Chemistry - A European Journal, volume 27, issue 59, pages 14628-14637

Design and Synthesis of Nitrogen-Rich Azo-Bridged Furoxanylazoles as High-Performance Energetic Materials

Publication typeJournal Article
Publication date2021-09-29
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor4.3
ISSN09476539, 15213765
General Chemistry
Catalysis
Organic Chemistry
Abstract

A series of novel energetic materials comprising of azo‐bridged furoxanylazoles enriched with energetic functionalities was designed and synthesized. These high‐energy materials were thoroughly characterized by IR and multinuclear NMR (1H, 13C, 14N) spectroscopy, high‐resolution mass spectrometry, elemental analysis, and differential scanning calorimetry (DSC). The molecular structures of representative amino and azo oxadiazole assemblies were additionally confirmed by single‐crystal X‐ray diffraction and X‐ray powder diffraction. A comparison of contributions of explosophoric moieties into the density of energetic materials revealed that furoxan and 1,2,4‐oxadiazole rings are the densest motifs while the substitution of the azide and amino fragments on the nitro and azo ones leads to an increase of the density. Azo bridged energetic materials have high nitrogen‐oxygen contents (68.8–76.9 %) and high thermal stability. The synthesized compounds exhibit good experimental densities (1.62–1.88 g cm−3), very high enthalpies of formation (846–1720 kJ mol−1), and, as a result, excellent detonation performance (detonation velocities 7.66–9.09 km s−1 and detonation pressures 25.0–37.7 GPa). From the application perspective, the detonation parameters of azo oxadiazole assemblies exceed those of the benchmark explosive RDX, while a combination of high detonation performance and acceptable friction sensitivity of azo(1,2,4‐triazolylfuroxan) make it a promising potential alternative to PETN.

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Larin A. A. et al. Design and Synthesis of Nitrogen-Rich Azo-Bridged Furoxanylazoles as High-Performance Energetic Materials // Chemistry - A European Journal. 2021. Vol. 27. No. 59. pp. 14628-14637.
GOST all authors (up to 50) Copy
Larin A. A., Shaferov A. V., Kulikov A., Pivkina A., Monogarov K., Dmitrienko A. O., Ananyev I. V., Khakimov D., Fershtat L. L., Makhova N. N. Design and Synthesis of Nitrogen-Rich Azo-Bridged Furoxanylazoles as High-Performance Energetic Materials // Chemistry - A European Journal. 2021. Vol. 27. No. 59. pp. 14628-14637.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/chem.202101987
UR - https://doi.org/10.1002%2Fchem.202101987
TI - Design and Synthesis of Nitrogen-Rich Azo-Bridged Furoxanylazoles as High-Performance Energetic Materials
T2 - Chemistry - A European Journal
AU - Shaferov, Alexander V
AU - Fershtat, Leonid L.
AU - Larin, Alexander A
AU - Kulikov, Alexander
AU - Pivkina, Alla
AU - Monogarov, Konstantin
AU - Dmitrienko, Artem O.
AU - Ananyev, Ivan V
AU - Khakimov, Dmitry
AU - Makhova, Nina N.
PY - 2021
DA - 2021/09/29 00:00:00
PB - Wiley
SP - 14628-14637
IS - 59
VL - 27
SN - 0947-6539
SN - 1521-3765
ER -
BibTex |
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BibTex Copy
@article{2021_Larin,
author = {Alexander V Shaferov and Leonid L. Fershtat and Alexander A Larin and Alexander Kulikov and Alla Pivkina and Konstantin Monogarov and Artem O. Dmitrienko and Ivan V Ananyev and Dmitry Khakimov and Nina N. Makhova},
title = {Design and Synthesis of Nitrogen-Rich Azo-Bridged Furoxanylazoles as High-Performance Energetic Materials},
journal = {Chemistry - A European Journal},
year = {2021},
volume = {27},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002%2Fchem.202101987},
number = {59},
pages = {14628--14637},
doi = {10.1002/chem.202101987}
}
MLA
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MLA Copy
Larin, Alexander A., et al. “Design and Synthesis of Nitrogen-Rich Azo-Bridged Furoxanylazoles as High-Performance Energetic Materials.” Chemistry - A European Journal, vol. 27, no. 59, Sep. 2021, pp. 14628-14637. https://doi.org/10.1002%2Fchem.202101987.
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