Comprehensive End-to-End Design of Novel High Energy Density Materials: I. Synthesis and Characterization of Oxadiazole Based Heterocycles
Abstract
A methodology to design novel energetic materials by means of a holistic approach that links synthesis, experimental characterization, quantum-chemical modeling, and statistical empirical evaluation is proposed. An analysis of the revealed structure–property–function correlations in the LLM compound series (oxadiazole-based heterocyclic energetics), BNFF, BNFF-1, LLM-172, LLM-191, and LLM-192, led us to predict, obtain, and characterize a new member in the materials family, LLM-200, which exhibits attractive energetic characteristics compared to known conventional high energy density materials. Finally, while the applied strategy convincingly demonstrated feasibility of the end-to-end design of high energy density materials, there are certain limitations in parallel improvements of sensitivity and performance within a single compound.
- Authors:
-
[1]
- Univ. of Maryland, College Park, MD (United States). Materials Science and Engineering Dept.
- Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States). Energetic Materials Center
- Naval Research Lab. (NRL), Washington, DC (United States)
- Bakhirev Scientific Research Inst. of Mechanical Engineering, Dzerzhinsk, Nizhny Novgorod (Russia)
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
- Sponsoring Org.:
- USDOE; National Science Foundation (NSF)
- OSTI Identifier:
- 1483296
- Alternate Identifier(s):
- OSTI ID: 1874109
- Report Number(s):
- LLNL-JRNL-784804
Journal ID: ISSN 1932-7447
- Grant/Contract Number:
- AC52-07NA27344; AC02-05CH11231
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Physical Chemistry. C
- Additional Journal Information:
- Journal Volume: 121; Journal Issue: 43; Journal ID: ISSN 1932-7447
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Tsyshevsky, Roman, Pagoria, Philip, Zhang, Maoxi, Racoveanu, Ana, Parrish, Damon A., Smirnov, Aleksandr S., and Kuklja, Maija M. Comprehensive End-to-End Design of Novel High Energy Density Materials: I. Synthesis and Characterization of Oxadiazole Based Heterocycles. United States: N. p., 2017.
Web. doi:10.1021/acs.jpcc.7b07584.
Tsyshevsky, Roman, Pagoria, Philip, Zhang, Maoxi, Racoveanu, Ana, Parrish, Damon A., Smirnov, Aleksandr S., & Kuklja, Maija M. Comprehensive End-to-End Design of Novel High Energy Density Materials: I. Synthesis and Characterization of Oxadiazole Based Heterocycles. United States. https://doi.org/10.1021/acs.jpcc.7b07584
Tsyshevsky, Roman, Pagoria, Philip, Zhang, Maoxi, Racoveanu, Ana, Parrish, Damon A., Smirnov, Aleksandr S., and Kuklja, Maija M. Mon .
"Comprehensive End-to-End Design of Novel High Energy Density Materials: I. Synthesis and Characterization of Oxadiazole Based Heterocycles". United States. https://doi.org/10.1021/acs.jpcc.7b07584. https://www.osti.gov/servlets/purl/1483296.
@article{osti_1483296,
title = {Comprehensive End-to-End Design of Novel High Energy Density Materials: I. Synthesis and Characterization of Oxadiazole Based Heterocycles},
author = {Tsyshevsky, Roman and Pagoria, Philip and Zhang, Maoxi and Racoveanu, Ana and Parrish, Damon A. and Smirnov, Aleksandr S. and Kuklja, Maija M.},
abstractNote = {A methodology to design novel energetic materials by means of a holistic approach that links synthesis, experimental characterization, quantum-chemical modeling, and statistical empirical evaluation is proposed. An analysis of the revealed structure–property–function correlations in the LLM compound series (oxadiazole-based heterocyclic energetics), BNFF, BNFF-1, LLM-172, LLM-191, and LLM-192, led us to predict, obtain, and characterize a new member in the materials family, LLM-200, which exhibits attractive energetic characteristics compared to known conventional high energy density materials. Finally, while the applied strategy convincingly demonstrated feasibility of the end-to-end design of high energy density materials, there are certain limitations in parallel improvements of sensitivity and performance within a single compound.},
doi = {10.1021/acs.jpcc.7b07584},
journal = {Journal of Physical Chemistry. C},
number = 43,
volume = 121,
place = {United States},
year = {Mon Oct 02 00:00:00 EDT 2017},
month = {Mon Oct 02 00:00:00 EDT 2017}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 30 works
Citation information provided by
Web of Science
Web of Science
Figures / Tables:
Figure 1: Sketch representation of 3,4-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-2- oxide (BNFF), 3,4-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole (BNFF-1) and 3-(4- amino-1,2,5-oxadiazol-3-yl)-4-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole (ANFF-1), 3,5- Bis-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazole (LLM-191), 3-(4-amino-1,2,5-oxadiazol-3- yl)-5-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazole (LLM-192), and 3,3’-Bis(3-nitro-1,2,5- oxadiazol-4-yl)-5,5’-bi-1,2,4-oxadiazole (LLM-200) shows molecular building blocks in each compound. The color-coded circles are introduced to indicate a particular oxadiazole fragment: the red circle indicates the 1,2,5-oxadiazole-2-oxide ring; themore »
All figures and tables
(9 total)
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Synthesis and Promising Properties of a New Family of High-Density Energetic Salts of 5-Nitro-3-trinitromethyl-1 H -1,2,4-triazole and 5,5′-Bis(trinitromethyl)-3,3′-azo-1 H -1,2,4-triazole
journal, December 2011
- Thottempudi, Venugopal; Shreeve, Jean’ne M.
