4.5 Article

Blue-Emitting 2-Fluoroaryl-1,2,3-Triazole Fluorophores: Synthesis, Theoretical Calculations, and Optical Properties

期刊

ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 12, 期 4, 页码 -

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202300008

关键词

azaheterocyclic N-oxides; fluoroaromatics; push-pull fluorophores; Suzuki-Miyaura cross-coupling; triazoles

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A convenient multistep synthetic method was reported to design push-pull fluorophores based on the N(2)-fluoroaryl-1,2,3-triazole scaffold for blue-emitting organic materials. The synthetic strategy involved five steps with yields ranging from 60% to 99% at each stage. The obtained photoactive molecules showed blue-violet emission with a quantum yield of >99% in solvents of different polarities. The electron transfer mechanism in the excited states was also studied using DFT and CIS calculations.
A convenient multistep synthetic methodology to afford prospective push-pull fluorophores based on the N(2)-fluoroaryl-1,2,3-triazole scaffold as valuable functional blocks in the design of blue-emitting organic materials is reported. The strategy includes five synthetic steps with yields of 60-99% at each stage. The obtained photoactive molecules, 2-fluoroaryl-5-aryl-4-methyl-1,2,3-triazoles, were found to possess a blue-violet emission in the range of lambda=330-440 nm and the absolute quantum yield of >99% in solvents of different polarities. The electron transfer mechanistic features in the excited states for the developed N(2)-fluoroaryl-1,2,3-triazoles compared to the 1,2,3-triazoles-1-oxide analogues were also studied by using DFT and CIS calculations.

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