Herein, a series of esteryl-bridged energetic compounds were prepared using a simple and efficient esterification approach. All the compounds were fully characterized by IR spectroscopy, multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, thermogravimetric analysis (TG), and differential scanning calorimetry (DSC). Structures of 1 and 4 were further confirmed by single crystal X-ray diffraction. Energetic performance was evaluated by EXPLO5 based on the measured densities and calculated heats of formation (Gaussian 09). These fluorodinitroethyl esters have good thermal stabilities (190.7–208.3 °C) and high densities (1.81–1.90 g cm−3). Detonation pressures and velocities of 1–5 fall in the range of 27.4–36.6 GPa and 7870–8459 m s−1, respectively. Sensitivity data based on impact and friction tests show that these compounds are insensitive (IS = 27.6–40 J; FS > 360 N). Moreover, two of the representative compounds 1 and 4 exhibit the desired melting points (1: 85.0 °C; 4: 94.7 °C) as the ideal melt cast explosives, relatively high detonation properties (D = 8459, 8196 m s−1; P = 36.6, 29.8 GPa), as well as relatively low sensitivities (IS = 30.5, 27.6 J; FS > 360 N).
Pyrazole derivatives with polynitro groups were extensively researched in energetic material field as they show high energy density and excellent detonation properties, but the specific synthesis process still encounters challenges. In this paper, we firstly combined trinitromethyl, dinitroethyl, oxadiazolyl moieties with pyrazole, successfully designed and synthesized three novel poly-nitro pyrazole energetic compounds by nitration. Their structural features were investigated using single-crystal X-ray diffraction, nuclear magnetic resonance, infrared spectroscopy. 3-(3,5-Dinitro-1 H -pyrazol-4-yl)-1,2,4-oxadiazol-5(4 H )-one ( 12 ) possessed a superior thermal stability (235.1 °C) due to the presence of strong conjugated interaction in this structure. Among all, 3-nitro-1-(trinitromethyl)-1 H -pyrazole-5-carboxylic acid ( 8 ) exhibited a good thermal stability (163.7 °C), a high density of 1.829 g cm −3 at 298 K in combination with excellent detonation properties ( D : 8747 m s −1 ; P : 33.613 GPa). The results indicate that three compounds have promise to act as novel energetic materials and the synthesis provides a direction for polynitro compounds and oxadiazol based energetic compounds.
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