Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 48, Pages 14513-14517Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507456
Keywords
catenatednitrogenchains; energetic properties; explosives; nitroazoles
Categories
Funding
- ONR [NOOO14-12-1-0536]
- DTRA [HDTRA 1-11-1-0034]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1337908] Funding Source: National Science Foundation
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In the design of energetic materials, high energetic performance and good molecular stability are two main goals. Energetic functionalization which strives for maximum energy often results in unstable chemical bonds and causes safety problems in practical production and storage operations. In this work, N-nitro-and N-nitroamino-functionalized mono and bis(1,2,4-triazoles) were synthesized and characterized by infrared, and multinuclear NMR spectra, and elemental analyses. The N-nitroamino-functionalization strategy was employed for bis(imidazole), leading to high density compound 14 (2.007 gcm(-3) at 100 K; 1.94 gcm(-3) at room temperature) and energetic salt 15. While N-nitro-functionalized products are thermally unstable and highly moisture sensitive, N-nitroamino-functionalized energetic salts, which are comprised of additional nitrogen-containing ions, exhibit good density, moderate to excellent structural stabilities, and high performance.
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