Red Emissive Double Aza[7]helicenes with Antiaromaticity / Aromaticity Switching via the Redox-Induced Radical Cation and Dication Species.
Antiaromaticity
Aza[7]Helicene
Chirality
Radical Cation
Red Emission
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:
24 Apr 2023
24 Apr 2023
Historique:
received:
09
02
2023
medline:
7
3
2023
pubmed:
7
3
2023
entrez:
6
3
2023
Statut:
ppublish
Résumé
We herein present the synthetic approach to a new antiaromatic double aza[7]helicene C that features NN-embedded polycyclic aromatic hydrocarbons (PAHs). This heteroatom-doped helicene showed a rarely obtained long-wavelength emission and far-red circularly polarized luminescence (CPL) in the solid state. These optical and chiroptical properties could be ascribed to both the NN-PAH core structure and the further extension through angular ring fusions. Such a unique electronic structure also culminated in facile chemical oxidations of neutral C to the positively charged chiral radical (C⋅
Identifiants
pubmed: 36877097
doi: 10.1002/anie.202302019
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302019Subventions
Organisme : National Natural Science Foundation of China
ID : 22271013
Organisme : National Natural Science Foundation of China
ID : 21772012
Informations de copyright
© 2023 Wiley-VCH GmbH.
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The harmonic oscillator model of aromaticity (HOMA) calculated according to bond lengths was unsuccessful probably due to the distorted structure of the central N2C4 core (referring to the X-ray structure), and the optimal value Ropt used for the HOMA analysis may need to be further modified.
Deposition Numbers 2210533 (for 3), 2210534 (for 7), and 2210535 (for C) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.