Impact of regiochemistry in energetic materials science: a case of (nitratomethyl-1,2,3-triazolyl)furazans

Epishina, Margarita A.; Ananyev, Ivan V.; Anisimov, Aleksei A.; Моногаров, Константин А.; Ферштат, Леонид Л.

doi:10.1039/d3dt00917c

Cited by 14 publications

(1 citation statement)

References 59 publications

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“…In this sense, 1,2,5-oxadiazole (furazan) attracts significant attention due to its high positive enthalpy of formation (216.9 kJ mol –1 ) and a substantial nitrogen–oxygen content presented within the core . Very recently, a series of furazan-based energetic assemblies incorporating diverse heterocyclic rings were prepared. − However, available structural combinations of nitrogen–oxygen heterocycles with various explosophores are finite and are about to reach their limits. Therefore, new synthetic strategies and conceptual findings are required to enrich the library of available energetic materials for various applications.…”

Section: Introductionmentioning

confidence: 99%

Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds

Deltsov,

Ananyev,

Meerov

et al. 2023

J. Org. Chem.

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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 sulfurcontaining polyazole structures comprising 1,3,4-thiadiazole and furazan rings linked by C−C bonds and enriched with energetic nitro and azo functionalities. In terms of detonation performance, all synthesized 1,3,4thiadiazole-furazan assemblies (D = 7.7−7.9 km s −1 ; P = 26−28 GPa) lie between the powerful explosive TATB (D = 8.0 km s −1 ; P = 31 GPa) and melt-cast material TNT (D = 6.9 km s −1 ; P = 23 GPa). In the synthesized series, azo-bridged derivative 5 seems to be most practically interesting, as it combines a relatively high energetic performance (D = 7.9 km s −1 ; P = 28 GPa), a very high thermal stability (271 °C), and insensitivity to friction. By these functional properties, 5 outperforms the benchmark heat-resistant explosive hexanitrostilbene (HNS). To the best of our knowledge, this is the first example of an energetic alliance of furazan and 1,3,4-thiadiazole scaffolds and a rare case of sulfur-containing high-energy materials, which can certainly be considered as an evolutionary step in energetic materials science.

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Section: Introductionmentioning

confidence: 99%

Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds

Deltsov,

Ananyev,

Meerov

et al. 2023

J. Org. Chem.

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Energetic Methylene‐Bridged Furoxan‐Triazole/Tetrazole Hybrids

Shaferov,

Ananyev,

Monogarov

et al. 2024

ChemPlusChem

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Design and synthesis of new energetic materials retains its urgency in chemistry and materials science. Herein, rational construction and regioselective synthesis of a series of energetic compounds comprising of a methylene‐bridged combination of 1,2,5‐oxadiazole and nitrogen‐rich azoles (1,2,4‐triazole and tetrazole) enriched with additional explosophoric functionalities (nitro and azo moieties) is presented. All target materials were thoroughly characterized using IR and multinuclear NMR (1H, 13C, 14N, 15N) NMR spectroscopy, high‐resolution mass spectrometry, X‐ray diffraction, and differential scanning calorimetry. All synthesized energetic substances showed good thermal stability (up to 239 °C) and low mechanical sensitivity, while their performance reached or exceeded the level of TNT.

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New energetic 1,2,4‐triazole‐nitrofuroxan hybrids

Larin,

Dubasova,

Ananyev

et al. 2024

Journal of Heterocyclic Chem

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New promising energetic materials comprised of 1,2,4‐triazole and furoxan rings and bearing explosophoric nitro group were rationally designed and synthesized. All newly prepared compounds were thoroughly characterized and their physicochemical properties were estimated. In the newly synthesized series, (1,2,4‐triazolyl)furoxan 4 is completely insensitive to impact and friction and possesses good detonation performance (D = 8.4 km s−1; P = 33 GPa) enabling its further exploration as a promising high‐energy material.

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Impact of regiochemistry in energetic materials science: a case of (nitratomethyl-1,2,3-triazolyl)furazans

Abstract: Preparation of multipurpose high-energy materials for space technologies remains a challenging task and such materials usually require special precautions and fine tunability of their functional properties. To unveil new opportunities...

Cited by 14 publications

References 59 publications

Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds

Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds

Energetic Methylene‐Bridged Furoxan‐Triazole/Tetrazole Hybrids

New energetic 1,2,4‐triazole‐nitrofuroxan hybrids

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