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

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-Kekule polyc...

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Published inChemical science (Cambridge) Vol. 5; no. 5; pp. 1908 - 1914
Main Authors Li, Yuan, Huang, Kuo-Wei, Sun, Zhe, Webster, Richard D., Zeng, Zebing, Zeng, Wangdong, Chi, Chunyan, Furukawa, Ko, Wu, Jishan
Format Journal Article
LanguageEnglish
Published 01.01.2014
Subjects
Benzenoids
Blocking
Density functional theory
Displays
Hydrocarbons
Isomers
Mathematical analysis
Synthesis
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Summary: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-Kekule 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.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc53015a