It has long been a driving force in the development of energetic materials to hunt for novel high-energy density materials (HEDMs) with high energy and good stability. Recently, the noncovalent self-assembly strategy of energetic anions and cations to generate HEDMs is an effective strategy for introducing an oxidizer and fuel separately into the energy system. In this study, bis(1,2,4-triazolyl)triazene containing triazene (−NNNH−) and oxidant molecules (i.e., HNO3 and HClO4) were selected as high-energy ions to develop new high energy materials by using noncovalent self-assembly. The experimental results showed that three exemplary compounds possess excellent detonation pressure and detonation velocity (P C–J: 22.8–29.3 GPa and D: 7425–8135 m s–1), which are comparable to the classical explosive trinitrotoluene (TNT) (P C–J: 19.5 GPa and D: 6881 m s–1) as well as 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX) (P C–J: 34.9 GPa and D: 8795 m s–1). Moreover, 1 and 3 exhibit low mechanical sensitivities (IS: 40 J and IS: 70 J). Thus, 1 and 3 have great potential as insensitive energetic materials. Especially, these energetic assemblies have excellent laser-ignited combustion properties and can be used as candidates for low sensitivity propellants.

The oxidation of amines based on nitrogen-rich heterocycles is one of the appealing alternatives for promising nitro derivatives. Herein, we present a continuous-flow process to achieve oxidation of these amines to their nitro derivatives, taking advantage of hydrogen peroxide as an environmentally benign and inexpensive oxidant. Facile and sustainable access to valuable nitro compounds was ensured. The utility of the present continuous-flow oxidation process was demonstrated by synthesizing promising energetic compounds 5-amino-3-nitro-1,2,4-triazole (ANTA) and 1-methyl-3,4,5-trinitropyrazole (MTNP) on a multigram scale.

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