Synthesis of Triptycene-Substituted Azapentacene and Azahexacene Derivatives

• Verfasst von: Biegger, Philipp [VerfasserIn]
• Verfasst von: Tverskoy, Olena [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: Synthesis of Triptycene-Substituted Azapentacene and Azahexacene Derivatives
• Verf.angabe: Philipp Biegger, Olena Tverskoy, Frank Rominger, and Uwe H. F. Bunz
• E-Jahr: 2016
• Jahr: 28 September 2016
• Umfang: 8 S.
• Fussnoten: Gesehen am 11.05.2020
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2016
• Band/Heft Quelle: 22(2016), 45, Seite 16315-16322
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201603360
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: azaacenes
• Sach-SW: condensation reactions
• Sach-SW: cyclobutadiene
• Sach-SW: homogeneous catalysis
• Sach-SW: triptycene
• K10plus-PPN: 1697823149

Abstract

Abstract We describe the synthesis and characterization of novel iptycene-substituted azaacenes by using either a classic condensation route (diamine plus ortho-quinone) and/or a Pd-catalyzed coupling of an aromatic diamine with an aromatic dihalide. The attachment of an iptycene unit leads to a significant blueshift (15?nm) in the UV/Vis spectra of these azaacenes. The iptycene unit stabilizes a hexaazahexacene with a ?max?abs of 833?nm. By employing 5,6-diamino(benzothiadiazole) as a synthon for tetraaminobenzene, we could prepare the symmetrical bis-triptycene-substituted tetraazapentacene in high yields.