Theoretical design of bis-azole derivatives for energetic compounds

Bis-azole derivatives are a new class of energetic materials with features that include high nitrogen content, high heat of formation (HOF), high detonation performance and insensitivity to external stimuli. In this paper, 599 new bis-azole compounds were designed in a high-throughput fashion using bis-azole molecules of high density and high thermal decomposition temperature as the basic structure, and high energy groups such as nitro (–NO(2)) and amino groups (–NH(2)) as substituents. The molecular geometry optimization and vibration frequency analysis were performed using the DFT-B3LYP/6-311++G(d,p) method. The calculation results show that none of bis-azole derivatives exhibit a virtual frequency. Additionally, the density, heat of formation and characteristic height (h(50)) of the above compounds were obtained. Detonation performances were predicted by the Kamlet–Jacobs equations, and their structures and performances were studied. Furthermore, correlations between the performance parameters and the parent structure of the molecule, the number of substituting group and configuration were summarized, revealing promising potential candidates for high-energy density materials (HEDMs).