4,4′,5,5′-Tetraamino-3,3′-azo-bis-1,2,4-triazole and the electrosynthesis of high-performing insensitive energetic materials

Abstract

Herein, we have demonstrated that electrochemical synthesis of high-performing, insensitive energetic materials in an environmentally friendly manner is possible in a single step from readily available precursors using a synthetic...

Continuous and Electrochemical Synthesis of 2,2’,4,4’,6,6’‐Hexanitrostilbene

“…In order to confirm this conclusion, the solution after the reaction was analyzed by ultraviolet spectroscopy with a maximum absorption peak at 613 nm (see Figure S6). To further confirm the substance, cyclic voltammetry results for a deep blue solution are used, [44,45] the results are shown in Figure 2a.…”

4,4′-Dinitrimino-5,5′-diamino-3,3′-azo-bis-1,2,4-triazole: A High-Performing Zwitterionic Energetic Material

“…26 4.3. 3,4,5-Triamino-1,2,4-triazole (1). Guanazine was synthesized according to the literature procedure.…”

“…Recently, our research group synthesized the novel insensitive energetic material 4,4′5,5′-tetraamino-3,3′-azo-bis-1,2,4-triazole (TAABT) through the electrolytic oxidation of 3,4,5triamino-1,2,4-triazole (guanazine) under mildly basic conditions. 1 TAABT demonstrated remarkable stability with decomposition temperatures approaching 300 °C, impact sensitivities greater than 40 J, and friction sensitivities greater than 360 N. Additionally, it has been well established that high-nitrogen azo-bridged materials, such as TAABT, may have relatively low environmental toxicity in comparison to traditional energetics due to the relatively benign detonation products. 2 The growing desire for insensitive high explosives 3,4 and the need to replace environmentally and physiologically toxic legacy materials (e.g., RDX), 5−8 makes TAABT a desirable scaffold molecule for novel energetic formulations.…”

“…Additionally, the protic nature of the nitramine moiety allows for the opportunity to generate numerous high-performing energetic salts or hydrogen-bonded cocrystalline materials to tune the thermal stability and performance. We synthesized energetic salts incorporating the hydrazinium, hydroxylammonium, ammonium, 5-aminotetrazolium, and 3,6,7-triamino- [1,2,4]triazolo [4,3-b] [1,2,4]triazolium (TATOT) cations (Scheme 1b) via facile metathesis reactions. Additionally, we were able to effectively generate a DNDAABT cocrystal with TAABT (8) (Scheme 1c).…”

Design of functionalized bridged 1,2,4-triazole N-oxides as high energy density materials and their comprehensive correlations

“…[8][9][10][11] Prominent families are triazole and tetrazole compounds that have been studied over the last couple of years with growing interest. [12][13][14][15][16] Compared to the single heterocycle ring, bis-azoles with C-C connection show that promising properties arose from the higher heat of formation, which can be proved in good examples 5,5 0 -bistetrazoles 17 and 5,5 0 -bistriazoles. 18 A further way of developing energetic azoles is introducing Noxides onto the ring to improve the oxygen balance without losing energy or stability.…”