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Substituted tetraaza- and hexaazahexacenes and their N,N′-dihydro derivatives: syntheses, properties, and structures

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...

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Bibliographic Details
Main Authors: Engelhart, Jens U. (Author) , Lindner, Benjamin (Author) , Schaffroth, Manuel (Author) , Schrempp, David (Author) , Tverskoy, Olena (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: April 20, 2015
In: Chemistry - a European journal
Year: 2015, Volume: 21, Issue: 22, Pages: 8121-8129
ISSN:1521-3765
DOI:10.1002/chem.201500518
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201500518
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201500518
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Author Notes:Jens U. Engelhart, Benjamin D. Lindner, Manuel Schaffroth, David Schrempp, Olena Tverskoy, and Uwe H.F. Bunz
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Summary: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.
Item Description:Gesehen am 16.07.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201500518

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