Searching for high performance asymmetrically substituted teterazine energetic materials based on 3-hydrazino-6-(1H-1,2,3,4-tetrazol-5-ylimino)-s-tetrazine

Tetrazine compounds are promising candidates of high performance energetic materials (EMs). For the purpose of exploring high performance asymmetrically substituted teterazine explosives, 3-hydrazino-6-(1H-1,2,3,4-tetrazol-5-ylimino)-s-tetrazine was selected as the precursor and a series of teterazine EMs were prepared based on three synthetic strategies. All the obtained compounds were fully characterized and the crystal structures of seven compounds were further confirmed by single crystal X-ray diffraction. The thermal dynamics and thermal safety parameters, the detonation properties and impact sensitivities were also obtained. The results revealed that compounds 15–17 show excellent energetic properties (detonation velocities > 9000 m·s⁻¹, detonation pressures > 30 GPa) and have impact sensitivities (8–12 J) that comparable or lower than RDX. Compounds 9–13 are insensitive to impact and have detonation velocities range from 8452 to 8775 m·s⁻¹. These compounds can be good candidates of high performance secondary explosives or insensitive EMs.