Fused heterocycle-based energetic materials (2012–2019)

Gao, Haixiang; Zhang, Qinghua; Shreeve, Jean’ne M.

doi:10.1039/c9ta12704f

Cited by 308 publications

(180 citation statements)

References 56 publications

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“…6,23 Heterocycles constitute one of the widely studied classes of organic compounds as they are key to the structural units in various biologically and medicinally-important natural and synthetic products. [24][25][26] Moreover, importance of heterocyclic compounds in material science 27,28 and pharmaceutical 29 applications led their preparation and functionalization as topic of interest in organic synthesis. Owing to their wide scale importance, several researchers have devoted their studies in developing novel methodologies to access oxygen-, nitrogenand sulphur-containing heterocyclic scaffolds.…”

Section: Introductionmentioning

confidence: 99%

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

Shetgaonkar¹,

Singh²

2021

Arkivoc

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Hypervalent iodine chemistry has witnessed exponential growth in organic synthesis in recent times. Because of the electrophilic and good-leaving nature of hypervalent iodine reagents, they react with different nucleophiles in various synthetic transformations such as rearrangements, α-functionalization of carbonyl compounds, alkene difunctionalization and oxidation reactions. Importantly, the application of hypervalent iodine reagents in the construction of heterocycles is of great interest and has been well studied over the years. This review article highlights the recent developments accomplished by hypervalent iodine reagents in the synthesis and functionalization of heterocyclic compounds.

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Section: Introductionmentioning

confidence: 99%

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

Shetgaonkar¹,

Singh²

2021

Arkivoc

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“…As a significant material for the development of the economy and weapons industry, energetic materials used in both military and civilian fields have gained global interest over the past few decades [1][2][3]. However, traditional energetic compounds, such as trinitrotoluene (TNT) [4][5][6], hexogen (RDX), octogen (HMX) [7][8][9], and hexanitrohexaazaisowurtzitane (CL-20) [10][11][12], cannot meet the requirements of the rapidly developing military and space industry; furthermore, some of these compounds are still faced with several issues, such as high cost [13], high toxicity [14,15], and contamination [16].…”

Section: Introductionmentioning

confidence: 99%

Review on the Synthesis and Performance for 1,3,4‐Oxadiazole‐Based Energetic Materials

Wang

et al. 2021

Propellants Explo Pyrotec

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Energetic materials have been widely used in both military and civilian fields. The development of new high-energy materials with improved performance and enhanced stability is critical for promoting future military and space applications. Recently, researchers in the field of energetic materials have paid significant attention to oxadiazole-based energetic compounds, among which 1,3,4oxadiazole demonstrates moderate energy levels and better stability, owing to the absence of readily cleaved NÀ O bonds compared with other oxadiazole isomers, such as 1,2,4-oxadiazole and 1,2,5-oxadiazole. Therefore, 1,3,4-oxadiazole is an exceptional explosophoric motif with an efficient compromise between energy and stability, and several outstanding energetic materials have been achieved based on the combination of 1,3,4-oxadiazole units with various functional groups or rings, such as polynitrobenzene, furazan, pyrazole, and 1,3,4-oxadiazole itself. This review provides an overview of the development of 1,3,4-oxadiazole-based energetic materials during the past few years, outlines their synthesis and energetic performance, and contrasts them with other conventional energetic materials. Owing to the convenience of the synthetic routes and their excellent energetic properties, energetic materials based on the 1,3,4-oxadiazole skeleton may be considered as the next-generation of high-performance energetic materials specifically as heat-resistant explosives or insensitive explosives.

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“…However, the insufficiency of nitrogen atoms in the above‐mentioned materials lead to the low energy output for energetic devices [2]. Additionally, the correlation between N‐heterocyclic skeleton and thermal stability as well as energy density has not been thoroughly referred [3–5]. Over the past few years, a series of thermally‐stable heterocyclic organic explosives emerged in large numbers, such as 1,3,4‐oxadiazole bridged trinitrophenyl derivatives [6], fused triazolo‐tetrazine [7], furazano[3,4‐b]pyrazine [8], bridging nitropyrazole derivatives with 1,3,4‐oxadiazole [9], 1,2,4‐oxadiazole [10], 1,2,5‐oxadiazole [11], 5,6‐fused bicycles [12], combination of 1,2,4‐oxadiazole derivatives with 1,2,5‐oxadiazole [13], polyaminotriazole derivatives and energetic salts [14–16], fused heterocyclic derivatives [17], etc.…”

Section: Introductionmentioning

confidence: 99%

Heat‐Resistant Energetic Materials Deriving from Benzopyridotetraazapentalene: Halogen Bonding Effects on the Outcome of Crystal Structure, Thermal Stability and Sensitivity

Zhang

Geng

Yang

et al. 2021

Propellants Explo Pyrotec

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Heat‐resistant energetic material (HREM) has shown its broad applications in petroleum and natural gas exploration, aerospace vehicle as well as solid rocket formulations. Benzopyridotetraazapentalene (BPTAP) (d: 1.84 g cm−3, D: 7670 m s−1, IS: 9 J, Td: 366 °C) is a heat‐resistant energetic material, which is more dense and energetic than those of commercial HREM hexanitrosilbene (HNS) (d: 1.74 g cm−3, D: 7612 m s−1, IS: 5 J, Td: 318 °C). However, low solubility in most of commonly‐used solvents has restricted its applications in detonators as nano‐energetic materials. Meanwhile, recognition on this fused organic backbone is still limited. Herein, we report a chlorine‐inclusion strategy and facile approaches to yield three new derivatives of BPTAP. It is notable that compound 6‐a exhibits its high density (1.92 g cm−3), superior thermal stability (Td: 334 °C), high detonation performance (D: 8084 m s−1), comparable sensitivity (IS: 3 J) to that of HNS, surpassing those of commercially‐used highly‐sensitive primary energetic material lead azide (LA). It is interesting that the chlorine‐inclusion in different position of fused benzopyridotetraazapentalene framework has greatly affected their physical properties such as crystal structure, thermal stability and sensitivity. This investigation offers a unique perspective for deeply exploring the relationship between structure and performance of energetic materials.

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Fused heterocycle-based energetic materials (2012–2019)

Abstract: Fused heterocycles are unique building blocks for the synthesis of a wide range of high-performance energetic materials.

Cited by 308 publications

References 56 publications

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

Review on the Synthesis and Performance for 1,3,4‐Oxadiazole‐Based Energetic Materials

Heat‐Resistant Energetic Materials Deriving from Benzopyridotetraazapentalene: Halogen Bonding Effects on the Outcome of Crystal Structure, Thermal Stability and Sensitivity

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