Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials.

New energetic fully-substituted polynitrobenzene derivatives were synthesized the reaction of 1,3,5-trichloro-2,4,6-trinitrobenzene (TCTNB) with 1,2,4-triazole followed by the nucleophilic substitution of the halo groups by aqueous ammonia or sodium azide. These compounds were charactered by H NMR, C NMR and HRMS. Additionally, the structures of amino derivatives 6, 8 and azido derivative 7 were further confirmed by single crystal X-ray diffraction analysis. Their decomposition temperatures and impact sensitivities were also determined. The derivative 1,2-di-1-triazol-4,6-diamino-3,5-dinitrobenzene (8) exhibits good thermal stability ( = 314 °C) and low impact sensitivity (IS = 30 J), which are both superior to that of TNT ( = 295 °C, IS = 15 J). These synthesized compounds showed high heat of formation ranging from 31.77 to 1014.68 kJ mol, and reasonable detonation velocities and pressures.