucleophiles for the transformation of myo- into scylloinositol derivatives. Polarizing microscopic and thermoanalytical studies of numerous members of three families (6, 13, and 20) of inositol ethers reveal for most of them thermotropic liquid-crystalline behavior. Furthermore, in case of the two long-chain scyllitol tetraethers 13d and e an unusual thermopolymorphism has been found. The number, position, and stereochemical arrangement of alkyl chains attached to the inositol cores strongly influence the mesogenic properties of these biomolecule derivatives, chemically vicinal diols and tetrols. The self-assembly of the studied inositol multi ethers to columnar mesophases of ''supramolecular structures'' is discussed considering geometrical features of these molecules and their capabilities to aggregate by hydrogen bonding.