A stable bis(benzocyclobutadiene)-annelated tetraazapentacene derivative

• Verfasst von: Biegger, Philipp [VerfasserIn]
• Verfasst von: Schaffroth, Manuel [VerfasserIn]
• Verfasst von: Tverskoy, Olena [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: A stable bis(benzocyclobutadiene)-annelated tetraazapentacene derivative
• Verf.angabe: Philipp Biegger, Manuel Schaffroth, Olena Tverskoy, Frank Rominger, and Uwe H. F. Bunz
• E-Jahr: 2016
• Jahr: 15 September 2016
• Umfang: 6 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), 44, Seite 15896-15901
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201602675
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: aromaticity
• Sach-SW: azaheteropolycycle
• Sach-SW: condensation
• Sach-SW: cyclobutadiene
• Sach-SW: tetraazapentacene
• K10plus-PPN: 1697822029

Abstract

Abstract Biphenylene-2,3-dione is a powerful reagent to build up cyclobutadiene-containing azapolyheterocycles. The target structures are formed in high yields through classical condensation of suitable aromatic diamines with the biphenylenedione. To achieve the title compound, the biphenylenedione is coupled with a diaminobenzothiadiazole derivative. Reductive cleavage of the thiadiazole ring and subsequent condensation with the biphenylenedione gives the title compound in which a central tetraazapentacene is flanked by two benzocyclobutadiene units. This compound is stable despite its extended π-system and its optical features are blueshifted in comparison to those of the symmetrical tetraazapentacene.