Synthesis and characterization of novel dibenz[a,c]anthracenedicarboxythioimides: the effect of thionation on self-assembly

Abstract

We report the synthesis and properties of a series of novel dibenzanthracenedicarboxythioimides and an investigation of the effects of thionation on self-assembly in these systems. These compounds all display columnar mesophases over broad temperature ranges and self-associate to form dimers in solution. Overall, thionation slightly improves self-assembly in these systems. Furthermore, increasing the thionation of these materials leads to a lowering of the LUMO energy and a narrowing of the HOMO–LUMO band gap.