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Published on: February 7, 2017
Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent
Ping Yin1, Jiaheng Zhang2, Gregory H Imler3
1Department of Chemistry, University of Idaho, Moscow, ID, 83844-2343, USA.
Abstract:
A new fused N-heterocyclic framework, dipyrazolo-1,3,5-triazinane, was synthesized and the physiochemical properties of its derivatives were investigated to evaluate the integrated energetic performance. In contrast to 1,3,5-trinitro-1,3,5-triazinane (RDX) featuring a distorted chair confirmation, polynitro-functionalized dipyrazolo-1,3,5-triazinanes have nearly planar backbones, thereby enhancing the density and thermal stability. Among these new energetic tricyclic compounds, 5 a and 12 show favorable crystal densities of 1.937 g cm-3 and 1.990 g cm-3 at 150 K, respectively, which rank highest in triazinane-based energetic compounds. Additionally, this synthetic approach was carried out to form seven-membered and eight-membered rings, giving rise to tetranitro dipyrazolo-1,3,5-triazepane (5 b) and tetranitro dipyrazolo-1,3,5-triazocane (5 c), respectively.
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