Bis(dinitropyrazolyl)methanes spruced up with hydroxyl groups: high performance energetic salts with reduced sensitivity

Abstract

With an aim to improve the overall physical stability of high-performing 3,5-dinitro-functionalised bispyrazolymethanes, a hydroxyl functionality was introduced at the fourth position to obtain 1,1′-methylenebis(3,5-dinitro-1H-pyrazol-4-ol) and its energetic salts. Superior oxygen balance and energy in comparison to the amino substituent at the 4th position and enhanced sensitivity with respect to the nitro and azido substituents helped in unlocking the potential of less explored N-alkylated-4-hydroxy-3,5-dinitropyrazoles. Fine-tuning of properties via dicationic salt formation, which is not feasible in any other reported symmetrically connected pyrazole-based energetic materials, resulted in improved physical and thermal stabilities, as well as energetic performance. Hirshfeld surface analysis, electrostatic potential analysis, the study of aromaticity and weakest Mayer-bond order analysis helped further in studying the structure–property relationship of the synthesized compounds with respect to different reported methylene-bridged symmetrical compounds.