Evolving the Scope of 5,5’-Azobistetrazoles in the Search for High Performing Green Energetic Materials

Abstract

The azotetrazole moiety represents a great platform for energetic materials, it offers a planar and nitrogen-rich backbone, combined with a high heat of formation, which easily can be functionalized and tuned. Herein, we start from sodium 5-aminotetrazolate and obtain two isomers by substitution reaction with 2-chloroethanol. Azidoethyl and nitratoethyl substituted azo- tetrazoles were finally synthesized by oxidative azo coupling of the respective N-ethyl functionalized 5-aminotetrazole precursors using tert-butyl hypochlorite as reagent. All compounds were analyzed through multicore NMR and IR spectroscopy as well as mass spectrometry. All solid compounds were further investigated using low-temperature X-ray crystallography. The purity was verified by CHNO elemental analysis and the decomposition temperature (DTA) and sensitivities toward impact, friction and electrostatic discharged were determined. Based on the CBS-4M calculation results, the energetic properties were calculated using the EXPLO5 code.