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Para-Quinodimethanes: A Unified Review of the Quinoidal-Versus-Aromatic Competition and its Implications

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Abstract

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.

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Acknowledgements

The author wishes to acknowledge many of his collaborators at the University of Málaga and many other bright organic chemists who have provided beautiful p-QDM molecules in the last 20 years. A number of institutions are also acknowledged, such as the University of Málaga, The Junta de Andalucía and the Government of Spain for continuous support of my research (CTQ2015-69391-P).

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  1. Department of Physical Chemistry, Faculty of Science, University of Málaga, Campus de Teatinos s/n, 29071, Málaga, Spain

    Juan Casado

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  1. Juan Casado
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Correspondence to Juan Casado.

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This article is part of the Topical Collection “Physical Organic Chemistry of Quinodimethanes”; edited by Yoshito Tobe, Takashi Kubo.

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Casado, J. Para-Quinodimethanes: A Unified Review of the Quinoidal-Versus-Aromatic Competition and its Implications. Top Curr Chem (Z) 375, 73 (2017). https://doi.org/10.1007/s41061-017-0163-2

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  • DOI: https://doi.org/10.1007/s41061-017-0163-2

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