Arylethynylanthraquinone and Bis(arylethynyl)anthraquinone: Strong Donor–Acceptor Interaction and Proton-induced Cyclization to Form Pyrylium and Dipyrylium Salts

• Ryota Sakamoto

  Department of Chemistry, Graduate School of Science, The University of Tokyo

• Koya Prabhakara Rao

  Department of Chemistry, Graduate School of Science, The University of Tokyo

• Hiroshi Nishihara

  Department of Chemistry, Graduate School of Science, The University of Tokyo

抄録

In this account we describe ethynylene-conjugated arylethynylanthraquinone (ArAq) and bis(arylethynyl)anthraquinone (Ar2Aq) which possess ferrocene, triarylamine, platinadithiolene complex, p-methoxybenzene, p-methylbenzene, m-methylbenzene, and benzene as electron-donating arenes (Ar), and anthraquinone (Aq) as an electron acceptor. This series of compounds features donor–acceptor (D–A) interactions: (1) Expression of intramolecular charge-transfer (ICT) transitions; (2) flexible single crystal networks constructed by intermolecular D–A π–π stacking, which undergo guest-induced reversible crystal-to-crystal transformations. In addition, ArAq and Ar2Aq experience proton-induced cyclization so as to produce pyrylium and dipyrylium salts. These salts feature further expanded π-conjugation and stronger D–A interaction: (1) More red-shifted ICT transitions and narrower HOMO–LUMO gaps; (2) bright fluorescence; (3) valence tautomerism (VT); (4) unique reactivities.

収録刊行物

• Chemistry Letters

  Chemistry Letters 40 (12), 1316-1326, 2011-11-26

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360283694088214912
• NII論文ID: 130004426130
• DOI: 10.1246/cl.2011.1316
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/40/12/1316/55606207/cl.2011.1316.pdf
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