Abstract Sixfold TIPS‐ethynylation combined with fourfold bromination of the armchair edges furnishes a long‐lived, soluble heptacene; π‐extension via Stille coupling accesses a persistent tetrabenzononacene. Both types of acenes were stabilized best by double TIPS‐ethynylation on every other benzene ring. Tetrabromoheptacene is an ambipolar transistor material (up to 0.036?cm2?V?1?s?1 n‐channel), which was corroborated by generation of its monoanion and monocation.
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