Substituted Tetraaza‐ and Hexaazahexacenes and their N, N′‐Dihydro Derivatives: Syntheses, Properties, and Structures. Issue 22 (20th April 2015)

• Record Type: Journal Article
• Authors: Engelhart, Jens U.; Lindner, Benjamin D.; Schaffroth, Manuel; Schrempp, David; Tverskoy, Olena; Bunz, Uwe H. F.
• Is Part Of: Chemistry. Volume 21:Issue 22(2015)
• Page Start: 8121
• Page End: 8129
• Publication Date: 2015-04-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201500518
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The palladium‐catalyzed coupling of a substituted <italic>o</italic>‐diaminoanthracene and a substituted <italic>o</italic>‐diaminophenazine to substituted 2, 3‐dichloroquinoxalines furnishes 10 differently substituted <italic>N</italic>, <italic>N</italic>′‐dihydrotetraaza‐ or ‐hexaazahexacenes with the quinoxaline group of the azaacenes carrying fluorine, chlorine, or nitro groups. The <italic>N</italic>, <italic>N</italic>′‐dihydrotetraazahexacenes with hydrogen, chlorine, and fluorine subtituents are oxidized to azaacenes, whereas only the parent <italic>N</italic>, <italic>N</italic>′‐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 <italic>N</italic>, <italic>N</italic>′‐dihydrohexaazahexacene have also been structurally characterized.</p> </abstract>