Conjugated Pyrazole-Triazole/Oxadiazole Derivatives via Nitro Functionalization: Toward High-Performance Energetic Materials

Abstract

Through the strategic integration of 3,4-dinitropyrazole with trinitromethyltriazole and oxadiazolone units, two novel asymmetric bicyclic energetic materials, 5-(3,4-dinitro-1H-pyrazol-5-yl)-3-(trinitromethyl)-1H-1,2,4-triazole (DNP-TNF) and 3-(3,4-dinitro-1H-pyrazol-5-yl)-1,2,4-oxadiazol-5(4H)-one (DNP-OO), were successfully designed and synthesized. Systematic testing revealed that the nitro-functionalized extended conjugated structure achieves excellent detonation performance (D = 9273 and 8485 m·s^-1, P = 39.4 and 31.3 GPa) while maintaining moderate thermal stability (T_dec = 150.7 and 198.5 °C) and mechanical sensitivity (IS = 8.9 and 12 J, FS = 168 and 240 N). Furthermore, DNP-OO exhibits a suitable melting point (T_m = 82.2 °C) and decomposition temperature, demonstrating its potential as a candidate for melt-cast explosive applications.