Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
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Arylethynylanthraquinone and Bis(arylethynyl)anthraquinone: Strong Donor–Acceptor Interaction and Proton-induced Cyclization to Form Pyrylium and Dipyrylium Salts
Ryota SakamotoKoya Prabhakara RaoHiroshi Nishihara
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2011 Volume 40 Issue 12 Pages 1316-1326


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.

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© 2011 The Chemical Society of Japan
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