Persistent Ambipolar Heptacenes and Their Redox Species

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. T...

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Detalles Bibliográficos
Autores principales: Zeitter, Nico, Hippchen, Nikolai, Maier, Steffen, Rominger, Frank, Dreuw, Andreas, Freudenberg, Jan, Bunz, Uwe H. F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9324111/
https://www.ncbi.nlm.nih.gov/pubmed/35377538
http://dx.doi.org/10.1002/anie.202200918
Descripción
Sumario: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 cm(2) V(−1) s(−1) n‐channel), which was corroborated by generation of its monoanion and monocation.

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