N-functionalized nitroxy/azido fused-ring azoles as high-performance energetic materials

Jiaheng Zhang, Ping Yin, Lauren A. Mitchell, Damon A. Parrish, Jean'Ne M. Shreeve

Research output: Contribution to journalArticlepeer-review

54 Scopus citations


A series of fused ring-based nitrate esters/azides and a coupled-ring-based nitrate ester were prepared using a simple and efficient nitrogen-functionalization approach. All new energetic compounds were fully characterized. Structures of four (1-4) were further confirmed by single crystal X-ray diffraction. These nitrate esters have good thermal stabilities and high densities. Energetic performance was evaluated by using EXPLO5 v6.01 based on measured densities and calculated heats of formation (Gaussian 03 (Revision D. 01)). The results show that some of the representative fused ring-based nitrate esters exhibit good detonation properties, for example, 1 (vD, 8674 m s-1; P, 33.1 Gpa) and 2 (vD, 8669 m s-1; P, 33.4 Gpa), that approach those of current high explosive benchmarks, such as 1,3,5-trinitroperhydro-1,3,5-triazine (RDX). Sensitivity data based on impact and friction tests show these compounds have better stabilities than the traditional nitrate ester explosive, pentaerythritol tetranitrate (PETN).

Original languageEnglish (US)
Pages (from-to)7430-7436
Number of pages7
JournalJournal of Materials Chemistry A
Issue number19
StatePublished - 2016

Bibliographical note

Funding Information:
We are grateful to Dr Clifford Bedford -ONR (NOOO14-12-1- 0536) and the Defense Threat Reduction Agency (HDTRA 1-11-1- 0034).

Publisher Copyright:
© 2016 The Royal Society of Chemistry.


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