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Para-Quinodimethanes: A Unified Review of the Quinoidal-Versus-Aromatic Competition and its Implications
Topics in Current Chemistry ( IF 8.6 ) Pub Date : 2017-07-31 , DOI: 10.1007/s41061-017-0163-2
Juan Casado

In this article, some quinoidal p-quinodimethanes compounds that convert partially or completely to diradicals or biradicaloids are analyzed. The aromatic/quinoidal balance is revisited with the objective of providing a common interpretation for most of them. For that purpose, important structural and energetic parameters such as the bond length alternation pattern and the singlet–triplet gaps are analyzed and interpreted in the framework of double spin polarization and π-conjugation. p-Quinodimethanes based in oligothiophenes, polycyclic aromatic hydrocarbons, oligophenylenes, thienothiophenes, charged dications and cyclic conjugated molecules are discussed. There are excellent reviews in the field of singlet diradicals; however, a revision similar to that proposed here can help the reader to have another perspective on these promising new functional materials. The focus has been put on molecules which are well known by the author and another of relevance in the field. In this regard, the article finishes with a discussion of some important applications of these diradicals in organic electronics. New chemical systems based on the p-quinodimethane building blocks are waiting us around the corner, bringing us new and challenging structures and fascinating novel properties, which describe a very rich field of research in chemistry and in physics with an excellent present and a bright future.



中文翻译:

帕拉-喹啉甲烷:对喹啉对芳香族竞争的统一评价及其启示

在本文中,分析了一些部分或完全转化为双基或双基的对苯二醌化合物。芳香族/喹啉类化合物的平衡被重新研究,目的是为它们中的大多数提供一个通用的解释。为此,在双自旋极化和π共轭的框架内分析和解释了重要的结构和能量参数,例如键长交替模式和单重态-三重态间隙。p讨论了基于低聚噻吩,多环芳烃,低聚苯撑,噻吩并噻吩,带电指示剂和环状共轭分子的喹啉甲烷。在单重双基自由基领域有很好的评论。但是,类似于此处建议的修订版可以帮助读者对这些有前途的新功能材料有另一种看法。焦点集中在作者所熟知的分子以及与本领域相关的另一分子上。在这方面,本文最后讨论了这些自由基在有机电子学中的一些重要应用。基于p的新化学系统-quinodimethane的构建基块正等着我们到来,为我们带来了新的具有挑战性的结构以及令人着迷的新颖特性,这些特性描述了化学和物理领域非常丰富的研究领域,具有出色的现在和广阔的前景。

更新日期:2017-07-31
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