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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2025-01-01
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| author | Yingchun Wang Thanh Chung Pham Jianjun Huang Junfeng Wu Wim Dehaen |
| author_facet | Yingchun Wang Thanh Chung Pham Jianjun Huang Junfeng Wu Wim Dehaen |
| author_sort | Yingchun Wang |
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| description | 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. |
| format | Article |
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| institution | Kabale University |
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| language | English |
| publishDate | 2025-01-01 |
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| series | Molecules |
| spelling | doaj-art-cf86fcc1d8604214b0726a0de0ee6a692025-01-10T13:19:03ZengMDPI AGMolecules1420-30492025-01-0130115610.3390/molecules30010156Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced EmissionYingchun Wang0Thanh Chung Pham1Jianjun Huang2Junfeng Wu3Wim Dehaen4Henan Key Laboratory of Water Pollution Control and Rehabilitation Technology, Henan University of Urban Construction, Pingdingshan 467036, ChinaSustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, BelgiumSustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, BelgiumHenan Key Laboratory of Water Pollution Control and Rehabilitation Technology, Henan University of Urban Construction, Pingdingshan 467036, ChinaSustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, BelgiumA 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.https://www.mdpi.com/1420-3049/30/1/156pyridine-fused triazapentalenemodified Suzuki cross-couplingCH arylationfluorescent propertiessolid-stateaggregated state |
| spellingShingle | Yingchun Wang Thanh Chung Pham Jianjun Huang Junfeng Wu Wim Dehaen Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission Molecules pyridine-fused triazapentalene modified Suzuki cross-coupling CH arylation fluorescent properties solid-state aggregated state |
| title | Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission |
| title_full | Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission |
| title_fullStr | Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission |
| title_full_unstemmed | Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission |
| title_short | Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission |
| title_sort | heteroaryl fused triazapentalenes synthesis and aggregation induced emission |
| topic | pyridine-fused triazapentalene modified Suzuki cross-coupling CH arylation fluorescent properties solid-state aggregated state |
| url | https://www.mdpi.com/1420-3049/30/1/156 |
| work_keys_str_mv | AT yingchunwang heteroarylfusedtriazapentalenessynthesisandaggregationinducedemission AT thanhchungpham heteroarylfusedtriazapentalenessynthesisandaggregationinducedemission AT jianjunhuang heteroarylfusedtriazapentalenessynthesisandaggregationinducedemission AT junfengwu heteroarylfusedtriazapentalenessynthesisandaggregationinducedemission AT wimdehaen heteroarylfusedtriazapentalenessynthesisandaggregationinducedemission |