5,11-Diazadibenzo[hi,qr]tetracene: Synthesis, Properties, and Reactivity toward Nucleophilic Reagents.
NIR-absorption
heteroacenes
oxidative nucleophilic substitution of hydrogen
polycyclic heteroaromatics
redox activity
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
21 Jun 2021
21 Jun 2021
Historique:
received:
03
03
2021
pubmed:
15
4
2021
medline:
15
4
2021
entrez:
14
4
2021
Statut:
ppublish
Résumé
5,11-Diazadibenzo[hi,qr]tetracene was synthesized as a new nitrogen-substituted polycyclic heteroaromatic compound by Pd-catalyzed cycloisomerization of an alkyne precursor followed by oxidative cyclization with bis(trifluoroacetoxy)iodobenzene. The substitution of imine-type nitrogen atoms significantly enhanced its electron-accepting character and facilitated the direct nucleophilic addition of arylamines under strongly basic conditions to afford the desired amino-substituted products. The introduction of amino groups induced a remarkable red-shift in their absorption spectra; the tetrasubstituted product exhibited intense near-infrared absorbing property. Furthermore, the π-electronic system, which includes a redox-active 1,4-diazabutadiene moiety, underwent reversible interconversion to its corresponding reduced form upon reduction with NaBH
Identifiants
pubmed: 33851483
doi: 10.1002/chem.202100944
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
8951-8955Subventions
Organisme : Japan Society for the Promotion of Science
ID : 19K15536
Informations de copyright
© 2021 Wiley-VCH GmbH.
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