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cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States

Narrow HOMO–LUMO gaps and high charge‐carrier mobilities make larger acenes potentially high‐efficient materials for organic electronic applications. The performance of such molecules was shown to significantly increase with increasing number of fused benzene rings. Bulk quantities, however, can onl...

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Autores principales: Saalfrank, Christian, Fantuzzi, Felipe, Kupfer, Thomas, Ritschel, Benedikt, Hammond, Kai, Krummenacher, Ivo, Bertermann, Rüdiger, Wirthensohn, Raphael, Finze, Maik, Schmid, Paul, Engel, Volker, Engels, Bernd, Braunschweig, Holger
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7589216/
https://www.ncbi.nlm.nih.gov/pubmed/32662218
http://dx.doi.org/10.1002/anie.202008206
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author Saalfrank, Christian
Fantuzzi, Felipe
Kupfer, Thomas
Ritschel, Benedikt
Hammond, Kai
Krummenacher, Ivo
Bertermann, Rüdiger
Wirthensohn, Raphael
Finze, Maik
Schmid, Paul
Engel, Volker
Engels, Bernd
Braunschweig, Holger
author_facet Saalfrank, Christian
Fantuzzi, Felipe
Kupfer, Thomas
Ritschel, Benedikt
Hammond, Kai
Krummenacher, Ivo
Bertermann, Rüdiger
Wirthensohn, Raphael
Finze, Maik
Schmid, Paul
Engel, Volker
Engels, Bernd
Braunschweig, Holger
author_sort Saalfrank, Christian
collection PubMed
description Narrow HOMO–LUMO gaps and high charge‐carrier mobilities make larger acenes potentially high‐efficient materials for organic electronic applications. The performance of such molecules was shown to significantly increase with increasing number of fused benzene rings. Bulk quantities, however, can only be obtained reliably for acenes up to heptacene. Theoretically, (oligo)acenes and (poly)acenes are predicted to have open‐shell singlet biradical and polyradical ground states, respectively, for which experimental evidence is still scarce. We have now been able to dramatically lower the HOMO–LUMO gap of acenes without the necessity of unfavorable elongation of their conjugated π system, by incorporating two boron atoms into the anthracene skeleton. Stabilizing the boron centers with cyclic (alkyl)(amino)carbenes gives neutral 9,10‐diboraanthracenes, which are shown to feature disjointed, open‐shell singlet biradical ground states.
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spelling pubmed-75892162020-10-30 cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States Saalfrank, Christian Fantuzzi, Felipe Kupfer, Thomas Ritschel, Benedikt Hammond, Kai Krummenacher, Ivo Bertermann, Rüdiger Wirthensohn, Raphael Finze, Maik Schmid, Paul Engel, Volker Engels, Bernd Braunschweig, Holger Angew Chem Int Ed Engl Research Articles Narrow HOMO–LUMO gaps and high charge‐carrier mobilities make larger acenes potentially high‐efficient materials for organic electronic applications. The performance of such molecules was shown to significantly increase with increasing number of fused benzene rings. Bulk quantities, however, can only be obtained reliably for acenes up to heptacene. Theoretically, (oligo)acenes and (poly)acenes are predicted to have open‐shell singlet biradical and polyradical ground states, respectively, for which experimental evidence is still scarce. We have now been able to dramatically lower the HOMO–LUMO gap of acenes without the necessity of unfavorable elongation of their conjugated π system, by incorporating two boron atoms into the anthracene skeleton. Stabilizing the boron centers with cyclic (alkyl)(amino)carbenes gives neutral 9,10‐diboraanthracenes, which are shown to feature disjointed, open‐shell singlet biradical ground states. John Wiley and Sons Inc. 2020-08-25 2020-10-19 /pmc/articles/PMC7589216/ /pubmed/32662218 http://dx.doi.org/10.1002/anie.202008206 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Saalfrank, Christian
Fantuzzi, Felipe
Kupfer, Thomas
Ritschel, Benedikt
Hammond, Kai
Krummenacher, Ivo
Bertermann, Rüdiger
Wirthensohn, Raphael
Finze, Maik
Schmid, Paul
Engel, Volker
Engels, Bernd
Braunschweig, Holger
cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States
title cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States
title_full cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States
title_fullStr cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States
title_full_unstemmed cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States
title_short cAAC‐Stabilized 9,10‐diboraanthracenes—Acenes with Open‐Shell Singlet Biradical Ground States
title_sort caac‐stabilized 9,10‐diboraanthracenes—acenes with open‐shell singlet biradical ground states
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7589216/
https://www.ncbi.nlm.nih.gov/pubmed/32662218
http://dx.doi.org/10.1002/anie.202008206
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