[1,2,4]Triazolo[1,5-d][1,2,4]oxadiazole ring system – A novel building block for creating energetic compounds

et al. 2023

Mater. Chem. Front.

Section: Introductionmentioning

confidence: 99%

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

Liu

et al. 2023

Mater. Chem. Front.

“…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. , …”

Section: Introductionmentioning

confidence: 99%

Trinitromethyl Energetic Groups Enhance High Heats of Detonation

Chen

Dou

ACS Appl. Mater. Interfaces

et al. 2023

Self Cite

The introduction of groups with high enthalpies of formation can effectively improve the detonation performance of the compounds. A series of novel energetic compounds (10–13) with high enthalpies of formation, high density, and high nitrogen–oxygen content were designed and synthesized by combining gem-polynitromethyl, 1,2,4-oxadiazole, furoxan, and azo groups. All the new compounds were thoroughly characterized by IR, NMR, elemental analysis, and differential scanning calorimetry. Compounds 10 and 11 were also further characterized with single-crystal X-ray diffraction. Compound 11 has high density (1.93 g cm–3), high enthalpy of formation (993.5 kJ mol–1), high detonation velocity (9411 m s–1), and high heat of detonation (6889 kJ kg–1) and is a potentially excellent secondary explosive.

“…Energetic compound with fused-ring conjugated backbones have a tendency to enhance the overall performance such as desirable energy properties and thermal stability . In recent years, a large number of fused nitrogen-rich heterocycles, − such as triazolopyridine, triazolo-1,2,4-triazine, bitriazolo-1,2,3,4-tetrazine, tetrazolo-1,2,4,5-tetrazine, and triazolo-1,2,4,5-tetrazine, have been reported. Most of them exhibit balanced energy and safety, especially chemical stability.…”

Section: Introductionmentioning

confidence: 99%

Energetic Gem-dinitro Salts with Improved Thermal Stability by Incorporating with A Fused Building Block

ACS Appl. Mater. Interfaces

Wang

Liu

et al. 2022

Self Cite

Thermal stability is one of the most significant properties for the safety of energetic materials, finding a stable skeleton with suitable energetic groups is always a primary test. In this work, an unusual aminohydrazone cyclization strategy was used in the synthesis of a new series of gem-dinitro 1,2,4-triazolo[4,3-b][1,2,4,5]-tetrazine compounds with desirable thermal stability (≥197 °C). All of the new compounds were fully characterized by infrared (IR), NMR, differential scanning calorimetry, single crystal X-ray diffraction, and elemental analysis. The decomposition temperature of potassium salt 2 is 288 °C, reaching the level of HMX. All of these performances have demonstrated the effective synthesis strategy for innovatively combining geminal dinitro groups with fused rings.