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 (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. Butterfly‐like mesogens based on benzodithiophene, benzodithiophene‐4,8‐dione and cyclopentadithiophen‐4‐one core moieties were efficiently synthesized by the Suzuki‐Miyaura/Scholl reactions’ tandem. Depending on the core nature and radial aliphatic chains number, they self‐organize into columnar hexagonal mesophase, possess solvent‐gelling ability, emit light in the visible range, and display hole‐transport performances. In particular, the mesogen with benzodithiophen‐4,8‐dione core shows ambipolar charge carrier transport with both high electron and hole mobility values.