Borocyclic Radicals Prepared from Orthoquinone-Containing Polycyclic Aromatics by Photoirradiation

Borocyclic radicals with highly conjugated aromatics were generated from orthoquinone-containing polycyclic aromatic compounds by trapping the photoinduced triplet state with simple boron halide under irradiation with light of appropriate wavelength. The picene-based borocyclic radical was remarkabl...

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Published inJournal of organic chemistry Vol. 87; no. 5; pp. 3647 - 3651
Main Authors Urakawa, Kazuki, Yatsuoka, Yurie, Kawabata, Yuta, Masu, Hyuma, Matsuda, Masaki, Ishikawa, Hayato
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.03.2022
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Summary:Borocyclic radicals with highly conjugated aromatics were generated from orthoquinone-containing polycyclic aromatic compounds by trapping the photoinduced triplet state with simple boron halide under irradiation with light of appropriate wavelength. The picene-based borocyclic radical was remarkably stable when stored at 23 °C in a desiccator for over 1 year. The crystal structure of this stable radical had a stacking structure of a planar π-conjugated system, and the electrical conductivity was higher than those of ordinary organic radical systems.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02283