Hydrogen-Bonded Open-Shell Molecules: Synthesis and Physical Properties of the Oxophenalenoxyl-Based Radical with Hydroxyl Group

As a new precursor for a hydrogen-bonded open-shell system, we have designed and synthesized 2,5,8-tri- tert -butyl-4,9-dihydroxyphenalenone 1 from commercially available 2,7-dimethoxynaphthalene in nine steps. The neutral radical generated from 1 with active PbO 2 exhibits higher stability compared...

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Published inMolecular crystals and liquid crystals (Philadelphia, Pa. : 2003) Vol. 376; no. 1; pp. 543 - 548
Main Authors Maki, Suguru, Morita, Yasushi, Ohba, Tomohiro, Fukui, Kozo, Sato, Kazunobu, Shiomi, Daisuke, Takui, Takeji, Nakasuji, Kazuhiro
Format Journal Article
LanguageEnglish
Published Taylor & Francis Group 01.01.2002
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Summary:As a new precursor for a hydrogen-bonded open-shell system, we have designed and synthesized 2,5,8-tri- tert -butyl-4,9-dihydroxyphenalenone 1 from commercially available 2,7-dimethoxynaphthalene in nine steps. The neutral radical generated from 1 with active PbO 2 exhibits higher stability compared with other 6-oxophenalenoxyl derivatives in the solid state. From the results of ESR and ENDOR/TRIPLE spectroscopies and MO calculations, the structure of the radical is identified to be monoradical 2 with a hydroxyl group.
ISSN:1542-1406
1563-5287
DOI:10.1080/713738424