Access to Functionalized Pyrenes, Peropyrenes, Terropyrenes, and Quarterropyrenes via Reductive Aromatization.
crystallography
cyclovoltammetry
fluorescence
organic dyes
reductive aromatization
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:
07 Jun 2021
07 Jun 2021
Historique:
revised:
11
03
2021
received:
15
01
2021
pubmed:
17
3
2021
medline:
17
3
2021
entrez:
16
3
2021
Statut:
ppublish
Résumé
Herein we report a versatile concept for the synthesis of fourfold functionalized, soluble pyrenes, peropyrenes, terropyrenes, and quarterropyrenes. They were obtained by a modular stepwise approach towards the rylene scaffold via Suzuki-Miyaura cross coupling, oxidative cyclodehydrogenation in the presence of caesium hydroxide under air, and finally zinc-mediated reductive silylation. The silylated reaction products were characterized by X-ray crystallography. The first example of a synthesized and crystallized quarterropyrene is presented and its oxidation reaction investigated. The functionalized ropyrenes were systematically characterized by means of UV/Vis-NIR and photoluminescence spectroscopy showing a bathochromic shift of 80 nm per naphthalene unit and a nearly linear increase of the extinction coefficients. Cyclic voltammograms and DFT calculations identify them as electron-rich dyes and show a narrowing of the electrochemically determined HOMO-LUMO gap and lower oxidation potentials for the higher homologues.
Identifiants
pubmed: 33724640
doi: 10.1002/anie.202100686
pmc: PMC8252597
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13631-13635Subventions
Organisme : Hessisches Ministerium für Wissenschaft und Kunst
ID : PriOSS
Informations de copyright
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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