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Alternating Covalent Bonding Interactions in a One-Dimensional Chain of a Phenalenyl-Based Singlet Biradical Molecule Having Kekulé Structures

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    Alternating Covalent Bonding Interactions in a One-Dimensional Chain of a Phenalenyl-Based Singlet Biradical Molecule Having Kekulé Structures
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    Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Institute for Molecular Science, Okazaki, Aichi 444-8585, Japan, Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan, and Department of Chemistry and Material Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan
    [email protected]
    †Graduate School of Science, Osaka University.
    ‡Institute for Molecular Science.
    §Graduate School of Engineering Science, Osaka University.
    ∥Osaka City University.
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    Cite this: J. Am. Chem. Soc. 2010, 132, 41, 14421–14428
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    https://doi.org/10.1021/ja1037287
    Published September 27, 2010
    Copyright © 2010 American Chemical Society
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    Abstract

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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 π−π 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 π-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 (1a). 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 Kekulé structure can be drawn for 2a.

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    Supporting Information

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    Crystal packing of 2a, HOMOs of α-spin and β-spin electrons for 2 calculated with a broken-symmetry UB3LYP method, input files for the Gaussian calculation, details of crystallographic data collection and structure refinement, tables of atomic coordinates, bond distances and angles, and isotropic thermal parameters in CIF format, and complete ref 31. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2010, 132, 41, 14421–14428
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