Azulene–Pyridine-Fused Heteroaromatics,Journal of the American Chemical Society

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Azulene–Pyridine-Fused Heteroaromatics
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-07-27 , DOI: 10.1021/jacs.0c06299
Hanshen Xin ₁ , Jing Li ₂ , Ru-Qiang Lu ₁ , Xike Gao ₂ , Timothy M Swager ₁

Affiliation

Azulene, a nonbenzenoid bicyclic aromatic hydrocarbon with unique electronic structure, is a promising building block for constructing nonbenzenoid π-conjugated systems. However, azulene-fused (hetero)aromatics remain rare as a result of limited synthetic methods. We report herein the unexpected synthesis of azulene- and pyridine-fused heteroaromatics Az-Py-1, a seven fused ring system with 30π electrons, by reductive cyclization of a 1-nitroazulene. The structure of Az-Py-1 was unambiguously confirmed by single-crystal X-ray analysis, and analogues Az-Py-2-Az-Py-6 were also synthesized, demonstrating that this is an effective method for constructing azulene- and pyridine-fused heteroaromatics. Theoretical calculations and photophysical and electrochemical studies of Az-Py-1-Az-Py-6 suggest their potential as semiconductors, and the single-crystal ribbons of Az-Py-1 show high hole mobilities up to 0.29 cm2 V-1 s-1.

中文翻译：

氮杂-吡啶稠合的杂芳烃

Azulene 是一种具有独特电子结构的非苯型双环芳烃，是构建非苯型 π 共轭系统的有前途的基石。然而，由于合成方法有限，氮杂（杂）芳烃仍然很少见。我们在本文中报告了通过 1-硝基芴的还原环化，意外合成了薁和吡啶稠合的杂芳烃 Az-Py-1，这是一种具有 30π 电子的七稠环系统。单晶X射线分析明确证实了Az-Py-1的结构，并合成了类似物Az-Py-2-Az-Py-6，证明这是一种构建芴和吡啶的有效方法-稠合的杂芳烃。Az-Py-1-Az-Py-6 的理论计算和光物理和电化学研究表明它们具有作为半导体的潜力，

更新日期：2020-07-27

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