Board-like Fused-Thiophene Liquid Crystals and their Benzene Analogs: Facile Synthesis, Self-Assembly, p-Type Semiconductivity, and Photoluminescence

Fused-thiophene discotic liquid crystals were designed and easily synthesized by Suzuki coupling and FeCl3 oxidized tandem cyclodehydrogenation reactions, including homo- and cross-coupling reactions. The resulting hexagonal and rectangular columnar mesomorphic supramolecular structures formed were characterized by polarizing optical microscopy, differential scanning calorimetry, and small-angle X-ray scattering. The charge carrier transport properties in the mesophases of two of the synthesized fused-thiophene discogens were measured by transient photocurrent time-of-flight (TOF) technique, revealing fast hole transport values in the range of 10(-3) to 10(-2) cm(2) V-1 s(-1), thus demonstrating potential applications in electronic devices. The luminescent sanidic mesogens, with different extended pi-conjugated systems, also emit blue, green, or red light, with absolute photoluminescent quantum yields as high as 18 %.