Synthesis and Characterization of Pyrazole‐Triazolone Compound with Exceptional Heat Resistance DOI
Han Zhang, Lu Zhang,

Qamar‐un‐Nisa Tariq

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(4)

Published: Jan. 22, 2024

Abstract Efficiently constructing structures with high thermal stability is a key objective in the development of energetic compounds. However, existing synthesis processes for heat‐resistant materials are frequently hampered by their complexity and low yields. This study presents significant breakthrough addressing these challenges. It successfully synthesizes 4‐amino‐5‐(3‐amino‐1 H ‐pyrazole‐4‐yl)‐2,4‐dihydro‐3 ‐1,2,4‐triazol‐3‐one (APTO) using streamlined two‐step process, achieving an impressive yield 87.5 %. The structure was determined through X‐ray single crystal diffraction analysis, revealing nearly planar intramolecular structure. Hirshfeld surface weak interaction aromaticity analysis were conducted, illustrating substantial presence hydrogen bonds π ‐ stacking interactions within between molecules. These contribute significantly to exceptional ATPO. Furthermore, ATPO confirmed DSC exhibiting decomposition temperature as 365.2°C. surpasses that explosive HNS (325°C), further validating its excellent stability. construction this conjugated offers valuable guidance future structural design materials. opens up possibilities novel compounds improved based on similar architectures.

Language: Английский

2,2′-Azobis(1,5′-bitetrazole) with a N10 Chain and 1,5′-Bitetrazolate-2N-oxides: Construction of Highly Energetic Nitrogen-Rich Materials Based on C–N-Linked Tetrazoles DOI
Ze Xu,

Tianyang Hou,

Feng Yang

et al.

ACS Applied Materials & Interfaces, Journal Year: 2023, Volume and Issue: 15(35), P. 41580 - 41589

Published: Aug. 23, 2023

A series of high-nitrogen compounds, including a unique molecule 2,2'-azobis(1,5'-bitetrazole) with branched N10 chain and 1,5'-bitetrazolate-2N-oxides, were synthesized successfully based on C-N-linked 1,5'-bistetrazoles using azo coupling N-amine bonds N-oxide introduction strategies. All compounds characterized by NMR spectroscopy, IR elemental analysis, differential scanning calorimetry, in which the structures five further determined single-crystal X-ray diffraction analysis (2, T-N10B, 3a, 3b, THX). The nitrogen contents these range from 63.62 (THX) to 83.43% (T-N10B), are much higher than that CL-20 (38.34%). heat formation for prepared was calculated Gaussian 09 program, T-N10B having highest value 5.13 kJ g-1, about 6 times (0.83 g-1). detonation performances EXPLO5 v6.05.04 show THX has excellent performance (D = 9581 m s-1, P 35.93 GPa) remarkable specific impulse (Isp 284.9 s).

Language: Английский

Citations

24
A zwitterionic fused-ring framework as a new platform for heat-resistant energetic materials DOI

Ruibing Lv,

Lan Jiang, Jinxin Wang

et al.

Journal of Materials Chemistry A, Journal Year: 2024, Volume and Issue: 12(17), P. 10050 - 10058

Published: Jan. 1, 2024

A zwitterionic fused-ring based energetic material (ZDPT) was prepared. ZDPT has excellent thermal stability ( T d = 347 °C ) and great detonation velocity D 8390 m s −1 ), which endow with potential as a heat-resistant material.

Language: Английский

Citations

16
Combination of Tetrazole and 4-Azido-pyrazolotriazine Oxide: Balance of High Nitrogen, Energy, and Safety DOI

Hanghong Fan,

Jie Tang, Wei Hu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

Energetic materials containing a pyrazolotriazine oxide skeleton have the potential for high performance. However, research on is very limited due to inherent ring system instability and synthetic approaches. In this paper, APTO OPTO with combination of high-nitrogen tetrazole promising azido-pyrazolotriazine been synthesized. Of these, its energetic salts exhibit excellent detonation properties (Dv > 8220 m s–1; P 26.50 GPa). Surprisingly, exhibits performance = 8913 32.43 GPa) comparable that RDX.

Language: Английский

Citations

1
Achieving Ultra-High Heat Resistance of Novel Energetic Materials through Hydrogen Bonding and Extended π-Conjugation Strategy DOI
Xiue Jiang,

Dangyue Yin,

Siwei Song

et al.

Journal of Materials Chemistry A, Journal Year: 2024, Volume and Issue: 12(22), P. 13231 - 13239

Published: Jan. 1, 2024

Two high-performance heat-resistant energetic materials were developed via a synergistic strategy of designing hydrogen bonding networks and expanding the π-conjugation system.

Language: Английский

Citations

9
Construction of a series of insensitive energetic materials starting from the condensation reaction of 3-amino-4-cyanofurazan DOI
Yuangang Xu, Lujia Ding, Dongxue Li

et al.

Journal of Materials Chemistry A, Journal Year: 2024, Volume and Issue: 12(28), P. 17714 - 17729

Published: Jan. 1, 2024

A library of energetic materials synthesized from 3-amino-4-cyanofurazan has been disclosed, in which compound 7 is a unique example an with fluorescence, opens the door for many new applications.

