Issue 14, 2022

Engineering bistetrazoles: (E)-5,5′-(ethene-1,2-diyl)bis(1H-tetrazol-1-ol) as a new planar high-energy-density material

Abstract

Energetic properties of bistetrazole derivatives are improved by the step-by-step introduction of functionalities which improve heat of formation, density, and oxygen content. The incorporation of unsaturation between bis(1H-tetrazol-5-yl) and bis(1H-tetrazol-1-ol) derivatives leads to planarity which enhances the density of the final product. In this manuscript, we have synthesized compounds 1,2-di(1H-tetrazol-5-yl)ethane (4), (E)-1,2-di(1H-tetrazol-5-yl)ethene (5), and (E)-5,5′-(ethene-1,2-diyl)bis(1H-tetrazol-1-ol), (6) using readily available starting materials. Their corresponding dihydroxylammonium salts 7, 8 and 9 are obtained by reacting two equivalents of hydroxylamine (50% in water). New compounds are analyzed using IR, EA, DSC and multinuclear NMR spectroscopy (1H, 13C and 15N). The solid-state structures of compounds 6, 7, 8 and 9 are confirmed by single-crystal X-ray diffraction. The energetic performances are calculated using the EXPLO5 (v6.06.02) code and the sensitivities towards external stimuli such as friction and impact are determined according to BAM standard. Compound 6 {(E)-5,5′-(ethene-1,2-diyl)bis(1H-tetrazol-1-ol)} exhibits a surprisingly high density of 1.91 g cm−3 at 100 K (1.86 g cm−3 at 298 K). Its detonation velocity (9017 m s−1) is considerably superior to those of RDX (8795 m s−1), which suggests it is a competitive high-energy-density material.

Graphical abstract: Engineering bistetrazoles: (E)-5,5′-(ethene-1,2-diyl)bis(1H-tetrazol-1-ol) as a new planar high-energy-density material

Supplementary files

Article information

Article type
Paper
Submitted
10 Jun 2022
Accepted
23 Jun 2022
First published
23 Jun 2022
This article is Open Access
Creative Commons BY license

Mater. Adv., 2022,3, 6062-6068

Engineering bistetrazoles: (E)-5,5′-(ethene-1,2-diyl)bis(1H-tetrazol-1-ol) as a new planar high-energy-density material

J. Singh, R. J. Staples and J. M. Shreeve, Mater. Adv., 2022, 3, 6062 DOI: 10.1039/D2MA00664B

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