π-Extended Zigzag-Shaped Diphenanthrene-Based p-Type Semiconductors Exhibiting Small Effective Masses

Molecular design strategy of the pi-electron core is of importance to enhance the organic semiconducting performance. In this study, diphenanthro[1,2-b:2 ',1 '-d]thiophene (DPT) as a new zigzag-shaped sulfur-bridged pi-electron core and its phenyl-substituted derivative (Ph-DPT) exhibiting unique orbital configurations are reported. The DPT derivatives are readily synthesized through a versatile synthetic scheme in five steps from the commercially available dibenzothiophene. Their single-crystal structural analyses and band calculations revealed that both DPTs form typical herringbone packing structures, which are favorable for 2D charge carrier transport, along with small effective masses. Single-crystal-based field-effect transistors (FETs) of both DPT and Ph-DPT exhibit p-type behaviors and charge-carrier mobility up to 5.5 cm(2) V-1 s(-1). These results provide information that can broaden the molecular design approaches toward high-performance organic semiconductors.

Automated summary

This study reported a new zigzag-shaped sulfur-bridged pi-electron core and its derivative, investigated their molecular design strategy and their impact on organic semiconductor performance through single-crystal structural analysis and band calculation.