Energetic compounds with fused tetracyclic backbones were synthesized and fully characterized, and their structures were confirmed by single crystal X-ray diffraction. Changes from nonplanar to planar structures led their densities to increase from 1.800 to 1.856 g cm-3 (298 K). Hydrogen bonds and π-π interactions were analyzed to understand this phenomenon. Energetic evaluations showed that compounds 2 and 3 detonated with performance comparable to TATB. Excellent mechanical sensitivities (IS: >40 J; FS: >360 N) indicate the promise of these furazans as insensitive energetic materials.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8ob02155d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
The synthesis and characterization of low-melting-point insensitive energetic materials are crucial due to their increasing applications in melt-cast explosives. In this work, a furazan-derived energetic compound, 3,4-bis[3(2-azidoethoxy)furazan-4-yl]furoxan (DAeTF), exhibiting insensitive and high-energy characteristics, is rationally designed and synthesized. The structure of DAeTF is characterized by nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, elemental analysis, mass spectrometry, and single-crystal X-ray diffraction.
View Article and Find Full Text PDFImprovement of Thermal Stability and Sensitivity of Furazan/Furoxan via Ring Closure Generation of Vicinal Amino-Nitro Structure.
J Org Chem
April 2024
School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.
Energetic compounds that display high thermal stability and insensitivity properties are essential for applications in mining, gas drilling, etc. In this work, a novel 4-nitro-5-aminoisoxazole energetic moiety oriented to enhance thermal stability and decrease the sensitivity of furazan/furoxan analogues was constructed. The generation of a vicinal amino-nitro structure can be effectively realized in one step by a green and mild ring-closing reaction of nitroacetonitrile potassium salt with chloroxime in aqueous solution.
View Article and Find Full Text PDFExpanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds.
J Org Chem
January 2024
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russian Federation.
A majority of known and newly synthesized energetic materials comprise polynitrogen or nitrogen-oxygen heterocycles with various explosophores. However, available structural combinations of these organic scaffolds are finite and are about to reach their limits. Herein, we present the design and synthesis of a series of sulfur-containing polyazole structures comprising 1,3,4-thiadiazole and furazan rings linked by C-C bonds and enriched with energetic nitro and azo functionalities.
View Article and Find Full Text PDFMethyl nitrate energetic compounds based on bicyclic scaffolds of furazan-isofurazan (isoxazole): syntheses, crystal structures and detonation performances.
RSC Adv
March 2022
College of Chemistry & Materials Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Northwest University Xi'an 710127 China
Two energetic bicyclic scaffolds (furazan-isoxazole and furazan-1,3,4-oxadiazole) were constructed different cyclization reactions. Based on the energetic bicyclic scaffolds, the energetic compounds, 3-(4-nitraminofurazan-3-ly)-isoxazole-5-methylnitrate 1c and 5-(4-nitraminofurazan-3-ly)-1,3,4-oxadiazole-2-methylnitrate 2c, were designed and synthesized in good yields. Because of the acidity of nitramine, the corresponding energetic ionic salts, ammonium 3-(4-nitraminofurazan-3-ly)isoxazole-5-methylnitrate 1d and ammonium 5-(4-nitraminofurazan-3-ly)-1,3,4-oxadiazole-2-methylnitrate 2e, were also obtained and well characterized, their structures were further determined by X-ray single crystal diffraction.
View Article and Find Full Text PDF1,3,4-Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level.
Angew Chem Int Ed Engl
March 2021
Department of Chemistry, University of Idaho, Moscow, ID, 83844-2343, USA.
Many energetic materials synthesized to date have limited applications because of low thermal and/or mechanical stability. This limitation can be overcome by introducing structural modifications such as a bridging group. In this study, a series of 1,3,4-oxadiazole-bridged furazans was prepared.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!