The Radical Anion, Dianion and Electron Transport Properties of Tetraiodotetraazapentacene.

Tetraiodotetraazapentacene I 4 TAP, 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 Br 4 TAP. I 4 TAP is an n-channel material in thin-film transistors with average electron mobilities exceeding 1 cm 2 (Vs) -1 .