Synthesis and Physicochemical Properties of Piceno[4,3-b:9,10-b′]dithiophene Derivatives and Their Application in Organic Field-Effect Transistors

Efficient synthesis and characterization of several piceno[4,3-b:9,10-b′]dithiophene (PiDT) derivatives by Negishi coupling, epoxidation, and Lewis acid-catalyzed cycloaromatization sequences and their potential utility in organic field-effect transistors (OFETs) have been reported. PiDT derivatives, with extended π-electron systems, showed high air stability due to their deep highest occupied molecular orbital energy levels (around −5.6 eV). OFET devices based on 2,11-dioctylated PiDT (C8-PiDT) showed excellent hole mobility, as high as 2.36 cm2 V–1 s–1. Their structure–property relationships were investigated by X-ray diffraction and atomic force microscopy.