| |  Online-Ressource |
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| Verfasst von: | Martens, Susanne [VerfasserIn]  |
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| | Hahn, Lena [VerfasserIn] |
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| | Lombeck, Florian [VerfasserIn] |
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| | Rybina, Arina [VerfasserIn] |
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| | Wadepohl, Hubert [VerfasserIn] |
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| | Gade, Lutz H. [VerfasserIn] |
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| Titel: | Annulated heterocyclic derivatives of 1,3,6,8-tetraazapyrene |
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| Verf.angabe: | Susanne C. Martens, Lena Hahn, Florian Lombeck, Arina Rybina, Hubert Wadepohl, and Lutz H. Gade |
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| E-Jahr: | 2013 |
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| Jahr: | July 1, 2013 |
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| Umfang: | 8 S. |
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| Teil: | volume:2013 |
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| | year:2013 |
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| | number:24 |
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| | month:08 |
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| | pages:5295-5302 |
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| | extent:8 |
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| Fussnoten: | Gesehen am 23.06.2021 |
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| Titel Quelle: | Enthalten in: European journal of organic chemistry |
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| Ort Quelle: | Weinheim : Wiley-VCH Verl., 1998 |
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| Jahr Quelle: | 2013 |
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| Band/Heft Quelle: | 2013(2013), 24 vom: Aug., Seite 5295-5302 |
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| ISSN Quelle: | 1099-0690 |
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| Abstract: | Polyheterocyclic aromatic compounds combining the electron-poor 1,3,6,8-tetraazapyrene (TAPy) unit with electron-rich heterocycles are reported. They were obtained as side-products from the reaction of the tin “double salt” of tetraaminonaphthalene hydrochloride with trifluoroacetic anhydride in pyridine. Apart from the target product, 2,7-bis(trifluoromethyl)-1,3,6,8-tetraazapyrene (1), several novel heteroaromatics were obtained resulting from the annulation of a furan (2) or indolizine unit (3) to the TAPy core. Upon recrystallization from methanol, methanol added to compound 2 to yield the racemate of the homochiral diastereomer [(R,R)- and (S,S)-2a]. Compound 3 is strongly fluorescent (φ = 0.68 in toluene) and the emission spectra display a significant bathochromic shift with increasing solvent polarity. The HOMO of 3 is located on the indolizine part of the molecule, whereas the LUMO primarily resides on the tetraazapyrene unit, which suggests considerable intramolecular charge transfer in the corresponding π*←π transition. |
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| DOI: | doi:10.1002/ejoc.201300662 |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Volltext ; Verlag: https://doi.org/10.1002/ejoc.201300662 |
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| | Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201300662 |
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| | DOI: https://doi.org/10.1002/ejoc.201300662 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| Sach-SW: | Annulation |
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| | Fused ring sysntems |
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| | Heterocycles |
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| K10plus-PPN: | 1761138901 |
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| Verknüpfungen: | → Zeitschrift |
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Annulated heterocyclic derivatives of 1,3,6,8-tetraazapyrene / Martens, Susanne [VerfasserIn]; July 1, 2013 (Online-Ressource)
