3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies

Ping Yin; Jiaheng Zhang; Lauren A. Mitchell; Damon A. Parrish; Jean'ne M. Shreeve

doi:10.1002/anie.201606894

3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies

Ping Yin, Jiaheng Zhang, Lauren A. Mitchell, Damon A. Parrish, Jean'ne M. Shreeve^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

108 Citations (Scopus)

Abstract

A family of 3,6-dinitropyrazolo[4,3-c]pyrazole-based energetic compounds was synthesized by using versatile N-functionalization strategies. Subsequently, nine ionic derivatives of the N,N′-(3,6-dinitropyrazolo[4,3-c]pyrazole-1,4-diyl)dinitramidate anion were prepared by acid-base reactions and fully characterized by infrared, multinuclear NMR spectra, and elemental analysis. The structures of four of these compounds were further confirmed by single-crystal X-ray diffraction. Based on their different physical and detonation properties, these compounds exhibit promising potential as modern energetic materials and can be variously classified as green primary explosives, high-performance secondary explosives, fuel-rich propellants, and propellant oxidizers.

Original language	English
Pages (from-to)	12895-12897
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	41
DOIs	https://doi.org/10.1002/anie.201606894
Publication status	Published - 4 Oct 2016
Externally published	Yes

Keywords

N-functionalization
detonation
energetic materials
fused heterocycle
nitramines

Access to Document

10.1002/anie.201606894

Cite this

Yin, P., Zhang, J., Mitchell, L. A., Parrish, D. A., & Shreeve, J. M. (2016). 3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies. Angewandte Chemie - International Edition, 55(41), 12895-12897. https://doi.org/10.1002/anie.201606894

@article{62ecdc8ab46348bbb1a20b8f56e3c5ff,

title = "3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies",

abstract = "A family of 3,6-dinitropyrazolo[4,3-c]pyrazole-based energetic compounds was synthesized by using versatile N-functionalization strategies. Subsequently, nine ionic derivatives of the N,N′-(3,6-dinitropyrazolo[4,3-c]pyrazole-1,4-diyl)dinitramidate anion were prepared by acid-base reactions and fully characterized by infrared, multinuclear NMR spectra, and elemental analysis. The structures of four of these compounds were further confirmed by single-crystal X-ray diffraction. Based on their different physical and detonation properties, these compounds exhibit promising potential as modern energetic materials and can be variously classified as green primary explosives, high-performance secondary explosives, fuel-rich propellants, and propellant oxidizers.",

keywords = "N-functionalization, detonation, energetic materials, fused heterocycle, nitramines",

author = "Ping Yin and Jiaheng Zhang and Mitchell, {Lauren A.} and Parrish, {Damon A.} and Shreeve, {Jean'ne M.}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = oct,

day = "4",

doi = "10.1002/anie.201606894",

language = "English",

volume = "55",

pages = "12895--12897",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "41",

}

TY - JOUR

T1 - 3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies

AU - Yin, Ping

AU - Zhang, Jiaheng

AU - Mitchell, Lauren A.

AU - Parrish, Damon A.

AU - Shreeve, Jean'ne M.

PY - 2016/10/4

Y1 - 2016/10/4

N2 - A family of 3,6-dinitropyrazolo[4,3-c]pyrazole-based energetic compounds was synthesized by using versatile N-functionalization strategies. Subsequently, nine ionic derivatives of the N,N′-(3,6-dinitropyrazolo[4,3-c]pyrazole-1,4-diyl)dinitramidate anion were prepared by acid-base reactions and fully characterized by infrared, multinuclear NMR spectra, and elemental analysis. The structures of four of these compounds were further confirmed by single-crystal X-ray diffraction. Based on their different physical and detonation properties, these compounds exhibit promising potential as modern energetic materials and can be variously classified as green primary explosives, high-performance secondary explosives, fuel-rich propellants, and propellant oxidizers.

AB - A family of 3,6-dinitropyrazolo[4,3-c]pyrazole-based energetic compounds was synthesized by using versatile N-functionalization strategies. Subsequently, nine ionic derivatives of the N,N′-(3,6-dinitropyrazolo[4,3-c]pyrazole-1,4-diyl)dinitramidate anion were prepared by acid-base reactions and fully characterized by infrared, multinuclear NMR spectra, and elemental analysis. The structures of four of these compounds were further confirmed by single-crystal X-ray diffraction. Based on their different physical and detonation properties, these compounds exhibit promising potential as modern energetic materials and can be variously classified as green primary explosives, high-performance secondary explosives, fuel-rich propellants, and propellant oxidizers.

KW - N-functionalization

KW - detonation

KW - energetic materials

KW - fused heterocycle

KW - nitramines

UR - http://www.scopus.com/inward/record.url?scp=84988836241&partnerID=8YFLogxK

U2 - 10.1002/anie.201606894

DO - 10.1002/anie.201606894

M3 - Article

AN - SCOPUS:84988836241

SN - 1433-7851

VL - 55

SP - 12895

EP - 12897

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 41

ER -

3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this