Energetic heterocyclic N-oxides: synthesis and performance

Mendeleev Communications, Год журнала: 2022, Номер 32(6), С. 703 - 713

Опубликована: Ноя. 1, 2022

Язык: Английский

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

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 174 - 182

Опубликована: Дек. 11, 2023

A majority of known and newly synthesized energetic materials comprise polynitrogen or nitrogen–oxygen heterocycles with various explosophores. However, available structural combinations these organic scaffolds are finite about to reach their limits. Herein, we present the design synthesis a series sulfur-containing polyazole structures comprising 1,3,4-thiadiazole furazan rings linked by C–C bonds enriched nitro azo functionalities. In terms detonation performance, all 1,3,4-thiadiazole-furazan assemblies (D = 7.7–7.9 km s–1; P 26–28 GPa) lie between powerful explosive TATB 8.0 31 melt-cast material TNT 6.9 23 GPa). series, azo-bridged derivative 5 seems be most practically interesting, as it combines relatively high performance 7.9 28 GPa), very thermal stability (271 °C), insensitivity friction. By functional properties, outperforms benchmark heat-resistant hexanitrostilbene (HNS). To best our knowledge, this is first example an alliance rare case high-energy materials, which can certainly considered evolutionary step in science.

Язык: Английский

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

Dalton Transactions, Год журнала: 2023, Номер 52(22), С. 7673 - 7683

Опубликована: Янв. 1, 2023

The preparation of multipurpose high-energy materials for space technologies remains a challenging task and such usually require special precautions fine tunability their functional properties. To unveil new opportunities en route to high-performance energetic materials, novel potential melt-castable explosives plasticizers incorporating (1,2,3-triazolyl)furazan scaffold enriched with nitro nitratomethyl explosophoric functionalities were synthesized. successful implementation the regiodivergent approach enabled regioisomeric (nitratomethyltriazolyl)furazans that possessed significantly different physicochemical properties classifying target as substances or plasticizers. Hirshfeld surface calculations supported by energy framework plots also performed better understand relationship between molecular structure sensitivity. All prepared (1,2,3-triazolyl)furazans show high nitrogen-oxygen contents (76-77%), good experimental densities (up 1.72 g cm-3) positive enthalpies formation (180-318 kJ mol-1) resulting in detonation performances (D = 7.1-8.0 km s-1; P 21-29 GPa). Overall, this work unveils strategies construction balanced various applications.

Язык: Английский

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Nitrogen-rich tetracyclic-based heterocyclic energetic materials

Energetic Materials Frontiers, Год журнала: 2023, Номер 4(2), С. 110 - 122

Опубликована: Май 18, 2023

This review provides numerous studies on nitrogen-rich tetracyclic-based heterocyclic energetic materials including oxadiazole, tetrazole, triazole, pyrazole, imidazole and tetrazine. The article mainly describes the construction method of skeleton, explosive modification, properties tetracyclic materials. structure-property relationship was obtained by comparing a series Finally, authors summarize synthesis laws skeletons, which reference for development in future.

Язык: Английский

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Energetic 1,2,4-oxadiazoles: synthesis and properties

Russian Chemical Reviews, Год журнала: 2024, Номер 93(2), С. RCR5109 - RCR5109

Опубликована: Янв. 16, 2024

The study of high-energy materials based on poly nitrogen- and nitrogen-oxygen-containing heterocycles is one the most important relevant modern interdisciplinary research areas at intersection organic physical chemistry science. Among such heterocycles, 1,2,4-oxadiazole ring a rather interesting building block for synthesis new energetic compounds. Although 1,2,4-oxadiazoles has been developed more than 100 years, these have only recently become known are currently "hot spots" in this field This review systematizes published methods features reactivity 1,2,4-oxadiazole-based Mono- bis(1,2,4-oxadiazoles) as well structures containing other azoles pyrazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-triazole, 1,2,4-triazole tetrazole considered. For series structurally similar compounds, their physicochemical properties summarized factors affecting particular parameter discussed.<br> Bibliography — 123 references.

Язык: Английский

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Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

International Journal of Molecular Sciences, Год журнала: 2020, Номер 21(22), С. 8692 - 8692

Опубликована: Ноя. 18, 2020

Nowadays, an increasing number of heterocyclic-based drugs found application in medicinal chemistry and, particular, as anticancer agents. In this context, oxadiazoles—five-membered aromatic rings—emerged for their interesting biological properties. Modification oxadiazole scaffolds represents a valid strategy to increase activity, especially on 1,2,4 and 1,3,4 regioisomers. the last years, derivatives, with remarkable cytotoxicity several tumor lines, were identified. Structural modifications, that ensure higher towards malignant cells, represent solid starting point development novel oxadiazole-based drugs. To specificity strategy, outstanding have been designed selectively interact targets, including enzymes, globular proteins, nucleic acids, showing more promising antitumor effects. present work, we aim provide comprehensive overview activity these heterocycles, describing effect different targets highlighting how structural versatility has exploited modulate

Язык: Английский

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Novel energetic CNO oxidizer: Pernitro-substituted pyrazolyl-furazan framework

FirePhysChem, Год журнала: 2021, Номер 1(2), С. 83 - 89

Опубликована: Май 2, 2021

There is a need for dense energetic oxidizers whose composition restricted to carbon, hydrogen, nitrogen and oxygen atoms as chlorine-free alternative current of materials such explosives, propellants pyrotechnics. High heterocyclic frameworks containing trinitromethyl units are an attractive increasingly important class oxygen-rich compounds. Herein, the first time, synthetic method has been developed preparation new (pyrazole-3-yl)furazan framework bearing nitro group in furazan ring. From this framework, 3-nitro-4-(4-nitro-1-(trinitromethyl)-1H-pyrazol-3-yl)furazan (15) 3-(3,4-dinitro-1-(trinitromethyl)-1H-pyrazol-5-yl)-4-nitrofurazan (16) have produced. The combination positive enthalpy formation, high density, favorable physical thermal properties, reasonable sensitivity with promising theoretical performance these compounds offers not only fundamental interest, but also potential practical applications, example, candidates environmentally benign rocket propellants.

Язык: Английский

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

Chemistry - A European Journal, Год журнала: 2021, Номер 27(59), С. 14628 - 14637

Опубликована: Июль 29, 2021

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

Язык: Английский

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Power of sulfur – Chemistry, properties, laser ignition and theoretical studies of energetic perchlorate-free 1,3,4-thiadiazole nitramines

Chemical Engineering Journal, Год журнала: 2022, Номер 443, С. 136246 - 136246

Опубликована: Апрель 6, 2022

Язык: Английский

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Recent advances in the synthesis and performance of 1,2,4,5-tetrazine-based energetic materials

FirePhysChem, Год журнала: 2022, Номер 3(1), С. 78 - 87

Опубликована: Сен. 20, 2022

In recent years, the development of novel advanced energetic materials has significantly shifted toward nitrogen heterocyclic derivatives, which demonstrate a great potential for multipurpose application patterns. Among known heterocycles tetrazine ring is well-known structural scaffold used in preparation various high-energy materials. The majority energy-rich substances incorporating subunit exhibit high thermal stability, good detonation performance and low sensitivity to mechanical stimuli defines their practical usability. this review, main achievements on synthesis tetrazine-based reported last decade are summarized. Potential applications presented compounds especially emphasized.

Язык: Английский

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