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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, and others. (2020) cAAC-Stabilized 9,10-diboraanthracenes—Acenes with Open-Shell Singlet Biradical Ground States. Angewandte Chemie International Edition, 59 (43). pp. 19338-19343. ISSN 1433-7851. (doi:10.1002/anie.202008206) (KAR id:98537)

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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.

Item Type: Article
DOI/Identification number: 10.1002/anie.202008206
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Funders: Deutsche Forschungsgemeinschaft (
Coordenação de Aperfeicoamento de Pessoal de Nível Superior (
Alexander von Humboldt Foundation (
Depositing User: Felipe Fantuzzi
Date Deposited: 30 Nov 2022 15:52 UTC
Last Modified: 06 Dec 2022 14:50 UTC
Resource URI: (The current URI for this page, for reference purposes)
Fantuzzi, Felipe:
Kupfer, Thomas:
Krummenacher, Ivo:
Finze, Maik:
Engel, Volker:
Engels, Bernd:
Braunschweig, Holger:
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