Huisgen Rearrangement as a Strategic Tool for Trifluoromethyl‐Integrated Energetic Materials

A series of trifluoromethyl‐substituted energetic materials were synthesized by combining CC bonded 1,2,3‐triazoles with 1,3,4‐ and 1,2,4‐oxadiazoles through the Huisgen cycloaddition and other facile synthetic routes. All the novel compounds were fully characterized by multinuclear NMR, IR, TGA‐DSC, and elemental analysis. Compound 10 was confirmed by 15 N NMR spectroscopy, 6 and 11 were confirmed by single‐crystal XRD studies. Both compounds, 6 and 10, exhibit good densities (1.89 and 1.77 g cm −3 ), thermal stabilities (215 and 157°C), and are insensitive to mechanical stimuli (IS > 40 J, FS > 360 N). The solid‐state heat of formation was experimentally measured by an oxygen bomb calorimeter. Remarkably, compound 10 exhibits excellent detonation performance (VOD = 7308 m s −1 , DP = 22.15 GPa), estimated through the EXPLO 5 software, outperforming previously reported trifluoromethyl‐substituted energetic materials to the best of our knowledge. Overall, this work underscores a balanced design strategy and an effective synthetic route for tuning energetic properties, marking progress beyond traditional CHNO‐based frameworks.