Substituted Tetraaza- and Hexaazahexacenes and theirN,N′-Dihydro Derivatives: Syntheses, Properties, and Structures

Autor: David Fridolin Schrempp, Benjamin D. Lindner, Olena Tverskoy, Uwe H. F. Bunz, Manuel Schaffroth, Jens U. Engelhart
Rok vydání: 2015
Předmět:
Zdroj: Chemistry - A European Journal. 21:8121-8129
ISSN: 0947-6539
DOI: 10.1002/chem.201500518
Popis: The palladium-catalyzed coupling of a substituted o-diaminoanthracene and a substituted o-diaminophenazine to substituted 2,3-dichloroquinoxalines furnishes 10 differently substituted N,N'-dihydrotetraaza- or -hexaazahexacenes with the quinoxaline group of the azaacenes carrying fluorine, chlorine, or nitro groups. The N,N'-dihydrotetraazahexacenes with hydrogen, chlorine, and fluorine subtituents are oxidized to azaacenes, whereas only the parent N,N'-dihydrohexaazahexacenes, with hydrogen substituents, are oxidized by MnO2. The resultant azaacenes are characterized by their optical and spectroscopic data. In addition, single-crystal X-ray structures have been obtained for the parent tetraazahexacenes and their difluoro-substituted derivatives. The di- and tetrachloro derivatives of the N,N'-dihydrohexaazahexacene have also been structurally characterized.
Databáze: OpenAIRE
Nepřihlášeným uživatelům se plný text nezobrazuje