Molecule design and properties of bridged 2,2-bi(1,3,4-oxadiazole) energetic derivatives.

A series of bridged 2,2-bi(1,3,4-oxadiazole) energetic derivatives were designed and their geometrical structures, electronic structures, heats of formation, detonation properties, thermal stabilities and thermodynamic properties were fully investigated by density functional theory. The results showed that the -N group and the -N- bridge play an important role in improving heats of formation of these 2,2-bi(1,3,4-oxadiazole) derivatives. The calculated detonation properties indicated that the -NF group and the -N- bridge were very useful for enhancing the heats of detonation, detonation velocities and detonation pressures. Twenty-four compounds were found to possess equal or higher detonation properties than those of RDX, while 14 compounds had equal or higher detonation properties than those of HMX. The analysis of the bond-dissociation energies suggested that the -CN group was the effective structural unit for increasing the thermal stabilities while the -NHNH group decreased these values. Overall, taking both the detonation properties and thermal stabilities into consideration, 22 compounds (A4, A6, A8, A9, B4, B9, C2, C3, C4, C5, C7, C, C9 D4, D8, D9, E9, F4, F9, G9, H4 and H9) were selected as the potential candidates for high-energy-density materials.