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Organic semiconductors (ITTI and IDTI) characterized of thieno[3,2-b]thiophene and dithiophene bridged isoindigo derivatives were designed and successfully synthesized. 1H–13C HMBC, 1H–1H nuclear Overhauser enhancement spectroscopy (NOESY) spectra, and 1H nuclear Overhauser enhancement (NOE) experiments were employed to determine the configurations of the synthesized molecules, indicating they belong to stable Z,Z configurations. Organic field-effect transistors based on ITTI and IDTI through a solution processed method have good air stabilities and exhibit hole mobilities of 0.045 and 0.075 cm2 V–1 s–1 after high-temperature annealing in air, respectively.