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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...
Autores principales: | , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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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. |
format | Online Article Text |
id | pubmed-7589216 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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