Pentaarylazafullerenes and their Triaryldihydro and Tetraarylmonohydro Precursors

Authors

  • Regina Neubauer,

    1. Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
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  • Dr. Frank W. Heinemann,

    1. Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 1, 91058 Erlangen (Germany)
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  • Dr. Frank Hampel,

    1. Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
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  • Prof. Dr. Yves Rubin,

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East. Los Angeles, CA 90095 (USA)
    • Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East. Los Angeles, CA 90095 (USA)
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  • Prof. Dr. Andreas Hirsch

    Corresponding author
    1. Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
    • Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
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  • We thank the DFG (SFB 953) for financial support. The UCLA group thanks the National Science Foundation for grant CHE-1112569. R.N. is grateful to the Deutscher Akademischer Austauschdienst (DAAD) for an exchange fellowship at UCLA. We thank Dr. Alexandra Griffin (Agilent Technologies) for collecting X-ray data for 4 a (crystallized from toluene).

Abstract

original image

Give me five! The title compounds were isolated from the acid-catalyzed reaction of a C59N precursor with electron-rich aromatic compounds. Single-crystal X-ray diffraction on two compounds reveals characteristic packing motifs; the triaryldihydro derivative has a pseudo-stacked arrangement (C violet/yellow, N blue, O red, H white).

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