Polyazaacenes – On the Way to Stable, Fluorescent and Redox-Active Derivatives
作者： Frances Stöckner , Rainer Beckert , Dieter Gleich , Eckhard Birckner , Wolfgang Günther
关键词: Polymer chemistry 、 Xylene 、 Intramolecular force 、 Chemistry 、 Nucleophile 、 Redox 、 Fluorescence 、 Yield (chemistry) 、 Cascade reaction 、 Amine gas treating 、 Organic chemistry 、 Physical and Theoretical Chemistry
摘要: A new synthetic method for the preparation of polyazaacenes is described starting from two different nucleophilic building blocks. Disubstituted oxalic amidines 1 can be cyclized under mild conditions with 2,3-dichloro-5,6-dicyanopyrazine (3) to yield 5,6-dihydropyrazino[2,3-b]pyrazines 4a–c. By employing higher temperatures and 2 equiv. 3, octaazanaphthacene 6 isolated. Similarly, pyrazino[2,3-b]pyrazines bielectrophile 3 yielded novel dodecaazahexacenes 8 in addition semicyclized derivative 9. When tetraazafulvalene 10d was heated presence an amine xylene oxygen, octaazahexacene 13 isolated as main product. Instead 2, this highly fluorescent polyazaacene formed a cascade reaction which involves dyotropic rearrangement, intramolecular Diels–Alder multistep redox reaction. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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