Energetic Triazolo‐Triazolo‐Furazano‐Pyrazines: A Promising Fused Tetracycle Building Block with Diversified Functionalities and Properties

Abstract

AbstractIn this study, high energy materials (HEMs) derived from 1,2,4‐triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazine (TTFP) substituted with −NH2, −NHNO2, −ONO2, −NO2, and −N3 explosophoric groups were designed and computationally characterized. Density functional calculations with B3PW91/6‐31G(d,p) method were used to explore the optimized structures, energetic properties, and sensitivity of TTFP derivatives. It is found that the TTFP is an effective molecular backbone for improving the energy content and energetic performance of the designed compounds. The effect of various explosophoric groups on energy content, density, detonation performance, and sensitivity was investigated. The energetic evaluation indicated that TTFP derivatives having −NHNO2 (F4), −ONO2 (F5), and −NO2 (F6) groups demonstrate good detonation performances and exceed the performance of TNT and close to that of RDX. Compounds F4‐F6 displays the best energetic properties (density > 1.85 g/cm3, detonation velocity >8.30 km/s, detonation pressure > 32.0 GPa). Considering the energetic properties, the TTFP backbone can be regarded as an energy‐rich unit, which can be substituted with suitable explosophoric groups for constructing HEMs.