To investigate a hybrid of isoindigo and thienoisoindigo (TIIG), a new series of unsym. TIIG analogs, in which one of the outer thiophene rings of TIIG is replaced by benzene (CS) or pyridine (NS) are prepd. In addn., the π-skeleton extension effects are studied by examg. α-substituted TIIG derivs. with thienyl (Dth-TIIG), furyl (Dfu-TIIG), and 1-phenyl-5-pyrazolyl groups (Bis(1-ph-5-py)-TIIG). These materials exhibit ambipolar transistor properties as expected from the energy levels. Dth-TIIG and Dfu-TIIG show hole mobilities exceeding 0.05 cm2 V-1 s-1, and electron mobilities about 0.04 cm2 V-1 s-1, which are close to those of the di-Ph deriv. These mols. are arranged nearly perpendicularly to the substrates in the thin films, and Dth-TIIG has a brickwork-like structure, whereas Dfu-TIIG has uniform columns. CS and Bis(1-ph-5-py)-TIIG have uniform stacking structures, but NS has a dimerized stacking structure due to the slightly bent mol. plane that results from largely unbalanced electron d. [on SciFinder(R)]
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