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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 -3 cm -2 V -1 s -1 range, consistent with the high degree of ordering and stability of the columnar superstructures. One mesogen in particular with benzodithiophen-4,8-dione core shows outstanding ambipolar charge carrier transport with both high electron (μe = 6.6×10 -3 cm -2 V -1 s -1 ) and hole (μh = 4.5×10 -3 cm -2 V -1 s -1 ) mobility values.