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

ABSTRACT

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.

Graphical abstract

KEYWORDS:

• Perfluoroalkyl
• liquid crystal
• dichiral
• lactic acid
• self-assembly

Acknowledgments

This work was supported by the Political Science-preponderant Discipline of Jiangsu Province, the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201905) and the National Natural Science Foundation of China (No. 51673141).

Disclosure statement

No potential conflict of interest was reported by authors.

Additional information

Funding

This work was supported by the Political Science-preponderant Discipline of Jiangsu Province, the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201905) and the National Natural Science Foundation of China (No. 51673141).