Combination of Triazole and Triazolone Ring Skeletons for Construction of Heat-Resistant Energetic Compounds

Triazolone is a nitrogen-rich heterocyclic framework with broad application prospects in heat-resistant energetic compounds. However, because of the lack of good modification means for triazolone rings, their application in heat-resistant energetic compounds is limited. In this study, a novel family of energetic compounds incorporating a triazole-triazolone architecture was synthesized via cyclocondensation between carbohydrazide and amidoxime derivatives. The resulting compounds display outstanding thermal stability (Td = 246–373 °C), excellent detonation properties (Dv = 7387 to 8670 m·s–1), reduced mechanical sensitivities (IS > 15 J, FS > 360 N), and positive heats of formation (ΔHf = 310.9–585.8 kJ·mol–1). Notably, compound 4′,5-diamino-1′,4′-dihydro-2H,5′H-[3.3′-bi(1,2,4-triazol)]-5′-one (5) exhibits superior comprehensive performance, including enhanced thermal decomposition temperature (Td = 373 °C), and low sensitivity (IS > 40 J, FS > 360 N), competitive detonation properties (Dv = 8101 m·s–1), exceeding heat-resistant explosive Hexanitrostilbene (HNS: Td = 318 °C, Dv = 7612 m·s–1, IS = 5 J, FS = 240 N) in key metrics. Thus, 5 is suitable for use as an energetic material that is both insensitive and superheat resistant.