Computational investigation and screening of [1,2,4]triazolo[4,3‐b][1,2,4,5]tetrazine‐based high energy materials

Liu, Luhao; Jin, Xinghui; Zhou, Junhu; Hu, Bingcheng

doi:10.1002/er.6161

Cited by 4 publications

(2 citation statements)

References 37 publications

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“…1,2,4,5-Tetrazine derivatives have been actively studied in recent years [19][20][21][22]. These compounds are attractive as highenergy materials [23][24][25], molecules with promising photophysical, electrochemical and coordination properties for use in sensors, OLEDs, semiconductor materials, etc. [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

Korotina¹,

Толщина²,

Ишметова³

et al. 2022

Beilstein J. Org. Chem.

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A series of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines has been synthesized through oxidation reaction of the corresponding 3,6-disubstituted 1,2,4,5-tetrazines bearing amidine fragments. It is shown that the heterocyclic systems obtained can be modified easily at C(3) position in the reactions with aliphatic alcohols and amines. Also, the reactivity of [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines towards CH-active compounds has been studied. The obtained triazolo[1,5-b]annulated 1,2,4,5-tetrazines proved to be active in micromolar concentrations in vitro against filamentous anthropophilic and zooanthropophilic dermatophyte fungi (Trichophyton, Microsporum and Epidermofiton), which cause skin and its appendages (hair, nails) diseases.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

Korotina¹,

Толщина²,

Ишметова³

et al. 2022

Beilstein J. Org. Chem.

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show abstract

“…These research results show that nitrogen-rich fused cyclic energetic materials with conjugated structures have aroused greater interest because of their high energy content and low mechanical sensitivity. [13][14][15][16][17] Besides, molecules with fused-ring always possess larger planar conjugate structures, more varieties of chemical modification sites, and more ring strain energy than those of single-ring skeletons, which in turn will enhance the energetic properties remarkably. [18,19] As a result, many potential HEDMs with fused di-tricyclic rings were synthesized and became to be as promising contenders to traditional energetic materials.…”

Section: Introductionmentioning

confidence: 99%

Assembling properties of 3,6‐dinitropyrazolo‐[4,3‐c]pyrazole‐based energetic compounds

Jin

Yuan

Shen

et al. 2022

J of Physical Organic Chem

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In pursuit of energetic materials with equal detonation properties and sensitivities compared to those of HMX and RDX, a series of 3,6-dinitropyrazolo-[4,3-c]pyrazole-based energetic compounds were designed, and density functional theory method was carried out to investigate the frontier molecular orbital, heats of formation, energetic properties, and impact sensitivities of the designed compounds. The results show that all the designed compounds possess high positive heats of formation range from 618.8 (A4) to 1934.3 kJ mol À1 (E2) and the -N 3 energetic group was the most effective unit to improve the values of heats of formation. Values of oxygen balance of compounds E8 and F8 were zero and possess the most ideal oxygen balance. The calculated detonation properties indicate that the -C (NO 2 ) 3 group was the most useful group to enhance the densities, detonation velocities, and detonation pressures.Nearly half of the designed compounds possess higher values of h 50 than RDX or HMX, which indicates that these compounds will be more stable than RDX and HMX. Based on detonation properties and impact sensitivities, five compounds (D3, D5, E5, F3, and F5) were screened as candidate compounds for high energy density materials. Finally, the distribution of the highest occupied molecular orbitals, the lowest unoccupied molecular orbitals, and electrostatic potential of the screened compounds were simulated to give an evident view on their physicochemical properties.

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Design and selection of pyrazolo[3,4-d][1,2,3]triazole-based high-energy materials

et al. 2021

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In this study, we design a series of bridged energetic compounds based on pyrazolo [3,4-d][1, 2, 3]triazole to screen potential energetic materials with excellent detonation properties and acceptable sensitivities. The electronic structures, heats of formation, detonation velocity, detonation pressure, and impact sensitivity of the designed compounds were calculated using density functional theory. The results showed that the designed compounds have high positive heats of formation in the range of 1035.4 (A7) to 2851.4 kJ mol −1 (D2). Moreover, the designed compounds have high crystal densities and heats of detonation, which signi cantly enhance detonation pressures and velocities. The detonation pressures and velocities are in the ranges of 6.23 (A1) to 9.65 km s −1 (D3) and 15.7 to 43.9 GPa (E8), respectively. The impact sensitivity data also suggest that the designed compounds have impact sensitivities in an acceptable range. Considering detonation pressures, detonation velocities, and impact sensitivities, six compounds (C3, C5, D3, D5, E3, and F3) were screened as potential materials with high energy density, excellent detonation properties, and low impact sensitivities. Finally, the electronic structures of the screened compounds were simulated to provide further understanding on the physicochemical properties of these compounds.

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Computational investigation and screening of [1,2,4]triazolo[4,3‐b][1,2,4,5]tetrazine‐based high energy materials

Cited by 4 publications

References 37 publications

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

Assembling properties of 3,6‐dinitropyrazolo‐[4,3‐c]pyrazole‐based energetic compounds

Design and selection of pyrazolo[3,4-d][1,2,3]triazole-based high-energy materials

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