Persistent Ambipolar Heptacenes and Their Redox Species
Nico Zeitter, Nikolai Hippchen, Steffen Maier, Frank Röminger, Andreas Dreuw, Jan Freudenberg, Uwe H. F. Bunz
Abstract
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 cm 2 V −1 s −1 n‐channel), which was corroborated by generation of its monoanion and monocation.
Topics & Concepts
Ambipolar diffusionStille reactionChemistryRedoxRing (chemistry)NanotechnologyMaterials scienceInorganic chemistryPhysicsOrganic chemistryQuantum mechanicsPlasmaPolymerOrganic Electronics and PhotovoltaicsSynthesis and Properties of Aromatic CompoundsMolecular Junctions and Nanostructures