Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

Title: Polycyclic N-oxides: high performing, low sensitivity energetic materials

Journal Article · · ChemComm
DOI: https://doi.org/10.1039/c8cc09653h · OSTI ID:1657122
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2];  [2]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
  2. Naval Research Lab. (NRL), Washington, DC (United States)
+ Show Author Affiliations

For this study, polycyclic N-oxides were developed based on the heterocycles 1,2,4,5-tetrazine and 4H,8H-difurazano[3,4-b:3’,4’-e]pyrazine. The new compounds are energetic and have excellent explosive properties, while maintaining low mechanical sensitivities. Most notably, compound 7 is thermally stable, insensitive, and and has superior detonation properties to the state-of-the-art insensitive high explosive, 1,3,5-triamino-2,4,6-trinitrobenzene.

Research Organization:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Organization:
US Department of the Navy, Office of Naval Research (ONR); USDOE
Grant/Contract Number:
89233218CNA000001
OSTI ID:
1657122
Report Number(s):
LA-UR--18-28923
Journal Information:
ChemComm, Journal Name: ChemComm Journal Issue: 17 Vol. 55; ISSN 1359-7345
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (45)

Tetraazapentalene Chemistry: Unexpected Intramolecular Electron Rearrangement Induced by Highly Reactiveψ-Dinitroso Substituents journal November 2005
Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System journal September 2015
Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO) journal July 2016
An Energetic Triazolo-1,2,4-Triazine and its N-Oxide journal November 2016
Tetraazapentalene Chemistry: Unexpected Intramolecular Electron Rearrangement Induced by Highly Reactiveψ-Dinitroso Substituents journal November 2005
Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System journal September 2015
Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO) journal July 2016
An Energetic Triazolo-1,2,4-Triazine and its N-Oxide journal November 2016
Azido and Tetrazolo 1,2,4,5-Tetrazine N-Oxides journal February 2017
Synthesis, Characterization, and Energetic Properties of 6-Amino-tetrazolo[1,5-b]-1,2,4,5-tetrazine-7- N -oxide: A Nitrogen-Rich Material with High Density journal March 2015
1,2,3-Triazolo[4,5,- e ]furazano[3,4,- b ]pyrazine 6-Oxide-A Fused Heterocycle with a Roving Hydrogen Forms a New Class of Insensitive Energetic Materials journal November 2013
Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines journal October 2017
Dense energetic compounds of carbon, hydrogen, nitrogen, and oxygen atoms. V. 1,2,7,8-bisfuroxano-3,4,9,10-tetranitro-5, 11-dehydro-5H, 11H-benzotriazolo[2, 1-a]benzotriazole (BTBB) journal September 1995
Chemistry of furazano[3,4-b]pyrazine. 1. Synthesis and thermodynamic appraisal of 4,8-dihydrodifurazano[3,4-b,e]pyrazine and its derivatives journal February 1997
Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials journal June 2017
Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N -Heterocyclic Frameworks in High Energy Density Materials journal December 2015
Advances in Tetrazine Bioorthogonal Chemistry Driven by the Synthesis of Novel Tetrazines and Dienophiles journal April 2018
Cocrystal Engineering of a High Nitrogen Energetic Material journal December 2017
Molecular-Scale Electronics: From Concept to Function journal March 2016
Organic Optoelectronic Materials: Mechanisms and Applications journal October 2016
Bis(arylene-ethynylene)- s -tetrazines: A Promising Family of n -Type Organic Semiconductors? journal August 2015
2,3,5,6-Tetra(1 H -tetrazol-5-yl)pyrazine: A Thermally Stable Nitrogen-Rich Energetic Material journal February 2018
Tetrabromoterepthalic Acid in Designing Co-crystals and Salts: Modification of Optical Properties and Schottky Barrier Effect journal December 2013
Experimental X-ray Diffraction Study of Stacking Interaction in Crystals of Two Furazan[3,4- b ]pyrazines journal October 2014
Crystal Packing of Low-Sensitivity and High-Energy Explosives journal August 2014
Crystal Packing of Impact-Sensitive High-Energy Explosives journal October 2014
New Coplanar (ABA) n -Type Donor−Acceptor π-Conjugated Copolymers Constituted of Alkylthiophene (Unit A) and Pyridazine (Unit B):  Synthesis Using Hexamethylditin, Self-Organized Solid Structure, and Optical and Electrochemical Properties of the Copolymers journal November 2005
Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics journal November 2011
s -Tetrazines as Building Blocks for New Functional Molecules and Molecular Materials journal June 2010
Balancing Excellent Performance and High Thermal Stability in a Dinitropyrazole Fused 1,2,3,4-Tetrazine journal September 2017
Monochromophoric Design Strategy for Tetrazine-Based Colorful Bioorthogonal Probes with a Single Fluorescent Core Skeleton journal December 2017
Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations journal January 2006
Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations journal May 2009
The unique synthesis and energetic properties of a novel fused heterocycle: 7-nitro-4-oxo-4,8-dihydro-[1,2,4]triazolo[5,1-d][1,2,3,5]tetrazine 2-oxide and its energetic salts journal January 2015
Synthesis, characterization and properties of heat-resistant explosive materials: polynitroaromatic substituted difurazano[3,4-b:3′,4′-e]pyrazines journal January 2015
A high density pyrazolo-triazine explosive (PTX) journal January 2015
N-functionalized nitroxy/azido fused-ring azoles as high-performance energetic materials journal January 2016
Redox-active ligand controlled selectivity of vanadium oxidation on Au(100) journal January 2018
Photochemical syntheses, transformations, and bioorthogonal chemistry of trans -cycloheptene and sila trans -cycloheptene Ag( i ) complexes journal January 2018
Combined scanning electrochemical and fluorescence microscopies using a tetrazine as a single redox and luminescent (electrofluorochromic) probe journal January 2018
Synthesis of unsubstituted 4H,8H-bisfurazano[3,4-b:3′,4′-e]pyrazine journal January 1996
Synthesis of trisfurazanylamine derivatives journal January 2001
Ultrafast Long-Range Charge Separation in Organic Semiconductor Photovoltaic Diodes journal December 2013
Ultrafast Long-Range Charge Separation in Organic Semiconductor Photovoltaic Diodes conference January 2014
Chemistry of High-Energy Materials book October 2015

Cited By (8)

Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations journal September 2019
Dimethoxycarbonyl Groups Surrounding a Symmetric Diaminobistetrazole Ring: Exploring New Green Energetic Materials journal October 2019
Synthesis and Characterization of 3‐(5‐(Fluorodinitromethyl)‐1 H ‐1,2,4‐triazol‐3‐yl)‐4‐nitrofurazan: A Novel Promising Energetic Component of Boron‐based Fuels for Rocket Ramjet Engines journal October 2019
Computational insight into a new family of functionalized tetrazole- N -oxides as high-energy density materials journal January 2019
3-Nitramino-6-hydroxy-1,2,4,5-tetrazine and its alkaline earth metal salts: an effective strategy to balance energy density and safety of energetic compounds journal May 2020
Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations journal September 2019
3-Nitramino-6-hydroxy-1,2,4,5-tetrazine and its alkaline earth metal salts: an effective strategy to balance energy density and safety of energetic compounds text January 2020
3-Nitramino-6-hydroxy-1,2,4,5-tetrazine and its alkaline earth metal salts: an effective strategy to balance energy density and safety of energetic compounds text January 2020

Linked Research (3)

Similar Records

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY