Butterfly-like Shape Liquid Crystals Based Fused-Thiophene as Unidimensional Ambipolar Organic Semiconductors with High Mobility.

Mesomorphous butterfly-like shape molecules based on benzodithiophene, benzodithiophene-4,8-dione and cyclopentadithiophen-4-one core moieties were efficiently synthesized by the Suzuki-Miyaura coupling and Scholl oxidative cyclo-dehydrogenation reactions' tandem. Most of the butterfly molecules spontaneously self-organize into columnar hexagonal mesophase. The electron-deficient systems possess strong solvent-gelling ability but are not luminescent, whereas the electron-rich terms do not form gels but strongly emit light between 400 and 600 nm. The charge carrier mobility was also measured by time-of-flight transient photocurrent technique in the mesophases for some of the compounds. They display hole-transport performances with positive charge mobility in the 10  cm  V  s range, consistent with the high degree of ordering and stability of the columnar superstructures. In particular, the mesogen with a benzodithiophen-4,8-dione core shows ambipolar charge carrier transport with both high electron (μ =6.6×10  cm  V  s ) and hole (μ =4.5×10  cm  V  s ) mobility values.