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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...

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Bibliographic Details
Main Authors: Martens-Kruck, Susanne (Author) , Hahn, Lena (Author) , Lombeck, Florian (Author) , Rybina, Arina (Author) , Wadepohl, Hubert (Author) , Gade, Lutz H. (Author)
Format: Article (Journal)
Language:English
Published: July 1, 2013
In: European journal of organic chemistry
Year: 2013, Volume: 2013, Issue: 24, Pages: 5295-5302
ISSN:1099-0690
DOI:10.1002/ejoc.201300662
Online Access: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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Author Notes:Susanne C. Martens, Lena Hahn, Florian Lombeck, Arina Rybina, Hubert Wadepohl, and Lutz H. Gade
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Summary: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.
Item Description:Gesehen am 23.06.2021
Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.201300662

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