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Issue 5, 2014
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A kinetically blocked 1,14:11,12-dibenzopentacene: a persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon

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Abstract

The synthesis of high-spin polycyclic hydrocarbons is very challenging due to their extremely high reactivity. Herein, we report the synthesis and characterization of a kinetically blocked 1,14:11,12-dibenzopentacene, DP-Mes, which represents a rare persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon. In contrast to its structural isomer 1,14:7,8-dibenzopentacene (heptazethrene) with a singlet biradical ground state, DP-Mes is a triplet diradical as confirmed by ESR and ESTN measurements and density functional theory calculations. DP-Mes also displays intermolecular antiferromagnetic spin interactions in solution at low temperature.

Graphical abstract: A kinetically blocked 1,14:11,12-dibenzopentacene: a persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon

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Publication details

The article was received on 31 Oct 2013, accepted on 30 Jan 2014 and first published on 30 Jan 2014


Article type: Edge Article
DOI: 10.1039/C3SC53015A
Citation: Chem. Sci., 2014,5, 1908-1914
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    A kinetically blocked 1,14:11,12-dibenzopentacene: a persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon

    Y. Li, K. Huang, Z. Sun, R. D. Webster, Z. Zeng, W. Zeng, C. Chi, K. Furukawa and J. Wu, Chem. Sci., 2014, 5, 1908
    DOI: 10.1039/C3SC53015A

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