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. In particular, the mesogen with a benzodithiophen-4,8-dione core shows ambipolar charge carrier transport with both high electron (mu(e)=6.6x10(-3) cm(-2) V-1 s(-1)) and hole (mu(h)=4.5x10(-3) cm(-2) V-1 s(-1)) mobility values.

Automated summary

Mesomorphous butterfly-like shape molecules based on benzodithiophene, benzodithiophene-4,8-dione, and cyclopentadithiophen-4-one core moieties were efficiently synthesized and displayed different solvent-gelling and luminescent properties. The compounds showed promising charge carrier mobility in the columnar superstructures, with some exhibiting ambipolar charge carrier transport capabilities.