Manipulating nitration and stabilization to achieve high energy

Nitro groups have played a central and decisive role in the development of the most powerful known energetic materials. Highly nitrated compounds are potential oxidizing agents, which could replace the environmentally hazardous used materials such as ammonium perchlorate. The scarcity of azole compounds with a large number of nitro groups is likely due to their inherent thermal instability and the limited number of ring sites available for bond formation. Now, the formation of the first azole molecule bonded to seven nitro groups, 4-nitro-3,5-bis(trinitromethyl)-1H-pyrazole (4), by the stepwise nitration of 3,5-dimethyl-1H-pyrazole is reported. Compound 4 exhibits exceptional physicochemical properties with a positive oxygen balance (OB(CO2) = 13.62%) and an extremely high calculated density (2.04 g cm(−3) at 100 K). This is impressively high for a C, H, N, O compound. This work is a giant step forward to highly nitrated and dense azoles and will accelerate further exploration in this challenging field.