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Issue 13, 2019
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Multipurpose [1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine-based energetic materials

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Two series of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine-based energetic materials were synthesized effectively by using monosubstituted tetrazine or tetrazine-based fused rings as starting materials. Among them, compound 5 exhibits excellent insensitivity toward external stimuli (IS = 43 J and FS > 360 N) and a very good calculated detonation performance (Dv = 9408 m s−1 and P = 37.8 GPa) that are comparable to the current secondary-explosive benchmark, CL-20, which strongly suggests 5 as a secondary explosive. The azo compound 10 has a remarkable measured density of 1.91 g cm−3 at 20 °C, excellent thermal stability (Td = 305 °C), and very good calculated detonation performance (Dv = 9200 m s−1 and P = 34.8 GPa), which outperforms all current heat-resistant explosives. Compound 10 has a significant potential as a heat-resistant explosive. Compounds 14, 17 and 19 are very sensitive (IS ≤ 2 J and FS ≤ 100 J) but exhibit excellent calculated detonation performance (Dv ≥ 8690 m s−1 and P ≥ 30.2 GPa) which are very high values among current azide-containing primary explosives. These attractive features suggest strong possibilities for applications as primary explosives. A detailed study based on X-ray diffraction is used to illustrate the relationship between weak interactions and sensitivity of energetic materials. Attempts were made to design next-generation fused ring energetic materials for different applications as an alternating kind or site of the substituent group(s).

Graphical abstract: Multipurpose [1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine-based energetic materials

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14 Feb 2019
08 Mar 2019
First published
08 Mar 2019

J. Mater. Chem. A, 2019,7, 7875-7884
Article type
Author version available

Multipurpose [1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine-based energetic materials

Y. Liu, G. Zhao, Y. Tang, J. Zhang, L. Hu, G. H. Imler, D. A. Parrish and J. M. Shreeve, J. Mater. Chem. A, 2019, 7, 7875
DOI: 10.1039/C9TA01717H

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