Synthesis of trifluoromethyl-substituted N-aryl-poly-1,2,3-triazole derivatives

Abstract

Synthesis, characterization, and physical properties of –CF₃ and –NO₂ substituted N-aryl-polytriazole derivatives are reported. The molecules are prepared by a reliable Cu-catalyzed [3 + 2]-cycloaddition between –CF₃ substituted aryl azides and alkynes followed by a nitration sequence and also the base-promoted nucleophilic displacement of the halo groups by the 1,2,3-triazoles. The compounds are characterized by analytical and spectroscopic methods; the solid state structures of some of the compounds are confirmed by X-ray diffraction techniques. The synthesized materials decompose in the range of 195–308 °C. Most of the –CF₃ and –NO₂ groups-bearing aryl triazoles exhibit good densities and acceptable detonation characteristics. Some of the fluorine containing polytriazole-bearing compounds showed positive heats of formation.