3-Methyl-1,2,3-triazolium-1N-dinitromethylylide and the strategy of zwitterionic dinitromethyl groups in energetic materials design

Abstract

Fully characterized energetic material containing a unique zwitterionic dinitromethyl functional group.

Synthesis of (5-Iminio-4,5-dihydro-1,3,4-oxadiazol-2-yl)tetrazol-1-ide: A Zwitterionic Compound Containing a Tetrazole Anion as a Promising Blunt Energetic Material

“…11 The formation of zwitterionic compounds is another effective way to improve the safety of energetic materials. Over the past years, there has been sustained research activity in zwitterionic compounds, such as zwitterionic compounds related to tetrazine dioxides 12 , tetrazazpentalenes 13 , and triazoles [14][15][16][17][18] . Studies have shown that zwitterionic energetic materials can improve performance by increasing density and stability through electrostatic interactions within the same molecule.…”

“…Over the past years, there has been sustained research activity in zwitterionic compounds, such as zwitterionic compounds related to tetrazine dioxides, 12 tetrazazpentalenes, 13 and triazoles. [14][15][16][17][18] Studies have shown that zwitterionic energetic materials can improve performance by increasing density and stability through electrostatic interactions within the same molecule. 14,15 Zwitterionic compounds are electronically neutral and carry both positive and negative charges in the same molecule.…”

“…[14][15][16][17][18] Studies have shown that zwitterionic energetic materials can improve performance by increasing density and stability through electrostatic interactions within the same molecule. 14,15 Zwitterionic compounds are electronically neutral and carry both positive and negative charges in the same molecule. In contrast to classical energy-bearing salts containing free cations and anions, zwitterionic energetic materials can be designed to integrate energy anions and cations into a single molecule.…”

“…The results show low mechanical sensitivity for compound 2 (IS >40 J, FS >360 N). Compared to other zwitterionic energetic materials such as 3-methyl-1,2,3-triazolium-1 N -dinitromethylylide (IS = 8 J, FS: 144–160 N), 14 its low mechanical sensitivity ensures safety during transportation. Compound 2 starts to decompose at 224 °C (Figure 5 ).…”

Synthesis and Energetic Characterization of Borane-Amines on High-Nitrogen Heterocycles

“…In contrast, zwitterionic N -oxides of high-nitrogen content heterocycles have been comparatively more widely investigated and shown to improve the properties of the parent energetic systems, with examples such as dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50), 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105), nitrotetrazole-2 N -oxide, and 3,6-diamino-1,2,4,5-tetrazine 1,4-dioxide (LAX-112) . In principle, N–BH 3 bonds may behave as zwitterions, which may yield a good comparison to N-oxides in energetic systems and possible related stabilization of such systems. − Accordingly, we have attempted the synthesis and characterization of various borane-amines of high-nitrogen content heterocycles and evaluated their hypergolicity with WFNA.…”