Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission
A pyridine-fused triazapentalene shows weak fluorescence in solution and is readily accessible via nitrene-mediated cyclization. In this study, a modified Cadogan reaction was used to synthesize <b>HetATAP 1</b>. Palladium-catalyzed reactions have been used as post-functionalization meth...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-01-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/1/156 |
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| Summary: | A pyridine-fused triazapentalene shows weak fluorescence in solution and is readily accessible via nitrene-mediated cyclization. In this study, a modified Cadogan reaction was used to synthesize <b>HetATAP 1</b>. Palladium-catalyzed reactions have been used as post-functionalization methods. Interestingly, modified Suzuki cross-couplings with various boronic acids resulted in poor to moderate yields of <b>HetATAPs 2</b>–<b>5</b> which were arylated at the azole moiety. Direct CH arylation of <b>HetATAP 1</b> gave the products with the same regiochemistry in satisfactory yields. The structures of <b>HetATAPs 2</b>–<b>5</b> were confirmed using NMR analysis. In addition, the photophysical properties of <b>HetATAPs 1</b>–<b>5</b> were studied under various conditions. Particularly, the emission of <b>HetATAPs 2</b>–<b>5</b> is enhanced in the solid and aggregate state. |
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| ISSN: | 1420-3049 |