Harnessing triazole–oxadiazole–trinitromethyl moieties in the synthesis of insensitive energetic material with enhanced detonation performance

Abstract

The nitrogen-and oxygen-rich azole-based high energetic compound 3,3′-(2-(trinitromethyl)-2H-1,2,3-triazole-4,5-diyl)-bis(1,2,4-oxadiazole) (5) was synthesized from a readily accessible bis-cyano-substituted-azole in three steps with an overall good yield. The reaction sequence was even successful on the gram scale. The five-membered azole backbone with a –C(NO₂)₃ group contributes to boosting energetic properties of the molecule. The synthesized compounds were fully characterized using NMR, IR, HRMS, and TGA–DSC studies. X-ray diffraction analysis established the molecular topology of the desired compound. The molecule showed promising energetic performance with a good oxygen balance (−31.6%), high positive heat of formation (+679.8 kJ mol⁻¹), and high detonation pressure (P = 29.6 GPa) and velocity (D_v = 8356 m s⁻¹), which are close to those of PETN, superior to those of HNS, and surpass those of TNT. Hirshfeld surface analysis gives insights into the molecule's sensitivity.