Comprehensive End-to-End Design of Novel High Energy Density Materials: I. Synthesis and Characterization of Oxadiazole Based Heterocycles

Tsyshevsky, Roman; Pagoria, Philip; Zhang, Maoxi; Racoveanu, Ana; Parrish, Damon A.; Smirnov, Aleksandr S.; Kuklja, Maija M.

doi:10.1021/acs.jpcc.7b07584

Title: 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:

Tsyshevsky, Roman ^[1]; Pagoria, Philip ^[2]; Zhang, Maoxi ^[2]; Racoveanu, Ana ^[2]; Parrish, Damon A. ^[3]; Smirnov, Aleksandr S. ^[4];

^[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:: 2017-10-02

Research Org.:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Org.:: USDOE; National Science Foundation (NSF)

OSTI Identifier:: 1483296

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.

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                    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

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                    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.

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@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         = {2017},

  month        = {10}

}

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Journal Article:

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https://doi.org/10.1021/acs.jpcc.7b07584

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Cited by: 16 works

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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 »

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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
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Comprehensive End-to-End Design of Novel High Energy Density Materials: II. Computational Modeling and Predictions
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Tsyshevsky, Roman; Pagoria, Philip; Smirnov, Aleksandr S.
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Molecular Theory of Detonation Initiation: Insight from First Principles Modeling of the Decomposition Mechanisms of Organic Nitro Energetic Materials
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Works referencing / citing this record:

An unexpected method to synthesise 1,2,4-oxadiazolone derivatives: a class of insensitive energetic materials
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Wang, Bohan; Xiong, Hualin; Cheng, Guangbin
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Energetic N -azidomethyl derivatives of polynitro hexaazaisowurtzitanes series: CL-20 analogues having the highest enthalpy
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Luk′yanov, Oleg A.; Parakhin, Vladimir V.; Shlykova, Nina I.
New Journal of Chemistry
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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
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Boosting energetic performance by trimerizing furoxan
journal, January 2018

He, Chunlin; Gao, Haixiang; Imler, Gregory H.
Journal of Materials Chemistry A, Vol. 6, Issue 20
DOI: 10.1039/c8ta02274g

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Title: Comprehensive End-to-End Design of Novel High Energy Density Materials: I. Synthesis and Characterization of Oxadiazole Based Heterocycles

Abstract

Citation Formats

Figures / Tables:

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

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journal, December 2011

Recent approaches to the synthesis of high explosive and energetic materials: A review
journal, March 1984

Derivatives of 5-nitro-1,2,3-2H-triazole – high performance energetic materials
journal, January 2013

5,5′‐Bis(2,4,6‐trinitrophenyl)‐2,2′‐bi(1,3,4‐oxadiazole) (TKX‐55): Thermally Stable Explosive with Outstanding Properties
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Some Reactions of 3,6-Bis(4-amino-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazine
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4-[4-(4-Amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl]-1,2,5-oxadiazol-3-amine
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An Effective Method for the Oxidation of Aminofurazans to Nitrofurazans
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