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Klapötke, Thomas M.; Schmid, Philipp C.; Schnell, Simon; Stierstorfer, Jörg (25. November 2014): Thermal stabilization of energetic materials by the aromatic nitrogen-rich 4,4prime or minute{,}5{,}5prime or minute-tetraamino-3{,}3prime or minute-bi-1{,}2{,}4-triazolium cation. In: Journal of Materials Chemistry A, Vol. 3, Nr. 6: S. 2658-2668




4,4prime or minute{,}5{,}5prime or minute-Tetraamino-3{,}3prime or minute-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{,}5prime or minute-bitetrazole-1{,}1prime or minute-dioxide (7){,} 1{,}1prime or minute-dinitramino-5{,}5prime or minute-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.