Tri-explosophoric groups driven fused energetic heterocycles featuring superior energetic and safety performances outperforms HMX

Abstract

The design and synthesis of novel energetic compounds with integrated properties of high density, high energy, good thermal stability and sensitivities is particularly challenging due to the inherent contradiction between energy and safety for energetic compounds. In this study, a novel structure of 4-amino-7,8-dinitropyrazolo-[5,1-d] [1,2,3,5]-tetrazine 2-oxide (BITE-101) is designed and synthesized in three steps. With the help of the complementary advantages of different explosophoric groups and diverse weak interactions, BITE-101 is superior to the benchmark explosive HMX in all respects, including higher density of 1.957 g·cm−3, highest decomposition temperature of 295 °C (onset) among CHON-based high explosives to date and superior detonation velocity and pressure (D: 9314 m·s−1, P: 39.3 GPa), impact and friction sensitivities (IS: 18 J, FS: 128 N), thereby showing great potential for practical application as replacement for HMX, the most powerful military explosive in current use.

Multi-energetic group synergy driven design and synthesis of [1,2,4]triazolo[5,1-c][1,2,4]triazine-fused energetic compounds

“…19,20 Recently, BITE-101 , which contains a stabilizing group (C–NH 2 ) and energy-enhancing groups (C–NO 2 and N → O) in a fused ring system, was reported by our group, achieving a good balance between energy and safety. 21…”

Trinitromethyl Energetic Groups Enhance High Heats of Detonation

“…Over the past few decades, the design and synthesis of high energy density materials (HEDMs) has attracted more and more attention. − After the development of HEDMs from RDX, HMX to CL-20, researchers have conducted in-depth research on the structure activity relationship of energetic compounds. − Researchers believe that the introduction of backbones which store more chemical energy is an important way to improve the detonation performance of energetic materials, such as heat of detonation ( Q ), detonation velocity ( D ), and detonation pressure ( P ). − Therefore, the most common strategy for synthesizing new HEDMs is to combine single heterocycles or fused backbones, which have high enthalpies of formation (Δ H f ), with energetic groups such as nitro, dinitromethyl, , or trinitromethyl groups. , Among the currently known energetic backbones, single heterocycles have been widely studied because of their simple structure and convenient synthesis. , …”

Thermally Stable and Insensitive Energetic Cocrystals Comprising Nitrobarbituric Acid Coformers

“…The requirement of energetically enhanced, safe, and probably green energetic materials constantly paved the way for futuristic development. − The development of new energetic materials is slow compared to other areas such as devices, pharmaceuticals, metal catalysis, etc. To make new energetic materials that can be utilized directly in the field, stringent requisites like cost-effective synthesis, scale-up feasibility, superior performance, insensitivity, and chemical and thermal stability need to be fulfilled. , In most cases, the newly developed energetic materials are still unable to completely replace currently used compounds in the explosives and propellants because of various problems, including high preparation cost, thermal instability, sensitivity to mechanical stimuli, and chemical incompatibility. , The contradiction between high performance and safety is still very prominent because there are often casualties and asset losses caused by an unintended explosion of compounds. To overcome these limitations, the cocrystallization method has attracted significant attention in the field of energetic materials. − In cocrystallization, two or more energetic or nonenergetic components are combined in a crystal lattice with a defined stoichiometric ratio, linked together through noncovalent interactions.…”