Issue 20, 2021

Tunable Dimroth rearrangement of versatile 1,2,3-triazoles towards high-performance energetic materials

Abstract

A highly efficient strategy of two different types of nitrogen-rich heterocyclic energetic compounds, featuring a single NH-bridge (–NH–) and a fused ring, was demonstrated by virtue of Dimroth rearrangement reactions using 4-amino-5-nitro-1,2,3-triazole as the precursor. Various nitrogen-rich compounds and their salts were prepared via this transformation and fully characterized using multinuclear NMR spectroscopy, IR, elemental analysis, and single crystal X-ray structuring. Their key properties, such as decomposition temperatures, densities, detonation velocities and pressures, and impact sensitivities, were obtained from theoretical calculations or experimental measurements. With different task-specific explosophores, the representative energetic compounds 6b and 18 exhibit great potential as high performance insensitive energetic materials and organic primary explosives, respectively. This work gives the classic Dimroth rearrangement new vitality to access diversified task-specific energetic materials.

Graphical abstract: Tunable Dimroth rearrangement of versatile 1,2,3-triazoles towards high-performance energetic materials

Supplementary files

Article information

Article type
Paper
Submitted
05 Jan 2021
Accepted
27 Apr 2021
First published
27 Apr 2021

J. Mater. Chem. A, 2021,9, 12291-12298

Author version available

Tunable Dimroth rearrangement of versatile 1,2,3-triazoles towards high-performance energetic materials

S. Feng, P. Yin, C. He, S. Pang and J. M. Shreeve, J. Mater. Chem. A, 2021, 9, 12291 DOI: 10.1039/D1TA00109D

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