Protonation-Induced Cyclocondensation of 1-Aryl Ethynylanthraquinones: Expanding the π Conjugation

Authors

  • Mio Kondo,

    1. Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5841-8063
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  • Maai Uchikawa,

    1. Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5841-8063
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  • Wen-Wei Zhang Dr.,

    1. Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5841-8063
    2. Current address: State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
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  • Kosuke Namiki,

    1. Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5841-8063
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  • Shoko Kume Dr.,

    1. Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5841-8063
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  • Masaki Murata Dr.,

    1. Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5841-8063
    2. Current address: Fusion Domain Laboratory, Materials Laboratories, Sony Corporation, Atsugi Tec. No.2, 4-16-1 Okata Atsugi-shi, Kanagawa, 243-0021, Japan
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  • Yoshio Kobayashi Dr.,

    1. The Institute for Physical and Chemical Research (RIKEN), Hirosawa, Wako, Saitama, Japan
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  • Hiroshi Nishihara Prof.

    1. Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5841-8063
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  • This work was supported by Grants-in-Aid for Scientific Research (nos. 16047204 (area 434), 17205007, and 18655021), and CREST, Japan.

Abstract

original image

Ein Proton genügt: Die Cyclokondensation von 1-Arylethinylanthrachinonen in Gegenwart einer starken organischen Säure ergibt fast quantitativ die Oxodihydrodibenzochromenylium-Verbindungen (siehe z. B. das Ferrocenylderivat im Schema; blau C, rot O, violett Fe). Die Erweiterung des π-Systems führt zur Absenkung des π*-Orbitals und verstärkt den intramolekularen Elektronentransfer.

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