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

Please always quote using this URN: urn:nbn:de:bvb:20-opus-217795
  • 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 haveNarrow 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.show moreshow less

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Metadaten
Author: Christian Saalfrank, Felipe Fantuzzi, Thomas Kupfer, Benedikt Ritschel, Kai Hammond, Ivo Krummenacher, Rüdiger Bertermann, Raphael Wirthensohn, Maik Finze, Paul Schmid, Volker Engel, Bernd Engels, Holger BraunschweigORCiD
URN:urn:nbn:de:bvb:20-opus-217795
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Fakultät für Chemie und Pharmazie / Institut für Physikalische und Theoretische Chemie
Language:English
Parent Title (English):Angewandte Chemie International Edition
Year of Completion:2020
Volume:59
Issue:43
First Page:19338
Last Page:19343
Source:Angewandte Chemie International Edition 2020, 59(43):19338-19343. DOI: 10.1002/anie.202008206.
DOI:https://doi.org/10.1002/anie.202008206
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:acenes; biradicals; bond Activation; boron; heterocycles
Release Date:2021/07/20
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International