Bay-aminated Octaazaperopyrenedioxides (OAPPDOs) as precursors for Diazepine and Diazepinone derivatives

• Verfasst von: Eichelmann, Robert [VerfasserIn]
• Verfasst von: Bender, Kai [VerfasserIn]
• Verfasst von: Günther, Julius A. [VerfasserIn]
• Verfasst von: Ziegenhagen, Levi A. [VerfasserIn]
• Verfasst von: Ballmann, Joachim [VerfasserIn]
• Verfasst von: Gade, Lutz H. [VerfasserIn]
• Titel: Bay-aminated Octaazaperopyrenedioxides (OAPPDOs) as precursors for Diazepine and Diazepinone derivatives
• Verf.angabe: Robert Eichelmann, Kai Bender, Julius A. Guenther, Levi A. Ziegenhagen, Joachim Ballmann, and Lutz H. Gade
• E-Jahr: 2025
• Jahr: January 31, 2025
• Umfang: 6 S.
• Fussnoten: Gesehen am 10.07.2025
• Titel Quelle: Enthalten in: Organic letters
• Ort Quelle: Washington, DC : ACS, 1999
• Jahr Quelle: 2025
• Band/Heft Quelle: 27(2025), 6, Seite 1396-1401
• ISSN Quelle: 1523-7052
• DOI: doi:10.1021/acs.orglett.4c04686
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1930257554

Abstract

Fully bay-aminated octaazaperopyrenedioxide (OAPPDO) derivatives have been accessible via Buchwald-Hartwig amination of the bay-chlorinated starting material. They were isolated as semiquinoidal species with a bent polycyclic core and characterized as nonfluorescent charge-transfer dyes. The corresponding secondary amines were synthesized by reduction and displayed typical absorption and emission behavior for perylene derivatives. One of the reduced amines served as a precursor for conversion of the secondary amino groups to 1,3-diazepine and -diazepinone units spanning the bay-area - seven-membered ring motifs hitherto unknown in perylene chemistry. The photophysical and electrochemical properties of the azaperylene dyes were investigated by absorption and emission spectroscopy supported by time-dependent density functional theory methods and cyclic voltammetry as well as differential pulse voltammetry.