Novel thiophene-substituted tetrathia[22]annulenes[2,1,2,1]: synthesis,physical properties,and improvement in field-effect behavior

Novel conjugated macrocycles, thiophene-substituting tetrathia22]annulenes2,1,2,1] (TTAs, and 5b), were synthesized through a convenient four-step procedure. They were evidenced to have high aromaticity by NMR, UV–vis absorption spectra, and calculation. Their UV–vis absorption spectra, thermal stability, electrochemical properties, thin film morphology were studied and the field-effect transistors based on 5a and 5b through a vapor deposition method performed good with reproducible bulk-like carrier mobilities (as high as 0.53 cm² V⁻¹ S⁻¹) and high on/off ratios (as high as 9.0×10⁵), which was among the best records in this series.