cAAC-Stabilized 9,10-diboraanthracenes-Acenes with Open-Shell Singlet Biradical Ground States.
acenes
biradicals
bond Activation
boron
heterocycles
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
19 Oct 2020
19 Oct 2020
Historique:
received:
09
06
2020
pubmed:
15
7
2020
medline:
15
7
2020
entrez:
15
7
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32662218
doi: 10.1002/anie.202008206
pmc: PMC7589216
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
19338-19343Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : GRK2112
Organisme : Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
ID : Foundation for a Capes-Humboldt postdoctoral fellowship
Organisme : Alexander von Humboldt-Stiftung
ID : Foundation for a Capes-Humboldt postdoctoral fellowship
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
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