Language: Английский

Citations

6
Approaching the Thermostability Limit of Nitrogen-Rich Heterocyclic Perchlorate-Based Energetic Materials DOI

Xiue Jiang,

Dangyue Yin,

Mingren Fan

et al.

ACS Applied Materials & Interfaces, Journal Year: 2024, Volume and Issue: 16(37), P. 49434 - 49441

Published: Sept. 4, 2024

In recent years, driven by ever-increasing application of energetic materials in deep-seated mineral resource exploitation and aerospace engineering, the mining advanced safe with significant thermal stability has drawn widespread publicity. Here, a tricyclic bridged compound 2-amino-4,6-bis(3,5-diamino-4-nitropyrazol-1-yl)-1,3,5-triazine (

Language: Английский

Citations

5
Energetic Gem-dinitro Salts with Improved Thermal Stability by Incorporating with A Fused Building Block DOI
Xun Zhang, Yaxi Wang, Yubing Liu

et al.

ACS Applied Materials & Interfaces, Journal Year: 2022, Volume and Issue: 14(33), P. 37975 - 37981

Published: Aug. 11, 2022

Thermal stability is one of the most significant properties for safety energetic materials, finding a stable skeleton with suitable groups always primary test. In this work, an unusual aminohydrazone cyclization strategy was used in synthesis new series gem-dinitro 1,2,4-triazolo[4,3-b][1,2,4,5]-tetrazine compounds desirable thermal (≥197 °C). All were fully characterized by infrared (IR), NMR, differential scanning calorimetry, single crystal X-ray diffraction, and elemental analysis. The decomposition temperature potassium salt 2 288 °C, reaching level HMX. these performances have demonstrated effective innovatively combining geminal dinitro fused rings.

Language: Английский

Citations

19
Synthesis and reactivity of 5-hydrazino-3-nitro-1,2,4-triazole (HNT): an amphoteric energetic platform DOI

Loïc Habert,

Matthieu Daniel, P. Palmas

et al.

Journal of Materials Chemistry A, Journal Year: 2023, Volume and Issue: 11(25), P. 13564 - 13569

Published: Jan. 1, 2023

Here is described the first synthesis of 5-hydrazino-3-nitro-1,2,4-triazole (HNT), as a free base, from 5-bromo-3-nitro-1,2,4-triazole (BNT) in three steps.

Language: Английский

Citations

11
From Concept to Synthesis: Developing Heat-Resistant High Explosives through Automated High-Throughput Virtual Screening DOI
Zujia Lu, Yong Hu,

Wen‐Shuai Dong

et al.

The Journal of Physical Chemistry C, Journal Year: 2023, Volume and Issue: 127(38), P. 18832 - 18842

Published: Sept. 14, 2023

In this paper, we investigate the utilization of high-throughput virtual screening (HTVS) to identify and develop novel heat-resistant high explosives (HRHEs) that possess a decomposition temperature exceeding 300 °C detonation velocity surpassing 8000 m·s–1. To achieve this, constructed molecular library composed pyrimidine as parent ring various five-membered heterocycles guest rings connected by an amino bridge. The GFN-xTB method, extended tight binding is employed facilitate geometry optimization vibrational analysis, thereby enabling application more precise versatile quantum chemical calculation in HTVS workflow. Our efforts resulted synthesis three compounds exhibited remarkable stability with temperatures 320 °C, suggesting their potential HRHEs. Notably, compound K19-21 demonstrated 324.6 8293 m·s–1, both 2,2′,4,4′,6,6′-hexanitrostilbene (HNS) 2,6-bis(picrylamino)-3,5-dinitropyridine (PYX) rivaling l,3,5-triamino-2,4,6-trinitrobenzene (TATB). These results support efficacy our design concepts Overall, study underscores importance accelerating discovery new materials possessing desired properties, especially field energetic materials.

Language: Английский

Citations

11
Regulating the Thermal Stability and Energy of Fused-Ring Energetic Materials by Hydrazo Bridging and Hydrogen-Bonding Networks DOI
Sitong Chen, Lu Li, Siwei Song

et al.

Crystal Growth & Design, Journal Year: 2023, Volume and Issue: 23(7), P. 4970 - 4978

Published: June 2, 2023

In this work, a combined strategy of bridging two tetrazolo[1,5-b]pyridazine rings and introducing intramolecular hydrogen bonds (N–H···O) with hydrazo group was developed to construct new high-energy heat-resistant energetic compound named 6,6′-hydrazo-bis(8-amino-7-nitrotetrazolo[1,5-b]pyridazine) (1). Its dehydrogenated derivative 6,6′-azo-bis(8-amino-7-nitrotetrazolo[1,5-b]pyridazine) (2), which had fewer (N–H···O), also synthesized for comparison. Compounds 1 2 were characterized by high-resolution mass spectrometry, nuclear magnetic resonance, single-crystal X-ray diffraction, infrared spectroscopy, elemental analysis. Their properties, such as densities (ρ: 1.87 g·cm–3 1, 1.77 2), heat formation values (ΔHf: 1079 kJ·mol–1 1235 detonation velocities (Dv: 9064 m·s–1 8429 pressures (P: 35.2 GPa 27.8 decomposition temperatures (Td: 292 °C 260 impact sensitivities (IS: 16 J 4 friction (FS: >360 N 160 tested. These results suggest that is promising thermally stable material.

Language: Английский

Citations

10