- Journal of the American Chemical Society, Vol. 133, Issue 49
A review of energetic materials synthesis
journal, February 2002
- Pagoria, Philip F.; Lee, Gregory S.; Mitchell, Alexander R.
- Thermochimica Acta, Vol. 384, Issue 1-2
Recent Advances in the Synthesis of High Explosive Materials
journal, December 2015
- Sabatini, Jesse; Oyler, Karl
- Crystals, Vol. 6, Issue 1
Recent approaches to the synthesis of high explosive and energetic materials: A review
journal, March 1984
- Spear, Robert J.; Wilson, William S.
- Journal of Energetic Materials, Vol. 2, Issue 1-2
Design and Synthesis of Energetic Materials
journal, August 2001
- Fried, Laurence E.; Manaa, M. Riad; Pagoria, Philip F.
- Annual Review of Materials Research, Vol. 31, Issue 1
Derivatives of 5-nitro-1,2,3-2H-triazole – high performance energetic materials
journal, January 2013
- Zhang, Yanqiang; Parrish, Damon A.; Shreeve, Jean'ne M.
- J. Mater. Chem. A, Vol. 1, Issue 3
Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate
journal, January 2012
- Fischer, Niko; Fischer, Dennis; Klapötke, Thomas M.
- Journal of Materials Chemistry, Vol. 22, Issue 38
Energetic Salts with π-Stacking and Hydrogen-Bonding Interactions Lead the Way to Future Energetic Materials
journal, January 2015
- Zhang, Jiaheng; Zhang, Qinghua; Vo, Thao T.
- Journal of the American Chemical Society, Vol. 137, Issue 4
Azole-Based Energetic Salts
journal, November 2011
- Gao, Haixiang; Shreeve, Jean’ne M.
- Chemical Reviews, Vol. 111, Issue 11
Searching for Low-Sensitivity Cast-Melt High-Energy-Density Materials: Synthesis, Characterization, and Decomposition Kinetics of 3,4-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-2-oxide
journal, February 2015
- Tsyshevsky, Roman; Pagoria, Philip; Zhang, Maoxi
- The Journal of Physical Chemistry C, Vol. 119, Issue 7
5,5′‐Bis(2,4,6‐trinitrophenyl)‐2,2′‐bi(1,3,4‐oxadiazole) (TKX‐55): Thermally Stable Explosive with Outstanding Properties
journal, March 2016
- Klapötke, Thomas M.; Witkowski, Tomasz G.
- ChemPlusChem, Vol. 81, Issue 4
Synthesis and Characterization of Bisnitrofurazanofuroxan
journal, May 2010
- Lim, Choong-Hwan; Kim, Tae-Keun; Kim, Kyung-Ho
- Bulletin of the Korean Chemical Society, Vol. 31, Issue 5
An Investigation on Thermal Decomposition of DNTF-CMDB Propellants
journal, December 2007
- Zheng, Wei; Wang, Jiangning; Ren, Xiaoning
- Propellants, Explosives, Pyrotechnics, Vol. 32, Issue 6
Thermal and Combustion Properties of 3,4-Bis(3-nitrofurazan-4-yl)furoxan (DNTF)
journal, June 2012
- Sinditskii, Valery P.; Burzhava, Anna V.; Sheremetev, Aleksey B.
