Substituted tetraaza- and hexaazahexacenes and their N,N′-dihydro derivatives

• Verfasst von: Engelhart, Jens U. [VerfasserIn]
• Verfasst von: Lindner, Benjamin [VerfasserIn]
• Verfasst von: Schaffroth, Manuel [VerfasserIn]
• Verfasst von: Schrempp, David [VerfasserIn]
• Verfasst von: Tverskoy, Olena [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: Substituted tetraaza- and hexaazahexacenes and their N,N′-dihydro derivatives
• Titelzusatz: syntheses, properties, and structures
• Verf.angabe: Jens U. Engelhart, Benjamin D. Lindner, Manuel Schaffroth, David Schrempp, Olena Tverskoy, and Uwe H.F. Bunz
• E-Jahr: 2015
• Jahr: April 20, 2015
• Umfang: 9 S.
• Fussnoten: Gesehen am 16.07.2020
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2015
• Band/Heft Quelle: 21(2015), 22, Seite 8121-8129
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201500518
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: amination
• Sach-SW: cross-coupling
• Sach-SW: heteroacenes
• Sach-SW: oxidation
• Sach-SW: palladium
• K10plus-PPN: 1724928805

Abstract

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.