Azo-Bridged Triazole Macrocycles: Computational Design, Energy Content, Performance, and Stability Assessment.

Abstract

Oxadiazole and triazole are extensively investigated heterocyclic scaffolds in the development of energetic materials. New energetic molecules were designed by replacing 1,2,5-oxadiazole with 2H-1,2,3-triazole in the reported conjugated macrocyclic systems to assess the influence on the energetic properties and stability. In addition, nitro groups were introduced in triazole units (N-functionalization) to improve the energetic performance. Energetic properties, including heat of formation, oxygen balance, density, detonation pressure and velocity, and impact sensitivity, were estimated for these triazole-based macrocycles. The replacement of 1,2,5-oxadiazole with 2H-1,2,3-triazole and 2-nitro-1,2,3-triazole significantly enhances the energy content, detonation performance, and noncovalent interactions. The theoretically computed energetic properties of triazole-based macrocycles reveal high positive heats of formation (1507-2761 kJ/mol), oxygen balance (-88.8 to -22.8%), high densities (1.87-1.90 g/cm3), superior detonation velocities (8.41-9.52 km/s), pressures (26.64-40.55 GPa), acceptable impact sensitivity (27-40 cm), and safety factor (51-290). The overall energetic assessment highlights triazole-based macrocycles as a potential framework that will be useful for developing advanced energetic materials.