Synthesis and properties of a new class of fully conjugated azahexacene analogues.
Synthesis and properties of a new class of fully conjugated azahexacene analogues.
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DOI：
10.1002/anie.201403227
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发表时间：
2014-06
影响因子：
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通讯作者：
W. Yue;Sabin‐Lucian Suraru;D. Bialas;M. Müller;F. Würthner
中科院分区：
文献类型：
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作者：
W. Yue;Sabin‐Lucian Suraru;D. Bialas;M. Müller;F. Würthner
苯是一类传统的多环芳烃(PAHs)，由于其优异的p沟道半导体性质，在过去的十年里引起了人们的极大兴趣。最近，还制备了N-杂二烯。这些分子已经被证明更稳定，并且可以表现出n沟道半导体性质。受这些原型多环芳烃的启发，我们合成了一类新型的高持久性氮杂环己烯类似物3a-d。这些分子是由四个稠合的五元环组成的核心，这些环来自于它们各自的二酮基吡咯。这些新的π共轭支架在可见光区域表现出广泛和强烈的吸收，并具有低水平的HOMO和LUMO水平，导致与并苯和大多数杂苯相比具有更好的稳定性。
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.