A highly π-stacked organic semiconductor for field-effect transistors based on linearly condensed pentathienoacene

We present the synthesis and characterization of a fused-ring compound, dithieno[2,3-d:2′,3′-d]thieno[3,2-b:4,5-b′]dithiophene (pentathienoacene, PTA). In contrast to pentacene, PTA has a larger band gap than most semiconductors used in organic field-effect transistors (OFETs) and therefore is expected to be stable in air. The large π-conjugated and planar molecular structure of PTA would also form higher molecular orders that are conductive for carrier transport. X-ray diffraction and atomic force microscopy experiments on its films show that the molecules stack in layers with their long axis upright from the surface. X-ray photoelectron spectroscopy suggests that there are no chemical bonds at the PTA/Au interface. OFETs based on the PTA have been constructed, and their performances as p-type semiconductors are also presented. A high mobility of 0.045 cm2/V s and an on/off ratio of 103 for a PTA OFET have been achieved, demonstrating the potential of PTA for application in future organic electronics. © 2005 American Chemical Society.