Facile synthesis of thermally stable tetrazolo[1,5-<i>b</i>][1,2,4]triazine substituted energetic materials: synthesis and characterization

Kumar, Parasar; Ghule, Vikas D.; Dharavath, Srinivas

doi:10.1039/d2dt03814e

Cited by 14 publications

(10 citation statements)

References 32 publications

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“…The incorporation of various explosophoric groups such as nitro (-NO 2 ), nitramine (-NHNO 2 ), azide (-N 3 ), etc., on a particular heterocyclic framework is a widely used and effective strategy to boost the detonation performance of the compounds [19][20][21][22]. To address the ongoing demands for stable energetic materials with better performance, 1,2,3-triazoles, 1,3,5-triazines, pyrazoles, and imidazole have drawn much interest among other heterocyclic frameworks [23][24][25][26][27]. Energetic compounds with symmetric and asymmetric C-C bond combinations of heterocyclic backbones with five-membered rings are much explored in the literature [14,24], while the combination of six and five-membered C-C Abhishek Kumar Yadav and Manojkumar Jujam contributed equally.…”

Section: Introductionmentioning

confidence: 99%

Amine and nitramine functionalization of imidazole‐triazine and triazole‐triazine skeletons: Exploring for potential multipurpose energetic materials

Yadav,

Jujam,

Ghule

et al. 2023

Journal of Heterocyclic Chem

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A series of five and six‐membered C‐C bonded energetic materials (2–7) based on a combination of imidazole‐triazine and triazole‐triazine backbones were designed, synthesized, and characterized using NMR, IR, Mass spectrometry, and TGA‐DSC studies. Further, the structure of compound 4 was supported by single‐crystal X‐ray analysis. All the newly synthesized energetic compounds exhibit good density, excellent thermal stability, good detonation performance, and low mechanical sensitivity toward impact and friction. Among all, the nitrate salt 4 exhibits balanced properties, including high density (1.80 g cm−3), excellent thermal stability (254°C), good detonation velocity (8178 m s−1), and low sensitivity towards impact and friction. The facile synthetic feasibility, thermal stability, energetic performance, and insensitivity of all the molecules suggest they can be used as an insensitive secondary explosive in various defense and civilian applications.

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Section: Introductionmentioning

confidence: 99%

Amine and nitramine functionalization of imidazole‐triazine and triazole‐triazine skeletons: Exploring for potential multipurpose energetic materials

Yadav,

Jujam,

Ghule

et al. 2023

Journal of Heterocyclic Chem

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“…Energetic coordination polymers (ECPs), ,− energetic salts, ,− and energetic co-crystals , based on energetic parent molecules can overcome the various shortcomings of EMs such as their high friction or impact sensitivity, low energy, low density, and low thermal stability. Their energetic properties ( D v and P ) can also be modified and improved by combining them.…”

Section: Introductionmentioning

confidence: 99%

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

Zhang

Xiao

Dong

et al. 2023

Crystal Growth & Design

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A series of novel energetic materials (EMs) based on a single triazole−tetrazole material, (Z)-N-(5-nitro-2-(1Htetrazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)nitramide (HNANTT) with tremendous physicochemical (d = 1.833 g cm −3 and ΔH f = 715.8 kJ mol −1 ) and energetic properties (D v = 9209 m s −1 and P = 36.38 GPa), were obtained. Detailed crystal structures of HNANTT and NANTT-5, 7, 8, 9, 11, and 13 were determined by single-crystal X-ray diffraction. Based on HNANTT, three kinds of energetic coordination polymers (ECPs) (NANTT-5, 7, and 8), four energetic salts (NANTT-9, 10, 11, and 12), and one energetic cocrystal (NANTT-13) were prepared and characterized to develop EMs with different kinds of advantages. By modifying HNANTT, all NANTT derivatives (except NANTT-10) showed good mechanical sensitivity (IS > 40 J, FS > 360 N), with NANTT-ECP-8 achieving the highest density (2.729 g cm −3 ) and thermal stability (287 °C), NANTT-12 has the highest detonation performances (D v = 9225 m s −1 and P = 30.87 GPa) among NANTT materials, while the NANTT co-crystal of 13 exhibited the best comprehensive performance, with superior detonation properties (D v = 9035 m s −1 and P = 30.12 GPa), higher thermal stability (236 °C), and N + O content of 83.2%.

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“…8,9 However, the synthesis method of anions is also complex. 10,11 Hence, the energetic coordination compounds (ECCs), which combine the advantages of tunability, short synthesis period, and simplicity, are usually synthesized by choosing simple chain or heterocyclic compounds as ligands. This method has become increasingly popular in the development of energetic materials.…”

Section: Introductionmentioning

confidence: 99%

2-Imidazolidone metal complexes: increased hydrogen bonds and fused ring ligand ratio to be insensitive

Kuang,

Wang,

Zhang

et al. 2023

CrystEngComm

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Facile synthesis of thermally stable tetrazolo[1,5-b][1,2,4]triazine substituted energetic materials: synthesis and characterization

Abstract: Various thermally stable energetic materials with high nitrogen content, low sensitivity and better detonation performance were synthesized. The versatile functionalization of 1,2,4-triazine involving the introduction of oxadiazole and tetrazole is...

Cited by 14 publications

References 32 publications

Amine and nitramine functionalization of imidazole‐triazine and triazole‐triazine skeletons: Exploring for potential multipurpose energetic materials

Amine and nitramine functionalization of imidazole‐triazine and triazole‐triazine skeletons: Exploring for potential multipurpose energetic materials

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

2-Imidazolidone metal complexes: increased hydrogen bonds and fused ring ligand ratio to be insensitive

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