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Jahn–Teller Effect in Circulenes: X-ray Diffraction Study of Coronene and Corannulene Radical Anions

Authors

  • Dr. Alexander S. Filatov,

    1. Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222 (USA), Fax: (+1) 518-442-3462
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  • Natalie J. Sumner,

    1. Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222 (USA), Fax: (+1) 518-442-3462
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  • Sarah N. Spisak,

    1. Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222 (USA), Fax: (+1) 518-442-3462
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  • Dr. Alexander V. Zabula,

    1. Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222 (USA), Fax: (+1) 518-442-3462
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  • Andrey Yu. Rogachev,

    1. Baker Laboratory, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853 (USA)
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  • Prof. Marina A. Petrukhina

    Corresponding author
    1. Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222 (USA), Fax: (+1) 518-442-3462
    • Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222 (USA), Fax: (+1) 518-442-3462
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Abstract

Single-crystal X-ray diffraction studies of two polyaromatic radical anions crystallized as sodium salts, namely [Na(DME)3]+[C20H10] (1) and [Na(DME)3]+[C24H12] (2) are reported. This allowed the first structural evaluation of Jahn–Teller (JT) effects for monoreduced circulenes and a comparison between bowl-shaped corannulene and planar coronene. The Cs and D2h symmetrical distortions are found to fit the experimental data for C20H10.− and C24H12.−, respectively. The continuous symmetry measure (CSM) analysis was carried out to provide a quantitative measure of the JT distortions in 1 and 2. In addition, the X-ray crystallographic results were fully supported by DFT calculations.

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