Novel energetic salts of N-methylene-C-bridged nitrogen-rich heterocycle 5-((5-amino-tetrazol-1-yl)methyl)-1,2,4-triazole-3,4-diamine: Syntheses, characterization, and properties

Abstract

Nitrogen-rich energetic salts have attracted considerable interest recently, due to their fascinating thermal stability and energetic performance. In this work, N-methylene-C-bridged nitrogen-rich heterocycle (5-((5-amino-tetrazol-1-yl)methyl)-1,2,4-triazole-3,4-diamine (ATMTDA) (1)) were synthesized and its nitrogen-rich energetic salts ((ATMTDA)2[(HATMTDA)(DCNM)]2H2O (2), (HATMTDA)NO3 (3), (H2ATMTDA)(NO3)2 (4), (HATMTDA)ClO4 (5), (HATMTDA)NTO (6), and (H2ATMTDA)(PA)2(H2O)2 (7)) were prepared. These energetic compounds were fully characterized by elemental analysis, FTIR spectroscopy and single-crystal X-ray diffraction analysis. The NBO charge of 1 was calculated by density functional theory, to understand which N atoms was more vulnerable to attack by H protons to become cations. And the thermal stability of these compounds was studied by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) with acceptable results (Tdec > 190 °C). All of the studied compounds except for compound 5 (FS=216 N, IS=3 J) exhibited less sensitivities than RDX ((FS=120 N, IS=7.4 J), and compound 1 (8.62 km/s, 25.71 GPa) showed good detonation performance. All of the results illustrated the potential application of the compounds as energetic materials.