- Propellants, Explosives, Pyrotechnics, Vol. 37, Issue 5
Synthesis and Characterization of BNFF Analogues
journal, August 2012
- Kim, Tae-Keun; Choe, Jun-Ho; Lee, Byung-Woo
- Bulletin of the Korean Chemical Society, Vol. 33, Issue 8
A new synthesis of adenine and 4-aminoimidazole-5-carboxamide
journal, September 1965
- Ichikawa, Takehiko; Kato, Tetsuya; Takenishi, Tadao
- Journal of Heterocyclic Chemistry, Vol. 2, Issue 3
3-(4-Amino-1,2,5-oxadiazol-3-yl)-4-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole
journal, May 2014
- Pagoria, Philip; Zhang, Maoxi; Racoveanu, Ana
- Molbank, Vol. 2014, Issue 2
Some Reactions of 3,6-Bis(4-amino-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazine
journal, June 2004
- Shaposhnikov, S. D.; Romanova, T. V.; Spiridonova, N. P.
- Russian Journal of Organic Chemistry, Vol. 40, Issue 6
4-[4-(4-Amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl]-1,2,5-oxadiazol-3-amine
journal, April 2012
- Jia, Si-Yuan; Wang, Bo-Zhou; Fan, Xue-Zhong
- Acta Crystallographica Section E Structure Reports Online, Vol. 68, Issue 5
An Effective Method for the Oxidation of Aminofurazans to Nitrofurazans
journal, January 1994
- Novikova, Tat’yana S.; Mel’nikova, Tat’yana M.; Kharitonova, Olga V.
- Mendeleev Communications, Vol. 4, Issue 4
Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine
journal, August 2016
- Astrat’ev, A. A.; Stepanov, A. I.; Sannikov, V. S.
- Russian Journal of Organic Chemistry, Vol. 52, Issue 8
Synthesis and properties of 4-amino-3-cyanofurazan
journal, May 1994
- Andrianov, V. G.; Eremeev, A. V.
- Chemistry of Heterocyclic Compounds, Vol. 30, Issue 5, p. 608-611
Combination of 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Moieties for the Generation of High-Performance Energetic Materials
journal, June 2015
- Wei, Hao; He, Chunlin; Zhang, Jiaheng
- Angewandte Chemie, Vol. 127, Issue 32
New synthesis of 1,2,4-oxadiazoles
journal, January 1990
- Yarovenko, V. N.; Taralashvili, V. K.; Zavarzin, I. V.
- Tetrahedron, Vol. 46, Issue 11, p. 3941-3952
A convenient synthesis of 3-substituted 5-guanidino-1,2,4-oxadiazoles
journal, January 1994
- Yarovenko, V. N.; Shirinyan, V. Z.; Zavarzin, I. V.
- Russian Chemical Bulletin, Vol. 43, Issue 1
3,3′-Bi(1,2,4-oxadiazoles) Featuring the Fluorodinitromethyl and Trinitromethyl Groups
journal, May 2014
- Kettner, Marcos A.; Karaghiosoff, Konstantin; Klapötke, Thomas M.
- Chemistry - A European Journal, Vol. 20, Issue 25
A Method for Obtaining and Analyzing Sensitivity Data
journal, March 1948
- Dixon, W. J.; Mood, A. M.
- Journal of the American Statistical Association, Vol. 43, Issue 241
Gaussian-3 theory using density functional geometries and zero-point energies
journal, April 1999
- Baboul, Anwar G.; Curtiss, Larry A.; Redfern, Paul C.
- The Journal of Chemical Physics, Vol. 110, Issue 16
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007
- Zhao, Yan; Truhlar, Donald G.
- Theoretical Chemistry Accounts, Vol. 120, Issue 1-3
Computational Design of Novel Energetic Materials: Dinitro-bis-triazolo-tetrazine
journal, April 2015
- Tsyshevsky, Roman V.; Pagoria, Philip; Kuklja, Maija M.
- The Journal of Physical Chemistry C, Vol. 119, Issue 16
Accurate reaction paths using a Hessian based predictor–corrector integrator
journal, June 2004
- Hratchian, Hrant P.; Schlegel, H. Bernhard
- The Journal of Chemical Physics, Vol. 120, Issue 21
Using Hessian Updating To Increase the Efficiency of a Hessian Based Predictor-Corrector Reaction Path Following Method
journal, October 2004
- Hratchian, H. P.; Schlegel, H. B.
