From Tetranitromethane to Gem-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 ( 3 ) containing nitrogen-rich triazole and nitro-triazinane moieties. In addition, two of its analogues ( 4 and 5 ) 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, 3 shows promising heat of detonation ( Q = 5859 kJ kg –1 ), which is 2.8 times of TNM and higher than most of its mono ring-modified derivatives ( Q: 2076 to 5594 kJ kg –1 ). The detonation velocity and detonation pressure of 3 ( D v = 8964 m s –1 and P = 35.7 GPa) are competitive with those of RDX ( Q = 5763 kJ kg –1, D v = 8782 m s –1, and P = 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.