From Tetranitromethane to -Dinitro-Bridged Nitrogen-Rich Heterocyclic Compound: Achieving High Heat of Detonation.

Improving the detonation performance of tetranitromethane (TNM) by introducing energetic moieties is an intriguing area in the field of energetic materials. Incorporation of a mono nitrogen-rich skeleton into TNM usually results in unsatisfactory detonation performance. Now, we reported the design and synthesis of an advanced TNM-like molecule () containing nitrogen-rich triazole and nitro-triazinane moieties. In addition, two of its analogues ( and ) were also obtained. Taking advantage of the positive heat of formation brought by triazole and triazinane rings and high-density properties donated by many nitro groups, shows promising heat of detonation ( = 5859 kJ kg), which is 2.8 times of TNM and higher than most of its mono ring-modified derivatives (: 2076 to 5594 kJ kg). The detonation velocity and detonation pressure of ( = 8964 m s and = 35.7 GPa) are competitive with those of RDX ( = 5763 kJ kg, = 8782 m s, and = 34.7 GPa). Structural modification by using triazole and nitro-triazinane rings may be helpful in exploring more TNM derivatives and other types of high-performance explosives.