Bay-aminated Octaazaperopyrenedioxides (OAPPDOs) as precursors for Diazepine and Diazepinone derivatives
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 corresp...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
January 31, 2025
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| In: |
Organic letters
Year: 2025, Volume: 27, Issue: 6, Pages: 1396-1401 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.4c04686 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.4c04686
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| Author Notes: | Robert Eichelmann, Kai Bender, Julius A. Guenther, Levi A. Ziegenhagen, Joachim Ballmann, and Lutz H. Gade |
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| 520 | |a 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. | ||
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