4,5-Dicyano-1,2,3-Triazole—A Promising Precursor for a New Family of Energetic Compounds and Its Nitrogen-Rich Derivatives: Synthesis and Crystal Structures

Abstract

The nitrogen-rich compounds and intermediates with structure of monocyclic, bicyclic, and fused rings based on 1,2,3-triazole were synthesized and prepared by using a promising precursor named 4,5-dicyano-1,2,3-triazole, which was obtained by the cyclization reaction of diaminomaleonitrile. Their structure and configurational integrity were assessed by Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), and elemental analysis (EA). Additionally, fourteen compounds were further confirmed by X-ray single crystal diffraction. Meanwhile, the physical properties of four selected compounds (3·H2O, 6·H2O, 10·H2O, and 16) including thermal stability, detonation parameters, and sensitivity were also estimated. All these compounds could be considered to construct more abundant 1,2,3-triazole-based neutral energetic molecules, salts, and complex compounds, which need to continue study in the future in the field of energetic materials.

Syntheses and Applications of 1,2,3-Triazole-Fused Pyrazines and Pyridazines

“…There also exist recent patents describing use as herbicides [ 102 ] and plant growth attenuators [ 103 ]. 1,2,3-Triazolo[4,5-d]pyridazines : The most common synthetic method is reaction of a 4,5-dicarbonyl-1,2,3-triazole species with hydrazine to form the hydrazone, followed by acid or heat promoted cyclization [ 5 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 73 , 74 , 75 , 76 , 77 , 78 , 104 ]. The second most common method is treatment of the respective diaminopyridazine with nitrite [ 80 , 81 , 82 , 83 ].…”

“…Reports of forming 1,2,3-triazolo[4,5- d ]pyridazones or pyridazines using this method include those of Gilchrist [ 64 , 65 ], Milhelcic [ 66 ], Ramesh [ 67 ], Theocharis [ 68 ], Bussolari [ 69 ], Biagi [ 70 , 71 , 72 ], Abu-Orabi [ 73 ], Ramanaiah [ 74 ], Bankowska [ 75 ], and others [ 5 , 76 , 77 , 78 ].…”

Energetic Materials Based on N-substituted 4(5)-nitro-1,2,3-triazoles

“…1,2,3-Triazole nitro derivatives-five-membered heteroaromatic systems bearing three endocyclic nitrogen atoms and exocyclic explosophoric NO2 groups-are commonly used in the development of efficient high-energy compounds, including ionic ones, that exhibit enhanced technological and operational safety for various applications [9][10][11][12][13][14].…”

“…The aromatic nature provides the triazole heterocyclic molecule with high thermal and chemical stabilities and a low sensitivity to mechanical stimuli [9,10]. The three coupled nitrogen atoms united into the five-membered heterocyclic system preserve the energy potential of the azido group and impart quite a high enthalpy of formation to 1,2,3-triazoles [15].…”

“…The functionalization with supplemental energy-rich moieties in the form of NO2 groups promotes enhanced density and increases the number of oxidizing elements (oxygen balance) required to oxidize components and maximize the energetic potential of the overall system [16]. The capability of accepting various metal ions and oxoacid anions opens the door to the synthesis of various supramolecular ionic systems, including the oxygen-enriched ones in the active form, starting from cations of triazolium heterocycles [10]. Such ionic systems holds promise as energetic compounds, which concurrently combine low sensitivity to mechanical stimuli and high energetic performance [17].…”