Blue‐Emitting 2‐Fluoroaryl‐1, 2, 3‐Triazole Fluorophores: Synthesis, Theoretical Calculations, and Optical Properties. Issue 4 (6th March 2023)

• Record Type: Journal Article
• Authors: Lavrinchenko, Igor A.; Moseev, Timofey D.; Seleznev, Yuri A.; Varaksin, Mikhail V.; Tsmokaluk, Anton N.; Charushin, Valery N.; Chupakhin, Oleg N.
• Is Part Of: Asian journal of organic chemistry. Volume 12:Issue 4(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-03-06
• Subjects: azaheterocyclic N-oxides -- fluoroaromatics -- push-pull fluorophores -- Suzuki-Miyaura cross-coupling -- triazoles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202300008
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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 λ=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. Abstract : A convenient five‐step synthetic strategy affords novel push‐pull fluorophores based on N(2)‐fluoroaryl‐1, 2, 3‐triazoles to be of interest as functional blocks in the design of advanced blue‐emitting organic materials.