2,8‑Diphenylbenzo[1,2‑b:4,5‑b']bis[b]benzothiophene: A New Thienoacene Derivative for Potential Organic Electronic Applications.

This work reports the synthesis and comprehensive characterization of 2,8-diphenylbenzo-[1,2-b:4,5-b']-bis-[b]-benzothiophene (diPh-BBBT), a novel thienoacene derivative designed for organic electronic applications. The compound was synthesized from 1,4-dibromo-2,5-bis-(methylsulfinyl)-benzene via Suzuki-Miyaura cross-coupling reaction, followed by double intramolecular cyclization and demethylation. diPh-BBBT demonstrates high thermal stability, pronounced crystallinity, and enhanced resistance to oxidative degradation. In comparison to the benchmark semiconductor 2,7-diphenylbenzothieno-[3,2-b]-benzothiophene (diPh-BTBT), diPh-BBBT exhibits a lower hole reorganization energy (λh = 0.25 eV), which indicates enhanced hole-transport properties. Charge-transport simulations based on a simplified packing model consistent with XRD data for a mechanically oriented film predict hole mobilities of up to approximately 0.5 cm2 V-1 s-1.