Fully C-Nitrated Tricyclic Azoles: A Good Balance between High Energy and Low Sensitivity

Presently, the central requirement of novel high-energy material research involves the harmonization of detonation performance and mechanical sensitivity. In this work, two advanced high-energy insensitive tricyclic energetic materials 3-nitro-6-(3-nitro-1H-1,2,4-triazol-5-yl)-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole (4) and 6-(3,4-dinitro-1H-pyrazol-5-yl)-3-nitro-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole (12) were obtained via the Sandmeyer reaction. Further combination with energetic bases forms energetic salts 5–7 and 13–15 with good detonation performance and insensitivity. Notably, the neutral tricyclic energetic compounds 4 (P = 32.3 GPa, V_D = 8802 m·s^–1) and 12 (P = 31.6 GPa, V_D = 8627 m·s^–1) demonstrate detonation performance similar to that of 1,3,5-trinitroperhydro-1,3,5-triazine (RDX: P = 34.9 GPa, V_D = 8795 m·s^–1) and excellent mechanical sensitivities (4: IS > 40 J, FS = 288 N; 12: IS > 40 J, FS > 360 N) among fully C-nitrated cyclic azoles. This work establishes a scalable platform for synthesizing full C-nitro functionalization, providing new avenues to modulate detonation performance and favorable mechanical sensitivity for advanced high-energy-density materials applications.