Strategies Toward Syntheses of Triazolyl- or Triazolium-Functionalized Unsymmetrical Energetic Salts

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Triazolyl-functionalized monocationic energetic salts ( 2a − m ) were prepared through reactions of 1-(chloromethyl)-1H-1,2,4-triazole with 1-methylimidazole, 1-methyl-1,2,4-triazole, or 4-amino-4H-1,2,4-triazole in the presence of NaI, followed by metathetical reactions with equivalent silver salts. Subsequent protonation with corresponding acids gave rise to triazolium-functionalized diquaternary salts ( 3a − c ). Direct treatment of neutral 1-(1 H -imidazole-1-yl)methylene-1 H -1,2,4-triazole, which was prepared by reaction of 1-(chloromethyl)-1H-1,2,4-triazole with imidazole in the presence of a base, with acids in methanol or metathesis with silver salts after quaternization with methyl iodide gave rise to the corresponding diquaternary energetic salts 5a − c and 7a − d, respectively. All of the energetic salts were characterized by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) and density determinations. The majority of them exhibit good thermal stability and relatively high density. The synergistic effect of two energetic rings in cations and the effect of anions on their preparation and physicochemical properties were examined and are discussed. The densities, standard enthalpies of formation, detonation pressures, detonation velocities, and specific impulse values for the unsymmetric dicationic energetic salts were calculated.