- Journal of Chemical Theory and Computation, Vol. 1, Issue 1
Reaction-rate theory: fifty years after Kramers
journal, April 1990
- Hänggi, Peter; Talkner, Peter; Borkovec, Michal
- Reviews of Modern Physics, Vol. 62, Issue 2
Generalized transition state theory. Classical mechanical theory and applications to collinear reactions of hydrogen molecules
journal, April 1979
- Garrett, Bruce C.; Truhlar, Donald G.
- The Journal of Physical Chemistry, Vol. 83, Issue 8
Ab Initio Kinetics of Gas Phase Decomposition Reactions
journal, December 2010
- Sharia, Onise; Kuklja, Maija M.
- The Journal of Physical Chemistry A, Vol. 114, Issue 48
Modeling Thermal Decomposition Mechanisms in Gaseous and Crystalline Molecular Materials: Application to β-HMX
journal, November 2011
- Sharia, Onise; Kuklja, Maija M.
- The Journal of Physical Chemistry B, Vol. 115, Issue 44
Surface-Enhanced Decomposition Kinetics of Molecular Materials Illustrated with Cyclotetramethylene-tetranitramine
journal, May 2012
- Sharia, Onise; Kuklja, Maija M.
- The Journal of Physical Chemistry C, Vol. 116, Issue 20
Comprehensive assessment of physicochemical properties of new energetic materials
journal, October 2016
- Smirnov, A. S.; Smirnov, S. P.; Pivina, T. S.
- Russian Chemical Bulletin, Vol. 65, Issue 10
Important aspects of behaviour of organic energetic compounds: a review
journal, June 2001
- Sikder, A. K.; Maddala, G.; Agrawal, J. P.
- Journal of Hazardous Materials, Vol. 84, Issue 1
Thermochemische untersuchungen an nitraminen
journal, July 1973
- Krien, G.; Licht, H. H.; Zierath, J.
- Thermochimica Acta, Vol. 6, Issue 5
Thermochemistry of N-nitro- and N -nitrosoamines of the alicyclic series
journal, August 1974
- Pepekin, V. I.; Matyushin, Yu. N.; Lebedev, Yu. A.
- Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 23, Issue 8
Comprehensive End-to-End Design of Novel High Energy Density Materials: II. Computational Modeling and Predictions
journal, October 2017
- Tsyshevsky, Roman; Pagoria, Philip; Smirnov, Aleksandr S.
- The Journal of Physical Chemistry C, Vol. 121, Issue 43
Thermal Decomposition of Energetic Materials. 66. Kinetic Compensation Effects in HMX, RDX, and NTO
journal, November 1994
- Brill, T. B.; Gongwer, P. E.; Williams, G. K.
- The Journal of Physical Chemistry, Vol. 98, Issue 47
Thermochemical properties and non-isothermal decomposition reaction kinetics of 3,4-dinitrofurazanfuroxan (DNTF)
journal, September 2004
- Feng-qi, Zhao; Pei, Chen; Rong-zu, Hu
- Journal of Hazardous Materials, Vol. 113, Issue 1-3
Molecular Theory of Detonation Initiation: Insight from First Principles Modeling of the Decomposition Mechanisms of Organic Nitro Energetic Materials
journal, February 2016
- Tsyshevsky, Roman; Sharia, Onise; Kuklja, Maija
- Molecules, Vol. 21, Issue 2
Works referencing / citing this record:
An unexpected method to synthesise 1,2,4-oxadiazolone derivatives: a class of insensitive energetic materials
journal, January 2018
- Wang, Bohan; Xiong, Hualin; Cheng, Guangbin
- New Journal of Chemistry, Vol. 42, Issue 24
Energetic N -azidomethyl derivatives of polynitro hexaazaisowurtzitanes series: CL-20 analogues having the highest enthalpy
journal, January 2020
- Luk′yanov, Oleg A.; Parakhin, Vladimir V.; Shlykova, Nina I.
- New Journal of Chemistry
1,2,4‐Oxadiazole‐Bridged Polynitropyrazole Energetic Materials with Enhanced Thermal Stability and Low Sensitivity
journal, October 2019
- Yan, Tingou; Cheng, Guangbin; Yang, Hongwei
- ChemPlusChem, Vol. 84, Issue 10
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.