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 MnO(2) or PbO(2). The resulting cata‐annulated bisimide azaacenes have ultrahigh electro...

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Detalles Bibliográficos
Autores principales: Elter, Maximilian, Ahrens, Lukas, Luo, Stella M., Rominger, Frank, Freudenberg, Jan, Cao, Dennis D., Bunz, Uwe H. F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457205/
https://www.ncbi.nlm.nih.gov/pubmed/34196059
http://dx.doi.org/10.1002/chem.202101573
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author Elter, Maximilian
Ahrens, Lukas
Luo, Stella M.
Rominger, Frank
Freudenberg, Jan
Cao, Dennis D.
Bunz, Uwe H. F.
author_facet Elter, Maximilian
Ahrens, Lukas
Luo, Stella M.
Rominger, Frank
Freudenberg, Jan
Cao, Dennis D.
Bunz, Uwe H. F.
author_sort Elter, Maximilian
collection PubMed
description 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 MnO(2) or PbO(2). 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.
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spelling pubmed-84572052021-09-28 Cata‐Annulated Azaacene Bisimides Elter, Maximilian Ahrens, Lukas Luo, Stella M. Rominger, Frank Freudenberg, Jan Cao, Dennis D. Bunz, Uwe H. F. Chemistry Communications 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 MnO(2) or PbO(2). 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. John Wiley and Sons Inc. 2021-07-29 2021-08-25 /pmc/articles/PMC8457205/ /pubmed/34196059 http://dx.doi.org/10.1002/chem.202101573 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Elter, Maximilian
Ahrens, Lukas
Luo, Stella M.
Rominger, Frank
Freudenberg, Jan
Cao, Dennis D.
Bunz, Uwe H. F.
Cata‐Annulated Azaacene Bisimides
title Cata‐Annulated Azaacene Bisimides
title_full Cata‐Annulated Azaacene Bisimides
title_fullStr Cata‐Annulated Azaacene Bisimides
title_full_unstemmed Cata‐Annulated Azaacene Bisimides
title_short Cata‐Annulated Azaacene Bisimides
title_sort cata‐annulated azaacene bisimides
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457205/
https://www.ncbi.nlm.nih.gov/pubmed/34196059
http://dx.doi.org/10.1002/chem.202101573
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