Annulated heterocyclic derivatives of 1,3,6,8-tetraazapyrene
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 pyr...
Gespeichert in:
| Hauptverfasser: | , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
July 1, 2013
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| In: |
European journal of organic chemistry
Year: 2013, Jahrgang: 2013, Heft: 24, Pages: 5295-5302 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201300662 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.201300662 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201300662 
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| Verfasserangaben: | Susanne C. Martens, Lena Hahn, Florian Lombeck, Arina Rybina, Hubert Wadepohl, and Lutz H. Gade |
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| 245 | 1 | 0 | |a Annulated heterocyclic derivatives of 1,3,6,8-tetraazapyrene |c Susanne C. Martens, Lena Hahn, Florian Lombeck, Arina Rybina, Hubert Wadepohl, and Lutz H. Gade |
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| 520 | |a 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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