Energetic N -azidomethyl derivatives of polynitro hexaazaisowurtzitanes series: CL-20 analogues having the highest enthalpy

High endothermicity is one of the most important factors in the design of high-performance energetic materials for a new generation of rocket technologies. Taking this into account, in this study, novel highly energetic cage compounds were synthesized by the incorporation of a high-enthalpy N -azido...

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Bibliographic Details
Published in:New journal of chemistry 2020-05, Vol.44 (20), p.8357-8365
Main Authors: Luk′yanov, Oleg A., Parakhin, Vladimir V., Shlykova, Nina I., Dmitrienko, Artem O., Melnikova, Elizaveta K., Kon'kova, Tatyana S., Monogarov, Konstantin A., Meerov, Dmitry B.
Format: Article
Language:English
Subjects:
Cage compounds
Crystallography
Density
Derivatives
Design factors
Energetic materials
Enthalpy
Heat resistance
Infrared spectroscopy
Mass spectrometry
Nitrogen isotopes
NMR
Nuclear magnetic resonance
Spacecraft components
Synthesis
Thermal resistance
Thermal stability
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Summary:High endothermicity is one of the most important factors in the design of high-performance energetic materials for a new generation of rocket technologies. Taking this into account, in this study, novel highly energetic cage compounds were synthesized by the incorporation of a high-enthalpy N -azidomethyl moiety into the polynitro hexaazaisowurtzitane backbone. All obtained compounds were fully characterized by high-resolution mass spectrometry, IR and multinuclear NMR ( 1 H, 13 C, 14 N, 15 N) spectroscopy. For two of them, 4-azidomethyl-2,6,8,10,12-pentanitrohexaazaisowurtzitane and 4,10-bis(azidomethyl)-2,6,8,12-tetranitrohexaazaisowurtzitane, the density and structural features were established by X-ray diffractometry. Enthalpies of formation were determined experimentally by combustion calorimetry. Thermal stability measurements and testing of impact and friction sensitivity were also carried out. The synthesized compounds exhibit a high level of heat resistance (decomposition onset 180–205 °C) and density (1.85–1.93 g cm −3 ). Their enthalpies of formation on a unit of mass (up to 2210 kJ kg −1 ) are the highest among the known hexaazaisowurtzitane derivatives and are 2–2.5 times that of CL-20. The combination of these attractive properties makes the new materials promising energetic components for propellant compositions.
ISSN:1144-0546
1369-9261
DOI:10.1039/D0NJ01453B