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Efficient synthesis of dipyrrolobenzenes and dipyrrolopyrazines via bidirectional gold catalysis: a combined synthetic and photophysical study

New N-heterocyclic fluorophores are sought-after compounds for organic electronic devices. Here, we report on a straightforward synthesis to access meta/para-dipyrrolobenzenes and para-dipyrrolopyrazines in high yields using a bidirectional gold-catalyzed cyclization strategy. The versatility of our...

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Hauptverfasser: Heckershoff, Robin (VerfasserIn) , Schnitzer, Tobias (VerfasserIn) , Diederich, Tim (VerfasserIn) , Eberle, Lukas (VerfasserIn) , Krämer, Petra (VerfasserIn) , Rominger, Frank (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: April 26, 2022
In: Journal of the American Chemical Society
Year: 2022, Jahrgang: 144, Heft: 18, Pages: 8306-8316
ISSN:1520-5126
DOI:10.1021/jacs.2c02394
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/jacs.2c02394
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Verfasserangaben:Robin Heckershoff, Tobias Schnitzer, Tim Diederich, Lukas Eberle, Petra Krämer, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:New N-heterocyclic fluorophores are sought-after compounds for organic electronic devices. Here, we report on a straightforward synthesis to access meta/para-dipyrrolobenzenes and para-dipyrrolopyrazines in high yields using a bidirectional gold-catalyzed cyclization strategy. The versatility of our reaction protocol was showcased by preparing dipyrroloarenes with different substituents, various functional groups, and in a multitude of substitution patterns. Furthermore, we showed that the dipyrroloarenes can be post-modified by N-alkylation to improve the solubility or bromination to yield precursors for further derivatization via cross-coupling. Investigation of the photophysical properties of the─mostly unprecedented─dipyrroloarenes identified strong blue emitters such as the diphenyl meta-dipyrrolobenzene with a quantum yield of 98%. Moreover, we showed that changes in the solvent polarity or interactions with Lewis acids such as borane can be used to fine-tune the photophysical properties of the fluorophores.
Beschreibung:Gesehen am 24.06.2022
Beschreibung:Online Resource
ISSN:1520-5126
DOI:10.1021/jacs.2c02394

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