Columnar mesophase from a new disclike mesogen based on a 3,5-dicyano-2,4,6-tristyrylpyridine core

We report on the design and synthesis of a new disclike mesogen based on a 3,5-dicyano-2,4,6-tristyrylpyridine core. This compound was characterized by spectroscopic methods (NMR, UV-vis, and photoluminescence) and cyclic voltammetry. The mesogenic behavior was investigated by differential scanning calorimetry, polarized-light optical microscopy, and X-ray diffraction. The disclike structure self-assembles into a hexagonal columnar mesophase and, because of the permanent dipole exhibited by the isolated molecule, the stacking along the columnar axis is antiparallel. Besides two-dimensional charge transfer and fluorescence, the disclike molecule exhibits high electron affinity as a result of the strong acceptor character of the 3,5-dicyanopyridine core.