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