Robert Eichelmann, Kai Bender, Julius A Guenther, Levi A Ziegenhagen, Joachim Ballmann, Lutz H Gade
{"title":"<i>Bay</i>-Aminated Octaazaperopyrenedioxides (OAPPDOs) as Precursors for Diazepine and Diazepinone Derivatives.","authors":"Robert Eichelmann, Kai Bender, Julius A Guenther, Levi A Ziegenhagen, Joachim Ballmann, Lutz H Gade","doi":"10.1021/acs.orglett.4c04686","DOIUrl":null,"url":null,"abstract":"<p><p>Fully <i>bay</i>-aminated octaazaperopyrenedioxide (OAPPDO) derivatives have been accessible via Buchwald-Hartwig amination of the <i>bay</i>-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 <i>bay</i>-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.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1396-1401"},"PeriodicalIF":4.9000,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04686","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/30 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
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.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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