Divergent Synthesis and Semiconductor Properties of Dithienobenzothiazoles with S•••N and S•••S Interactions Controlling Molecular Arrangement in Crystal

Abstract

Seven dithienobenzothiazole (DBT) derivatives 1a–g were synthesized by one-step functionalization of a common precursor and investigated for their semiconducting properties. The DBT core possesses a three-directional annulated -conjugated plane which enables variable intermolecular interaction, such as S•••S and S•••N interactions. X-ray single-crystal structural analyses confirmed that the molecular arrangements of 1b (the diethyl and ethylthienyl derivative) and 1c (the di(n-propyl) and n-propylthienyl derivative) in the crystal are classified into brickwork structures with multidirectional intermolecular charge-transfer integrals. The solution-processed top-gate bottom-contact devices of 1b and 1c had moderate hole mobilities of 0.16 and 0.029 cm2 V–1s–1, respectively.