Assembling Nitrogen-rich, thermally Stable, and insensitive energetic materials by polycyclization

In pursuit of energetic materials which have equal energies and thermal stabilities, but lower sensitivities compared with hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and octahydro-1,3,5,7-tetranitro-1,3,5,7tetrazocine (HMX), a new fused N-heterocyclic framework, ditriazolo-1,2,4,5-tetrazine, 7 was designed and synthesized. Compound 7 exhibits a favorable decomposition temperature of 247 C benefiting from its good aromaticity which was studied by nucleus-independent chemical shift (NICS) and isochemical shielding surfaces (ICSS). Combined with moderate detonation properties (vD, 8544 m s(-1); P, 27.3 GPa) and low sensitivities (IS, > 40 J; FS, > 360 N), 7 may potentially be useful as a secondary energetic in practical applications to replace RDX. Hydrazinium salt 12 has a thermal stability of 221 C, and excellent detonation properties (vD, 9088 m s(-1) ; P, 32.3 GPa), which are comparable with those of HMX. These contributions highlight the fused N-heterocyclic framework as a potential energetic backbone and provide new thinking to the chemistry of polycyclic heterocycles.

Automated summary

This article introduces a new fused N-heterocyclic framework, named ditriazolo-1,2,4,5-tetrazine (7). Compound 7 exhibits lower sensitivities and suitable decomposition temperature compared with RDX and HMX, making it a potential candidate as a secondary energetic material to replace RDX in practical applications.