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.

本文报道了一种与两个噻二唑（thiadiazoles）稠合的四氮杂并五苯醌（tetraazapentacenequinone）的合成与表征。该含七个稠合环的线性衍生物展现出极低的最低未占据分子轨道（Lowest Unoccupied Molecular Orbital，LUMO）能级（-4.46 eV），以及较窄的最高占据分子轨道（Highest Occupied Molecular Orbital，HOMO）-LUMO能隙（1.77 eV）。其凭借四个三异丙基硅基（triisopropylsilyl）基团赋予的高溶解性，可通过液相沉积法制备空气稳定的场效应晶体管；该器件无需任何器件优化，即可实现最高达2.42 × 10^–3 cm²·V^–1·s^–1的电子迁移率。