The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene

Abstract

Tetraiodotetraazapentacene I4TAP, the last missing derivative in the series of halogenated silylated tetraazapentacenes, was synthesized via condensation chemistry from a TIPS-ethynylated diaminobenzothiadiazol in three steps. Single and double reduction furnished its air-stable monoanion and relatively air-stable dianion, both of which were characterized by crystallography. All three species are structurally and spectroscopically compared to non-halogenated TAP and Br4TAP. I4TAP is an n-channel material in thin-film transistors with average electron mobilities exceeding 1 cm2 (Vs)−1.