Abstract
TQPP (X=H): μ=2.5×10−3cm2/Vs. TQPP (X=CH3): μ=7×10−5cm2/Vs. [Display omitted]
•TQPP materials with thermal stability up to 370°C were synthesized.•TQPP and TQPP-[CH3]4 show interplanar stacking distances of 3.4Å using X-ray crystallography.•OTFT field-effect mobilities of 10−3cm2/V−1s−1 for TQPP and 10−5cm2/V−1s−1TQPP-[CH3]4.•Modeling confirms higher electronic coupling constants for TQPP than TQPP-[CH3]4.
Two p-type semiconducting azapyrenoacene materials, quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (TQPP) and 6,7,15,16-tetramethylquinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (TQPP-[CH3]4), were characterized and were found to display high thermal stability and planar molecular geometry as revealed by single-crystal X-ray analysis. In bottom-gate p-channel organic thin-film transistors, field-effect mobilities of 2.5×10−3cm2/Vs and 7.5×10−5cm2/Vs were measured in ambient air for TQPP and TQPP-[CH3]4, respectively. Computational results of reorganization energies and electronic couplings indicate larger inter and intra-columnar couplings for TQPP-[CH3]4 in comparison to TQPP and predict the suitability of both semiconductors for hole as well as electron transporters.