4.7 Article

Syntheses, Structures, and Properties of Polynitro-Substituted 5,6-Dihydrodiimidazo[1,2-a:2′,1′-c]pyrazine Energetic Compounds

Journal

CRYSTAL GROWTH & DESIGN
Volume 22, Issue 6, Pages 3914-3923

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.cgd.2c00302

Keywords

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Funding

  1. National Natural Science Foundation of China [21975127, 22105102]
  2. Young Elite Scientist Sponsorship Program by CAST [YESS20210074]
  3. Fundamental Research Funds for the Central Universities [30921011204]

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A series of polynitro-substituted 5,6-dihydrodiimidazo[1,2-a:2',1'-c]pyrazine energetic compounds were synthesized by cyclization and nitration of biimidazole. The structures and properties of the compounds were investigated, and compounds 3-6 were found to be thermally stable and insensitive. They showed potential as replacements for TNT due to their superior detonation performances and good stabilities.
A series of polynitro-substituted 5,6-dihydrodiimidazo[1,2-a:2',1'-c]pyrazine energetic compounds were synthesized by cyclization and nitration of biimidazole. All newly synthesized compounds were fully characterized by infrared spectroscopy, H-1 and C-13 nuclear magnetic resonance spectroscopy, and elemental analysis. Single-crystal X-ray diffraction, iso-chemical shielding surfaces, localized orbital locator-pi, Hirshfeld surface analysis, and noncovalent interactions were employed to investigate the structures of 1-6. It is worth mentioning that compounds 3-6 are all thermally stable, with onset decomposition temperatures of 200-330 degrees C (DSC). Moreover, impact and friction sensitivity test results show that they are insensitive. Energy-related parameters, including densities, heats of formation, and detonation properties, were predicted according to the classical methods. In addition, the influence of the number and position of substituted nitro groups on density, heat of formation, and detonation performance was theoretically established. The superior detonation performances and good stabilities make compounds 4 and 5 useful as replacements for TNT.

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