Amphotropic inositol liquid crystals

Carbohydrates are an attractive class of starting materials for organic syntheses since they are highly functionalized and environmentally sound, in this way promoting a sustainable chemistry. As such, we employ inositols (cyclohexane-1,2,3,4,5,6-hexols e.g. 1 i.e. myo-inositol) for syntheses of new amphiphilic liquid crystalline materials [1,2] and surface active agents [3,4]. Regarding these topics, lyotropic liquid crystals in some way represent a kind of bridging link between the crystalline/thermotropic liquid crystalline phases on the one hand and the solution properties (and surface activity) of the materials on the other. Furthermore, from our point of view lyotropic liquid crystals still do not get the attention they deserve, although this type of organization is very important e.g. in biology and for applications in connection with living systems. The exact nature and influence of the dynamic hydrogen bond network and the hydrophobic effect involved in the formation of the supramolecular architectures in aqueous systems of such amphiphiles are not yet well understood. We therefore started a synthetic and theoretical study on systematically altered new inositol amphiphiles in which two usually differently behaving structural units are chemically linked to form the hydrophilic head group: the carbohydrate unit (inositol) and an oligo(ethylene oxy) unit (cf. rac-5 and rac-6). The resulting amphiphiles rac-5 and rac-6 display an interesting behaviour with respect to their mesomorphic and solution/surface properties. We will present the syntheses and our results related to supramolecular characterization and theoretical models concerning these new inositol derivatives