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

作者：Sakamoto Ryota; Rao Koya Prabhakara; Nishihara Hiroshi^*

来源：Chemistry Letters, 2011, 40(12): 1316-1326.

DOI：10.1246/cl.2011.1316

In this account we describe ethynylene-conjugated arylethynyl-anthraquinone (ArAq) and bis(arylethynyl)anthraquinone (Ar(2)Aq) 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 pi-pi 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 pi-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.

• 出版日期2011-12-5