Molecular packing handedness dominated by the chirality of the lactic acid residue near the liquid crystalline core

Eight dichiral compounds containing two lactic acid residues and one perfluorocarbon chain are synthesised. Six of them are liquid crystals with an enantiotropic SmA phase. Two of them are liquid crystals with enantiotropic SmA and SmC* phases. Although (R,R)-3 and (R,R)-4 molecules pack in monolayer structures at the crystalline states, (S,R)-3 and (R,S)-4 molecules pack in bilayer structures at the crystalline states. The optical activity of these compounds is mainly controlled by the chirality of the lactic acid residue near the liquid crystalline core. The dichiral compounds can self-assemble into nanotubes or twisted nanoribbons in methanol. Circular dichroism characterisation indicated that the stacking handedness of the liquid crystalline cores in the organic self-assemblies was also dominated by the chirality of the lactic acid residue near the liquid crystalline core.