title: Synthesis and properties of a new class of fully conjugated azahexacene analogues.
abstract: Acenes are a traditional class of polycyclic aromatic hydrocarbons (PAHs) which attracted considerable interest during the last decade because of their outstanding p-channel semiconductor properties. More recently, N-heteroacenes have been prepared. These molecules have been shown to be more stable and can exhibit n-channel semiconductor properties. Inspired by these archetype PAHs, we synthesized a novel class of highly persistent azahexacene analogues 3 a-d. These molecules are composed of a core of four fused five-membered rings derived from their respective diketopyrrolopyrroles. These new π-conjugated scaffolds show broad and intense absorption in the visible region and possess low-lying HOMO and LUMO levels, leading to much better stability compared to that of acenes and most heteroacenes.
authors.affiliation: Universität Würzburg, Institut für Organische Chemie & Center for Nanosystems Chemistry, Am Hubland, 97074 Würzburg (Germany).
authors.forename: Wan
authors.initials: W
authors.lastname: Yue
authors.forename: Sabin-Lucian
authors.initials: SL
authors.lastname: Suraru
authors.forename: David
authors.initials: D
authors.lastname: Bialas
authors.forename: Matthias
authors.initials: M
authors.lastname: Müller
authors.forename: Frank
authors.initials: F
authors.lastname: Würthner
keywords: acenes; aromaticity; dyes/pigments; fused-ring systems; ring annulation