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Mayr, Norbert (2013): Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives: synthesis and characterization. Dissertation, LMU München: Faculty of Chemistry and Pharmacy



The synthesis and properties of explosive urea and triazine derivatives is investigated on behalf of the explosive parameters and the full characterization of the molecules. (Chapter I-III) The class of oxadiazole derivatives is enhanced from the known explosive 1,2,5 oxadiazole (furazane) derivatives to the 1,2,4 oxadiazole derivatives. This molecule class is thoroughly investigated by all terms of chemical and explosive material matter and especially the 1,2,4-oxadiazol-5-one derivatives are compared to the corresponding tetrazole derivatives which were by far the most investigated molecule moiety of Prof. Dr. T.M. Klapoetke et al. for more than the last ten years. The 1,2,4 oxadiazol-5-one derivatives do only value as comparable model molecule to the tetrazole but were found to be good explosives themselves. So the triaminoguanidinium 1,2,4-oxadiazol-5-onate is suitable as low temperature propellant, the potassium and cesium 1,2,4-oxadiazol-5-onate are found to be good additions for NIR-flares and last but not least the best performing molecule was found to be the 3,5-diamino-1,2,4-oxadiazolium 5-aminotetrazolate, which combines the stability of the oxadiazole moiety with the very exothermic properties of a tetrazole in its best way. (Chapter IV-V) The 3-amino-1,2,4(4H)-oxadiazol-5-one is investigated thoroughly and detected to be a chemically and thermodynamically more stable system which can be functionalized according to methods known prior in the working group. The 3-dinitromethyl-1,2,4(4H)-oxadiazol-5-one is found a promising explosive class which can be combined as anion with a wide range of cations to tailor the stability and performance. The overall conclusion is that the 1,2,4-oxadiazole are chemical suitable as well as secondary explosives, propellants and pyrotechnics.