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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

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];  [2];  [2];  [2];  [3];  [4]; ORCiD logo [1]
  1. Univ. of Maryland, College Park, MD (United States). Materials Science and Engineering Dept.
  2. Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States). Energetic Materials Center
  3. Naval Research Lab. (NRL), Washington, DC (United States)
  4. 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.:
National Science Foundation (NSF); USDOE National Nuclear Security Administration (NNSA)
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; Chemistry - Chemical explosives

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 = {2017},
month = {10}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 16 works
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Figures / Tables:

Figure 1 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 » blue circle shows the 1,2,5- oxadiazole ring; and the green circle stands for the 1,2,4-oxadiazole ring.« less

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