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Synlett 2024; 35(17): 1997-2002
DOI: 10.1055/s-0043-1775365
letter
Energetic Molecules

A π-Stacked Highly Stable, Insensitive, Energy-Containing Material with a Useful Planar Structure

Shuliang Liu
a   School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China
,
Yuan Qi
a   School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China
,
Peng-cheng Zhang∗
b   Research Institute of Chemical Defense, Academy of Military Sciences, Beijing 102205, P. R. of China
,
Qiuhan Lin∗
a   School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China
› Author AffiliationsWe are grateful to the National Natural Science Foundation of China (22375095) for funding this work.
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Abstract

π-Stacking is common in materials, but different π–π stacking modes remarkably affect the properties and performances of materials. In particular, weak interactions, π-stacking and hydrogen bonding often have a significant impact on the stability and sensitivity of high-energetic compounds. A fused [5,7,5]-tricyclic energetic compound with a conjugated structure has been designed and synthesized. 4H-[1,2,5]Oxadiazolo[3,4-e][1,2,4]triazolo[3,4-g][1,2,4]triazepin-8-amine is obtained in 48% yield from 3-amino-4-carboxy-1,2,5-oxadiazole through an efficient two-step reaction. Owing to its layered planar structure and weak π interactions between layers, 4H-[1,2,5]oxadiazolo[3,4-e][1,2,4]triazolo[3,4-g][1,2,4]triazepin-8-amine exhibits high thermal stability (T d = 318 °C), low sensitivity (IS = 40 J, FS = 360 N), and relatively excellent detonation performance (D = 7059 ms–1, P = 20.2 GPa). This detonation performance is superior to that of the conventional explosive TNT. The developed procedure provides a new method for the synthesis of fused ring compounds.

Key words

energetic materials - explosives - nitrogen heterocycles - π-stacking - detonation - planar structure

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775365.
  • Supporting Information


Publication History

Received: 12 December 2023

Accepted after revision: 14 May 2024

Article published online:
02 July 2024

© 2024. Thieme. All rights reserved

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