An Alliance of Polynitrogen Heterocycles: Novel Energetic Tetrazinedioxide-Hydroxytetrazole-Based Materials

Abstract

Energetic materials constitute one of the most important subtypes of functional materials used for various applications. A promising approach for the construction of novel thermally stable high-energy materials is based on an assembly of polynitrogen biheterocyclic scaffolds. Herein, we report on the design and synthesis of a new series of high-nitrogen energetic salts comprising the C-C linked 6-aminotetrazinedioxide and hydroxytetrazole frameworks. Synthesized materials were thoroughly characterized by IR and multinuclear NMR spectroscopy, elemental analysis, single-crystal X-ray diffraction and differential scanning calorimetry. As a result of a vast amount of the formed intra- and intermolecular hydrogen bonds, prepared ammonium and amino-1,2,4-triazolium salts are thermally stable and have good densities of 1.75–1.78 g·cm−3. All synthesized compounds show high detonation performance, reaching that of benchmark RDX. At the same time, as compared to RDX, investigated salts are less friction sensitive due to the formed net of hydrogen bonds. Overall, reported functional materials represent a novel perspective subclass of secondary explosives and unveil further opportunities for an assembly of biheterocyclic next-generation energetic materials.

Low-dimensional lateral heterojunctions made of hexagonal boron nitride and carbon materials as efficient electrocatalysts for the chlorine evolution reaction: a study of DFT and machine learning

“…1,2 An integral part of this cycle involves chlorinated organic compounds (Cl org ), commonly utilized in chemical production elds such as the fabrication of energetic materials. [3][4][5][6] This process, however, invariably results in the generation of signicant volumes of chlorine-laden wastewater. The unregulated disposal of such wastewater poses severe threats to waterbodies and soil.…”

Straightforward and Efficient Protocol for the Synthesis of Pyrazolo [4,3-b]pyridines and Indazoles

“…Polynitrogen heterocycles have found their application in various fields of chemistry and material science, such as perspective high-energy density compounds [ 1 , 2 , 3 , 4 ], purine antimetabolites used in the treatment of cancer [ 5 ], chemosensors [ 6 ] and many others. In particular, pyrazolo [4,3- b ]pyridines are of considerable interest due to their diverse biological activity.…”

Substituted tetrazoles with N-oxide moiety: critical assessment of thermochemical properties

“…Literature survey showed that only salts 3a and 3b , as well as a salt 3 with 4-aminotriazole cation, 14 are known from the list of salts studied in this work. 2 N -Oxide isomers of salts 1 are considered in ref.…”

“…These ionic compounds are usually synthesized through scalable convenient procedures either upon direct neutralization of the corresponding acids or via a cation metathesis route. [11][12][13][14] As a rule, energetic salts have a high nitrogen content and do not exhibit corrosive properties, which ultimately results in their profoundly reduced hazardous nature. From the materials science point of view, the functional properties of energetic salts are easily modulated through a combination of different cations and anions or via a structural modification of ionic components.…”

“…Literature survey showed that only salts 3a and 3b, as well as a salt 3 with 4-aminotriazole cation, 14 In this work, we have focused on identifying the energy aspects of these salts, namely, on assessing their enthalpies of formation in the solid state. As is known, 25,26 the detonation and ballistic properties of energy-rich components can be estimated from the corresponding values of densities and enthalpies of formation.…”