Protonation-induced Cyclization of 1,8-Bis(arylethynyl)anthraquinones : Monopyrylium Salt Formation and Intensification of Donor-Acceptor Interaction

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著者

    • KONDO Mio
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • SAKAMOTO Ryota
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • KUSAMOTO Tetsuro
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • KUME Shoko
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • NISHIHARA Hiroshi
    • Department of Chemistry, Graduate School of Science, The University of Tokyo

抄録

We previously reported protonation-induced double cyclization reaction of <b>1,4-Ar<sub>2</sub>Aq</b> and <b>1,5-Ar<sub>2</sub>Aq</b> (<b>Ar<sub>2</sub>Aq</b>: bis(arylethynyl)anthraquinone) with strong acid HX that generated the corresponding dipyrylium salts <b>[1,4-Ar<sub>2</sub>Pyl<sub>2</sub>]X<sub>2</sub></b> and <b>[1,5-Ar<sub>2</sub>Pyl<sub>2</sub>]X<sub>2</sub></b>. In this communication we disclose the protonation reactions of <b>1,8-Fc<sub>2</sub>Aq</b> (<b>Fc</b>: ferrocenyl), <b>1,8-Am<sub>2</sub>Aq</b> (<b>Am</b>: 4-<i>N</i>,<i>N</i>-bis(4-methoxyphenyl)aminophenyl), and <b>1,8-AmFcAq</b>, which is the first example of heterodonor molecules in the <b>Ar<sub>2</sub>Aq</b> series, and synthesized by means of stepwise Sonogashira–Hagihara cross-coupling reactions. In contrast to the <b>1,4-Ar<sub>2</sub>Aq</b> and <b>1,5-Ar<sub>2</sub>Aq</b> series, <b>1,8-Ar<sub>2</sub>Aq</b> undergoes protonation-induced single cyclization, so that it is converted into the corresponding monopyrylium salt <b>[1,8-Ar<sub>2</sub>Pyl]X</b>. <b>[1,8-Ar<sub>2</sub>Pyl]X</b> features an extremely small HOMO–LUMO gap (0.50–0.73 V), ascribable to the significant lowering of the LUMO level upon the pyrylium formation.

収録刊行物

  • Chemistry letters

    Chemistry letters 40(12), 1456-1458, 2011-12-05

    公益社団法人 日本化学会

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各種コード

  • NII論文ID(NAID)
    10030221899
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    SHO
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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