4,4′-Bis(trinitromethyl)-3,3′-azo/azoxy-furazan: High-energy dense oxidizers

From Tetranitromethane to Gem-Dinitro-Bridged Nitrogen-Rich Heterocyclic Compound: Achieving High Heat of Detonation

“…Hydrogen-bonding interactions involving N···H and O···H of 3 , 4 , and 5 are 41.8, 47.1, and 59.3%, whereas the O···O interactions were found to be 30.2, 14.0, and 1.4%. According to previous studies, compounds with higher hydrogen-bonding interactions and lower O···O proportions usually are insensitive. − Thus, 4 and 5 are supposed to exhibit low sensitivities compared to 3 , which is in accord with our experimental results.…”

Synthesis of energetic salts based on 4-nitro-5-dinitromethyl-1,2,3-1H-triazole

“…The percentage of H⋯O&O⋯H and H⋯N&N⋯H in salts 8, 9 and 11 exceeds 60%, indicating the existence of a large number of hydrogen bonds in the crystal, which is also the reason why they have better thermal stability than potassium salts (6). 21 For energetic materials, the molecular electrostatic potential (ESP) obtained by Multiwfn has been widely used to interpret the relationship between impact sensitivity and molecular structure. 22 In the ESP, the blue area is electronegative, while the red area is electropositive.…”

Backbone Isomerization to Enhance Thermal Stability and Decrease Mechanical Sensitivities of 10 Nitro-Substituted Bipyrazoles

“…12−22 To date, several polynitro compounds have been synthesized, including 5,5′-bis(trinitromethyl)-3,3′-azo-1,2,4triazole, 9 2-dinitromethyl-5-nitrotetrazole, 13 1,3-bis-(trinitromethyl)-1,2,4-triazole, 15 5,5′-bis(trinitromethyl)-3,3′-bi(1,2,4-oxadiazole), 17 bis(2-difluoramino-2,2-dinitroethyl)nitramine, 23 and 4,4′-bis (trinitromethyl)-3,3′-azo/azoxy-furazan. 24 Polynitro compounds bearing trinitromethyl moieties are the most promising high-energy density oxidizers. However, owing to the existence of numerous nitro groups in molecules, polynitro compounds always have poor thermostability and mechanical sensitivity, limiting their practical applicability.…”

“…Introducing sufficient oxygen-containing groups (e.g., hydroxyl, nitro, dinitromethyl, and trinitromethyl) at the energetic skeleton modification site is the most direct and effective technique to improve the oxygen balance of a compound (Figure a). − Oxygen-containing groups, such as trinitromethyl, not only improve the nitrogen–oxygen content and energy but also allow the introduction of several nitro groups at a single modification site. Several methods have been developed for introducing trinitromethyl groups into heterocyclic compounds, including the use of trinitroethyl building blocks and direct nitration with ethyl acetate, acetonyl, or nitrile. − To date, several polynitro compounds have been synthesized, including 5,5′-bis­(trinitromethyl)-3,3′-azo-1,2,4-triazole, 2-dinitromethyl-5-nitrotetrazole, 1,3-bis­(trinitromethyl)-1,2,4-triazole, 5,5′-bis­(trinitromethyl)-3,3′-bi­(1,2,4-oxadiazole), bis­(2-difluoramino-2,2-dinitroethyl)­nitramine, and 4,4′-bis (trinitromethyl)-3,3′-azo/azoxy-furazan . Polynitro compounds bearing trinitromethyl moieties are the most promising high-energy density oxidizers.…”