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Evolving the Scope of 5,5’‐Azobistetrazoles in the Search for High Performing Green Energetic Materials
Author(s) -
Benz Maximilian,
Gruhne Michael S.,
Klapötke Thomas M.,
Krüger Nina,
Lenz Tobias,
Lommel Marcus,
Stierstorfer Jörg
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100747
Subject(s) - chemistry , moiety , reagent , elemental analysis , mass spectrometry , decomposition , sodium hypochlorite , combinatorial chemistry , inorganic chemistry , organic chemistry , chromatography
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.