New zwitterionic compounds based on 1-(tetrazol-5-yl)-1,2,4-triazole: High-energy, low-sensitivity energetic materials

• For the first time, two zwitterionic compounds based on the 1-(tetrazol-5-yl)−1,2,4-triazole backbone were synthesized. • All novel compounds exhibit acceptable thermal stability ( T d =182–238 °C), good detonation performance ( v D =8200–8916 m s −1 , P =23.6–28.6 GPa), and low sensitivity (IS ≥ 31 J, FS ≥ 324 N). Conjugated bicyclic triazole-tetrazole backbones, with their excellent stability and high nitrogen content, are important frameworks for the design of high-energy, low-sensitivity compounds. In this study, a novel amino-substituted 1-(tetrazol-5-yl)-1,2,4-triazole zwitterionic compound 1 and its nitrated derivatives 2 – 9 were synthesized. All compounds were characterized by IR, 1 H and 13 C NMR spectroscopy, and elemental analysis. The structures of the neutral compounds 1 and 2 , ammonium salt 3 , hydrazonium salt 5 , and triaminoguanidinium salt 9 , were determined through X-ray single-crystal diffraction. All compounds exhibited acceptable thermal stability ( T d = 182°C-238°C), good detonation performance ( v D = 8393–8916 m s −1 , P = 23.6–28.6 GPa), and low sensitivity (FS ≥ 324 N, IS ≥ 31 J). Additionally, the compounds demonstrate favorable measured densities (ρ = 1.66 g cm −3 –1.75 g cm −3 ). Notably, salt 8 possessed excellent detonation velocity ( v D = 8916 m s −1 ), decent thermal stability ( T d = 219°C), and low sensitivity (FS = 330 N, IS = 33 J), making it a promising candidate for high-energy, low-sensitivity energetic materials.