Bisthiadiazole-Fused Tetraaza­pentacene­quinone: An Air-Stable Solution-Processable n‑Type Organic Semiconductor

The synthesis and characterization of a tetraaza­pentacene­quinone fused to two thiadiazoles is reported. This linear derivative constituting seven fused rings shows a very low LUMO level (−4.46 eV) and a low HOMO–LUMO gap (1.77 eV). Its high solubility, endowed by four triisopropylsilyl groups, allows the fabrication of air-stable field-effect transistors by liquid deposition methods that show electron mobilities up to 2.42 × 10–3 cm2 V–1 s–1 without any device optimization.本研究报道了一种与两个噻二唑（thiadiazoles）稠合的四氮并五苯醌（tetraazapentacenequinone）的合成与表征。该线性衍生物由七个稠合环构成，其最低未占据分子轨道（Lowest Unoccupied Molecular Orbital，简称LUMO）能级极低（−4.46 eV），且最高占据分子轨道与LUMO之间的能隙仅为1.77 eV。该化合物因带有四个三异丙基硅基（triisopropylsilyl）基团而具备高溶解性，可通过液相沉积法制备得到空气稳定的场效应晶体管（field-effect transistor）；在未进行任何器件优化的前提下，其电子迁移率最高可达2.42 × 10⁻³ cm²·V⁻¹·s⁻¹。