Liquid crystals derived from 2-phenylisoindoles: synthesis and characterization

2-Phenylisoindole was investigated as the rigid core unit in a series of asymmetric mesogenic molecules. When the 2-phenylisoindole core was terminated with a hexyl tail, no mesophase formation could be observed. When 4-n-(tridecafluorohexyl) was used, however, both monotropic and enantiotropic phase behaviour were observed. It was found that most functionalities at the anhydride 5-position results in the formation of smectic A (SmA) phases in the temperature range 70-180°C. Functionalities at the anhydride 4-position suppress mesophase formation. Large substituents (-Br, -NO2) and symmetric substitution patterns (5,6-dichloro, 4,7-dichloro and 4,5,6,7-tetrachloro) on the anhydride moiety increase the melting point and destabilize the mesophase. Temperature dependent X-ray diffraction experiments suggest an interdigitated SmA packing for this family of compounds.