Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 41, Pages 14421-14428Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1037287
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Funding
- Yamada Science Foundation
- Ministry of Education, Culture, Sports, Science and Technology of Japan [2105, 18350007]
- JST
- CREST-JST
- Osaka University
- JSPS
- Grants-in-Aid for Scientific Research [18350007, 21106014, 22350018] Funding Source: KAKEN
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A novel naphthoquinoid singlet biradical (2a) stabilized by phenalenyl rings is prepared by a multistep procedure and is investigated in terms of covalent bonding interactions. The molecule 2a gives single crystals, in which a 1D chain is formed with a very short pi-pi contact at the overlapping phenalenyl rings. The unpaired electrons in 2a are involved in covalent bonding interactions not only within the molecule but also between the molecules in the 1D chain, and a linear conjugation is made of the alternating intra and intermolecular covalent bonding interactions through conventional pi-conjugation and multicenter bonding, respectively. The linear conjugation causes a lower-energy shift of the optical transition band in the crystal, but the transition energy is higher than that of the benzoquinoid singlet biradical (la). This optical behavior and the magnetic susceptibility measurements reveal that the intermolecular covalent bonding interaction in the 1D chain of 2a is greater in strength than the intramolecular one, despite the fact that a fully conjugated Kekule structure can be drawn for 2a.
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