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Updated: Jun 3, 2025

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Heteroaryl-Fused Triazapentalenes: Synthesis and Aggregation-Induced Emission
Yingchun Wang1,2, Thanh Chung Pham2, Jianjun Huang2
1Henan Key Laboratory of Water Pollution Control and Rehabilitation Technology, Henan University of Urban Construction, Pingdingshan 467036, China.
Abstract:
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 HetATAP 1. 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 HetATAPs 2-5 which were arylated at the azole moiety. Direct CH arylation of HetATAP 1 gave the products with the same regiochemistry in satisfactory yields. The structures of HetATAPs 2-5 were confirmed using NMR analysis. In addition, the photophysical properties of HetATAPs 1-5 were studied under various conditions. Particularly, the emission of HetATAPs 2-5 is enhanced in the solid and aggregate state.
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