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

High Resolution Image Download MS PowerPoint Slide 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 (λ h = 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 cm 2 V –1 s –1 .