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| Verfasst von: | Heckershoff, Robin [VerfasserIn]  |
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| | Schnitzer, Tobias [VerfasserIn] |
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| | Diederich, Tim [VerfasserIn] |
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| | Eberle, Lukas [VerfasserIn] |
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| | Krämer, Petra [VerfasserIn] |
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| | Rominger, Frank [VerfasserIn] |
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| | Rudolph, Matthias [VerfasserIn] |
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| | Hashmi, A. Stephen K. [VerfasserIn] |
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| Titel: | Efficient synthesis of dipyrrolobenzenes and dipyrrolopyrazines via bidirectional gold catalysis |
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| Titelzusatz: | a combined synthetic and photophysical study |
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| Verf.angabe: | Robin Heckershoff, Tobias Schnitzer, Tim Diederich, Lukas Eberle, Petra Krämer, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi |
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| E-Jahr: | 2022 |
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| Jahr: | April 26, 2022 |
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| Umfang: | 11 S. |
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| Fussnoten: | Gesehen am 24.06.2022 |
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| Titel Quelle: | Enthalten in: American Chemical SocietyJournal of the American Chemical Society |
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| Ort Quelle: | Washington, DC : ACS Publications, 1879 |
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| Jahr Quelle: | 2022 |
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| Band/Heft Quelle: | 144(2022), 18, Seite 8306-8316 |
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| ISSN Quelle: | 1520-5126 |
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| Abstract: | 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. |
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| DOI: | doi:10.1021/jacs.2c02394 |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Volltext: https://doi.org/10.1021/jacs.2c02394 |
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| | DOI: https://doi.org/10.1021/jacs.2c02394 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| K10plus-PPN: | 1807735230 |
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| Verknüpfungen: | → Zeitschrift |
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Efficient synthesis of dipyrrolobenzenes and dipyrrolopyrazines via bidirectional gold catalysis / Heckershoff, Robin [VerfasserIn]; April 26, 2022 (Online-Ressource)
