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. © 2023 Wiley-VCH GmbH.