Premium
Synthesis and Properties of a New Class of Fully Conjugated Azahexacene Analogues
Author(s) -
Yue Wan,
Suraru SabinLucian,
Bialas David,
Müller Matthias,
Würthner Frank
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403227
Subject(s) - conjugated system , molecule , homo/lumo , chemistry , aromaticity , semiconductor , absorption (acoustics) , organic semiconductor , materials science , nanotechnology , organic chemistry , polymer , optoelectronics , composite material
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.