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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| Main Authors: | , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
April 26, 2022
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| In: |
Journal of the American Chemical Society
Year: 2022, Volume: 144, Issue: 18, Pages: 8306-8316 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/jacs.2c02394 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/jacs.2c02394 |
| Author Notes: | Robin Heckershoff, Tobias Schnitzer, Tim Diederich, Lukas Eberle, Petra Krämer, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi |
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| 520 | |a 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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