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Cata-annulated azaacene bisimides

Ultra-electron-deficient azaacenes were synthesized via Buchwald-Hartwig coupling of ortho-diaminoarenes with chlorinated mellophanic diimide followed by oxidation of the intermediate N,N’-dihydro compounds with MnO2 or PbO2. The resulting cata-annulated bisimide azaacenes have ultrahigh electron af...

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Bibliographic Details
Main Authors: Elter, Maximilian (Author) , Ahrens, Lukas (Author) , Luo, Stella M. (Author) , Rominger, Frank (Author) , Freudenberg, Jan (Author) , Cao, Dennis D. (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: 2021
In: Chemistry - a European journal
Year: 2021, Volume: 27, Issue: 48, Pages: 12284-12288
ISSN:1521-3765
DOI:10.1002/chem.202101573
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202101573
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202101573
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Author Notes:Maximilian Elter, Lukas Ahrens, Stella M. Luo, Frank Rominger, Jan Freudenberg, Dennis D. Cao, and Uwe H.F. Bunz
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Summary:Ultra-electron-deficient azaacenes were synthesized via Buchwald-Hartwig coupling of ortho-diaminoarenes with chlorinated mellophanic diimide followed by oxidation of the intermediate N,N’-dihydro compounds with MnO2 or PbO2. The resulting cata-annulated bisimide azaacenes have ultrahigh electron affinities with first reduction potentials as low as −0.35 V recorded for a tetraazapentacene. Attempts to prepare a tetrakis(dicarboximide)tetraazaheptacene resulted in the formation of a symmetric butterfly dimer.
Item Description:Gesehen am 03.04.2023
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202101573

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