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We have coupled methyl α-d-glucoside (G) and methyl α-d-mannoside (M) as the chiral structural variant moieties in the core and at the branching sites within dendritic scaffolds surrounded by 12 cyanobiphenyl mesogens (CB). Systematic studies of the influence of the chiral moieties on thermal and mesomorphic properties were carried out by positional permutation approach of the pyranose units G and M within the core and branching points. The mesomorphic properties of the chirally homogeneous dendrimers GG/MM and the corresponding chirally heterogeneous dendritic homologues GM/MG were investigated by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). Remarkably, the thermal profile and the mesophase structure of the four dendrimers appear to be significantly independent of the nature of the central chiral core. The outer chirality at the periphery significantly dominates the liquid crystalline properties.