NDLI: Thermal stabilization of energetic materials by the aromatic nitrogen-rich 4,4′,5,5′-tetraamino-3,3′-bi-1,2,4-triazolium cation

Content Provider	Royal Society of Chemistry (RSC)
Author	Klapötke, Thomas M. Schnell, Simon Stierstorfer, Jörg Schmid, Philipp. C.
Copyright Year	2015
Abstract	4,4′,5,5′-Tetraamino-3,3′-bi-1,2,4-triazole (1) was prepared from readily available starting materials by a one-step procedure. Compound 1 consists of two combined aromatic triazole molecules with four amino moieties, resulting in a compound which has (i) high temperature stability, (ii) a high heat of formation, (iii) a high density and (iv) no sensitivity towards physical stimuli (friction, impact and electrostatic discharge). This compound has never previously been considered as a building block in the development of new energetic materials. We investigated compound 1 in detail as a potential nitrogen-rich, temperature-stable cation for the synthesis of energetic ionic derivatives (2–13) for use as environmentally benign explosives. The cation was combined with oxygen-rich counter-anions such as dinitramide (2), 5-nitrotetrazole-2-oxide (3), 5-nitrotetrazolate (4), nitrate (5), tetranitrobisimidazole (6), 5,5′-bitetrazole-1,1′-dioxide (7), 1,1′-dinitramino-5,5′-bitetrazolate (8), 5-nitriminotetrazolate (9), 1-methyl-5-nitriminotetrazolate (10), perchlorate (11), picrate (12) and nitroformate (13). Compounds 2–10 and 13 were characterized by low-temperature single-crystal X-ray diffraction. All the compounds were investigated by NMR and vibrational (IR, Raman) spectroscopy, mass spectrometry and elemental analysis. The excellent thermal properties of these compounds were determined by differential thermal analysis. The sensitivities towards impact, friction and electrical discharge were investigated using the BAM standards and a small-scale electrostatic discharge tester. The detonation parameters of the compounds without the inclusion of crystal water (1–3, 5–8, 11 and 13) were calculated using the EXPLO5 (V6.02) code and the calculated (CBS-4M) values for the enthalpy of formation.
Starting Page	2658
Ending Page	2668
Page Count	11
File Format	HTM / HTML PDF
ISSN	20507488
Volume Number	3
Issue Number	6
Journal	Journal of Materials Chemistry A
DOI	10.1039/c4ta05964f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Raman Triazole Electrostatic discharge Ion Nitrate Perchlorate Picric acid Trinitromethane X-ray crystallography Nuclear magnetic resonance spectroscopy Spectroscopy Mass spectrometry Differential thermal analysis CBS Standard enthalpy of formation
Content Type	Text
Resource Type	Article
Subject	Chemistry Renewable Energy, Sustainability and the Environment Materials Science

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