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    Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals

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    Type
    Article
    Authors
    Zeng, Zebing
    Shi, Xueliang
    Chi, Chunyan
    López Navarrete, Juan T.
    Casado, Juan
    Wu, Jishan
    Date
    2015
    Permanent link to this record
    http://hdl.handle.net/10754/599405
    
    Metadata
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    Abstract
    © 2015 The Royal Society of Chemistry. 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.
    Citation
    Zeng Z, Shi X, Chi C, López Navarrete JT, Casado J, et al. (2015) Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals. Chem Soc Rev 44: 6578–6596. Available: http://dx.doi.org/10.1039/c5cs00051c.
    Sponsors
    The work at Singapore was financially supported by AcRF MOE Tier 2 grants (MOE2014-T2-1-080), Tier 3 grant (MOE2014-T3-1-004) and A*STAR JCO grant (1431AFG100). J.C. and J.T.L.N. acknowledge financial support from MINECO of Spain (CTQ2012-33733). We also would like to say special thanks to other major collaborators, Professor D. H. Kim in Yonsei University, Professor J. Ding in NUS, Professor K. Huang in KAUST, Professor K. Furukawa from Niigata University and Professor R. Webster in NTU for their valuable contributions.
    Publisher
    Royal Society of Chemistry (RSC)
    Journal
    Chemical Society Reviews
    DOI
    10.1039/c5cs00051c
    PubMed ID
    25994857
    ae974a485f413a2113503eed53cd6c53
    10.1039/c5cs00051c
    Scopus Count
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