Stabilization of Columnar Liquid Crystal Phases via Arene-Perfluoroarene Interactions

Abstract

We report the synthesis of novel polycatenar dibenzopentacenequinones <b>1</b> and <b>2</b> that are designed to form columnar liquid crystalline phases. The mesomorphic properties of these compounds were investigated by polarized optical microscopy, differential scanning calorimetry, and powder X-ray diffraction. While compound <b>1</b> exhibits two distinct columnar mesophases between 148 and 177 °C, fluorinated <b>2</b> exhibits a columnar mesophase from 121 to 336 °C. This dramatic stabilization of the columnar mesophase of <b>2</b> can be attributed to improved π-stacking as a result of arene-perfluoroarene interactions.