Synthesis and properties of a new class of fully conjugated azahexacene analogues.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2014)
摘要
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 3a-d. These molecules are composed of a core of four fused five-membered rings derived from their respective diketopyrrolopyrroles. These new pi-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.
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关键词
acenes,aromaticity,dyes/pigments,fused-ring systems,ring annulation
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