4.8 Article

3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 41, Pages 12895-12897

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606894

Keywords

detonation; energetic materials; fused heterocycle; N-functionalization; nitramines

Funding

  1. Office of Naval Research [N00014-16-1-2089]
  2. Defense Threat Reduction Agency [HDTRA 1-15-1-0028]
  3. CFD Research Corporation
  4. M. J. Murdock Charitable Trust [2014120:MNL:11/20/2014]
  5. Japan Society for the Promotion of Science (JSPS) [P15349]
  6. Grants-in-Aid for Scientific Research [15F15349] Funding Source: KAKEN

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A family of 3,6-dinitropyrazolo[4,3-c]pyrazole-based energetic compounds was synthesized by using versatile N-functionalization strategies. Subsequently, nine ionic derivatives of the N,N-(3,6-dinitropyrazolo[4,3-c]pyrazole-1,4-diyl)dinitramidate anion were prepared by acid-base reactions and fully characterized by infrared, multinuclear NMR spectra, and elemental analysis. The structures of four of these compounds were further confirmed by single-crystal X-ray diffraction. Based on their different physical and detonation properties, these compounds exhibit promising potential as modern energetic materials and can be variously classified as green primary explosives, high-performance secondary explosives, fuel-rich propellants, and propellant oxidizers.

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