Triazole-substituted nitroarene derivatives: Synthesis, characterization, and energetic studies

Abstract

A series of dense and energetic polynitroaryl-1,2,4-triazoles were synthesized through the nitration of aryl-1,2,4-triazoles. The Cu-catalyzed/base-mediated coupling reactions of haloarenes with 1,2,4-triazoles delivered N-aryl-1,2,4-triazoles. These new nitro-rich-aryltriazoles were characterized by analytical and spectroscopic methods. The solid-state structures of most of these compounds were established by X-ray diffraction analysis. Their thermal properties were determined by differential scanning calorimetry-thermogravimetric analysis. Their heats of formation (HOFs) and crystal densities were also calculated. The densities of the synthesized compounds ranged from 1.40 to 1.85 g cm-3. Some of these newly synthesized compounds exhibited high positive HOFs, good thermal stabilities, high densities, and reasonable detonation velocities and pressures. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.