Incorporating Energetic Moieties into Four Oxadiazole Ring Systems for the Generation of High‐Performance Energetic Materials

The synthesis of three neutral 3,3′‐di(1,2,5‐oxadiazol‐3‐yl)‐5,5′‐bi(1,2,4‐oxadiazole) structures in combination with different energetic moieties such as nitramino, trinitroethylamino, and N ‐nitrated trinitroethylamino is presented. In addition, a novel family of energetic salts based on 4,4′‐([5,5′‐bi(1,2,4‐oxadiazole)]‐3,3′‐diyl)‐bis(1,2,5‐oxadiazol‐3‐nitramide) is synthesized. The new compounds ( 4 , 6 – 18 ) are characterized by IR and multinuclear NMR spectroscopy and elemental analysis. The structures of 4 ⋅2 C 4 H 8 O 2 , 9 , 13 , 15 , and 16 are further confirmed by single‐crystal X‐ray diffraction studies. The thermal stabilities of 4 and 6 – 18 are determined by differential scanning calorimetry. Most of the new compounds have high densities (1.72–1.93 g cm −3 ) measured using a gas pycnometer (25 °C). Energetic evaluation indicates that they also have good detonation pressures and velocities ( P : 26.4–41.9 GPa; D : 8218–9550 m s −1 ).