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Synthesis and optical properties of Diaza- and Tetraazatetracenes

A series of functionalized diaza- and tetraazatetracenes was synthesized, either by condensation of an aromatic diamine with an ortho-quinone/diethyloxalate followed by chlorination with POCl3 to give diazatetracenes or by palladium-catalyzed coupling of a phenylenediamine with various 2,3-dichloroq...

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Main Authors: Lindner, Benjamin (Author) , Engelhart, Jens U. (Author) , Märken, Michaela (Author) , Tverskoy, Olena (Author) , Rominger, Frank (Author) , Enders, Markus (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: April 10, 2012
In: Chemistry - a European journal
Year: 2012, Volume: 18, Issue: 15, Pages: 4627-4633
ISSN:1521-3765
DOI:10.1002/chem.201103227
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/chem.201103227
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201103227
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Author Notes:Benjamin D. Lindner, Jens U. Engelhart, Michaela Märken, Olena Tverskoy, Anthony L. Appleton, Frank Rominger, Kenneth I. Hardcastle, Markus Enders, and Uwe H. F. Bunz
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Summary:A series of functionalized diaza- and tetraazatetracenes was synthesized, either by condensation of an aromatic diamine with an ortho-quinone/diethyloxalate followed by chlorination with POCl3 to give diazatetracenes or by palladium-catalyzed coupling of a phenylenediamine with various 2,3-dichloroquinoxalines to give tetraazatetracenes (after oxidation with MnO2). Representative examples included halogenated and nitrated derivatives. The optical properties of these azatetracenes were discussed with respect to their molecular structures and substitution patterns. The diazatetracenes and tetraazatetracenes formed two different groups that had significantly different electronic structures and properties. Furthermore, 1,2,3,4-tetrafluoro-6,11-bis((triisopropylsilyl)ethynyl)benzo[b]phenazine was synthesized, which is the first reported fluorinated diazatetracene. Single-crystal X-ray analysis of this compound is reported.
Item Description:Gesehen am 16.11.2018
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201103227

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