Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals,Chemical Society Reviews

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Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals
Chemical Society Reviews ( IF 40.4 ) Pub Date : 2015-05-21 00:00:00 , DOI: 10.1039/c5cs00051c
Zebing Zeng _{1,

2,

3} , Xueliang Shi _{1,

2,

3} , Chunyan Chi _{1,

2,

3} , Juan T. López Navarrete _{4,

5,

6} , Juan Casado _{4,

5,

6} , Jishan Wu _{1,

2,

3,

7,

8}

Affiliation

Aromaticity is an important concept to understand the stability and physical properties of π-conjugated molecules. Recent studies on pro-aromatic and anti-aromatic molecules revealed their irresistible tendency to become diradicals in the ground state. Diradical character thus becomes another very important concept and it is fundamentally correlated to the physical (optical, electronic and magnetic) properties and chemical reactivity of most of the organic optoelectronic materials. Molecules with distinctive diradical character show unique properties which are very different from those of traditional closed-shell π-conjugated systems, and thus they have many potential applications in organic electronics, spintronics, non-linear optics and energy storage. This critical review first introduces the fundamental electronic structure of Kekulé diradicals within the concepts of anti-aromaticity and pro-aromaticity in the context of Hückel aromaticity and diradical character. Then recent research studies on various stable/persistent diradicaloids based on pro-aromatic and anti-aromatic compounds are summarized and discussed with regard to their synthetic chemistry, physical properties, structure–property relationships and potential material applications. A summary and personal perspective is given at the end.

中文翻译：

亲芳香族和抗芳香族π共轭分子：不可抗拒的希望成为双自由基

芳香性是理解π共轭分子的稳定性和物理性质的重要概念。对前芳香族和抗芳香族分子的最新研究表明，它们在基态上变成双自由基的趋势不可抗拒。因此，双自由基性成为另一个非常重要的概念，并且它与大多数有机光电子材料的物理（光学，电子和磁性）性质和化学反应性基本相关。具有独特的双自由基特性的分子表现出与传统的封闭壳π共轭体系非常不同的独特性能，因此它们在有机电子，自旋电子学，非线性光学和能量存储中具有许多潜在的应用。这篇重要的评论首先在Hückel芳香性和双自由基性的背景下，在反芳香性和亲芳香性的概念中介绍了Kekulé双自由基的基本电子结构。然后，对基于前芳香族和抗芳香族化合物的各种稳定/持久性双基自由基的最新研究进行了总结和讨论，涉及它们的合成化学，物理性质，结构-性质关系以及潜在的材料应用。最后给出了总结和个人观点。然后，对基于前芳香族和抗芳香族化合物的各种稳定/持久性双基自由基的最新研究进行了总结和讨论，涉及它们的合成化学，物理性质，结构-性质关系以及潜在的材料应用。最后给出了总结和个人观点。然后，对基于前芳香族和抗芳香族化合物的各种稳定/持久性双基类胡萝卜素的最新研究进行了总结和讨论，涉及它们的合成化学，物理性质，结构-性质关系以及潜在的材料应用。最后给出了总结和个人观点。

更新日期：2015-05-21

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