Antiaromatic Hexaphyrins and Octaphyrins Stabilized by the Hydrogen-Bonding Interactions of meso-Imidazolyl Groups

Authors

  • Hirotaka Mori,

    1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
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  • Young Mo Sung,

    1. Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea), Fax: (+82) 2-364-7050
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  • Byung Sun Lee,

    1. Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea), Fax: (+82) 2-364-7050
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  • Prof. Dr. Dongho Kim,

    Corresponding author
    1. Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea), Fax: (+82) 2-364-7050
    • Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea), Fax: (+82) 2-364-7050
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  • Prof. Dr. Atsuhiro Osuka

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
    • Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-3970
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  • The work at Kyoto University was supported by Grants-in-Aid (no. 22245006 (A) and 20108001, “pi-Space”) from MEXT. The work at Yonsei University was supported by the World Class University Program (R32-2010-000-10217), the Mid-career Researcher Program (2010-0029668) of MEST, and an AFSOR/AOARD grant (FA2386-10-1-4080).

Abstract

original image

Stable antiaromatic expanded porphyrins were designed by the judicious implementation of meso-imidazolyl groups, which cause stabilization through the creation of a hydrogen-bonding network (see structures) that overcomes antiaromatic electronic destabilization. Both the [28]hexaphyrin 1 and the [36]octaphyrin 2, which contain imidazolyl groups at two opposite meso positions, are shown to be stable Hückel antiaromatic species.

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