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Energetic isomers of 1,2,4,5-tetrazine-bis-1,2,4-triazoles with low toxicity

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Abstract

A series of nitrogen-rich “green” Energetic Materials (EMs), some with improved sensitivity, thermostability, and very low toxicity, were synthesized on the basis of 3,5-diamino-1,2,4-triazole (DAT) and 1,2,4,5-tetrazine building blocks. Since DAT contains several nucleophilic reactive sites, obtaining selective reactivity and specific isomeric products with 1,2,4,5-tetrazine precursors is a challenging task. We developed reaction conditions under which specific isomers could be prepared. On evaluating these compounds for their energetic properties, we found that N5,N5′-(1,2,4,5-tetrazine-3,6-diyl)-bis(1H-1,2,4-triazole-3,5-diamine) 1 has very high thermostability (onset of decomposition temperature at 357 °C) and it is insensitive to impact (Im > 98 J), friction (>360 N) and electrostatic discharge (2512 mJ). A detonation velocity (Vod) of 8180 m s−1 was calculated for compound 1 and it was found to have extremely low toxicity in human cells (normal dermal fibroblasts) and in environmental bacteria (Vibrio fischeri). In combination with oxidants, compound 1 can generate 1225 L of gases (per kg of energetic mixture of an oxidant and compound 1), which makes this material a prospective component in solid propellants and a very good candidate for the development of solid state gas generators for clean fire-extinguishing systems and for a broad range of other civil and defense applications that require the use of “green” and insensitive EMs.

Graphical abstract: Energetic isomers of 1,2,4,5-tetrazine-bis-1,2,4-triazoles with low toxicity

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Publication details

The article was received on 15 Mar 2017, accepted on 04 Apr 2017 and first published on 04 Apr 2017


Article type: Paper
DOI: 10.1039/C7DT00935F
Citation: Dalton Trans., 2017, Advance Article
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    Energetic isomers of 1,2,4,5-tetrazine-bis-1,2,4-triazoles with low toxicity

    A. Shlomovich, T. Pechersky, A. Cohen, Q. L. Yan, M. Kosa, N. Petrutik, N. Tal, A. Aizikovich and M. Gozin, Dalton Trans., 2017, Advance Article , DOI: 10.1039/C7DT00935F

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