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Title: Synthesis and Electrochemical Behavior of Electron-Rich s-Tetrazine and Triazolo-tetrazine Nitrate Esters

Abstract

Here, we have prepared energetic nitrate ester derivatives of 1,2,4,5-tetrazine and 1,2,4-triazolo[4,3-b]-[1,2,4,5]-tetrazine ring systems as model compounds to study the electrochemical behavior of tetrazines in the presence of explosive groups. The model compounds showed lower thermal stabilities relative to PETN (pentaerythritol tetranitrate), but slightly improved mechanical sensitivities. The presence of electron-rich amine donors leads to a cathodic shift of the tetrazine redox potentials relative to those of previously reported tetrazine explosives. At these potentials, electron-rich tetrazines with either covalently bound or co-dissolved nitrate ester groups are irreversibly reduced. Effectively, changes in the electronic structure of tetrazines affect their electrochemical response to the presence of nitrate ester groups. Thus, it may be possible to develop tetrazine-based electrochemical sensors for the detection of specific explosives and electrocatalysts for their disposal.

Authors:
 [1]; ORCiD logo [1]; ORCiD logo [1];  [1]; ORCiD logo [1]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Publication Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE Laboratory Directed Research and Development (LDRD) Program; USDOE National Nuclear Security Administration (NNSA)
OSTI Identifier:
1499341
Alternate Identifier(s):
OSTI ID: 1401857
Report Number(s):
LA-UR-16-23402
Journal ID: ISSN 0947-6539
Grant/Contract Number:  
89233218CNA000001
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 22; Journal Issue: 30; Journal ID: ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Myers, Thomas Winfield, Snyder, Christopher J., Chavez, David E., Scharff, Robert Jason, and Veauthier, Jacqueline Marie. Synthesis and Electrochemical Behavior of Electron-Rich s-Tetrazine and Triazolo-tetrazine Nitrate Esters. United States: N. p., 2016. Web. doi:10.1002/chem.201601422.
Myers, Thomas Winfield, Snyder, Christopher J., Chavez, David E., Scharff, Robert Jason, & Veauthier, Jacqueline Marie. Synthesis and Electrochemical Behavior of Electron-Rich s-Tetrazine and Triazolo-tetrazine Nitrate Esters. United States. doi:10.1002/chem.201601422.
Myers, Thomas Winfield, Snyder, Christopher J., Chavez, David E., Scharff, Robert Jason, and Veauthier, Jacqueline Marie. Mon . "Synthesis and Electrochemical Behavior of Electron-Rich s-Tetrazine and Triazolo-tetrazine Nitrate Esters". United States. doi:10.1002/chem.201601422. https://www.osti.gov/servlets/purl/1499341.
@article{osti_1499341,
title = {Synthesis and Electrochemical Behavior of Electron-Rich s-Tetrazine and Triazolo-tetrazine Nitrate Esters},
author = {Myers, Thomas Winfield and Snyder, Christopher J. and Chavez, David E. and Scharff, Robert Jason and Veauthier, Jacqueline Marie},
abstractNote = {Here, we have prepared energetic nitrate ester derivatives of 1,2,4,5-tetrazine and 1,2,4-triazolo[4,3-b]-[1,2,4,5]-tetrazine ring systems as model compounds to study the electrochemical behavior of tetrazines in the presence of explosive groups. The model compounds showed lower thermal stabilities relative to PETN (pentaerythritol tetranitrate), but slightly improved mechanical sensitivities. The presence of electron-rich amine donors leads to a cathodic shift of the tetrazine redox potentials relative to those of previously reported tetrazine explosives. At these potentials, electron-rich tetrazines with either covalently bound or co-dissolved nitrate ester groups are irreversibly reduced. Effectively, changes in the electronic structure of tetrazines affect their electrochemical response to the presence of nitrate ester groups. Thus, it may be possible to develop tetrazine-based electrochemical sensors for the detection of specific explosives and electrocatalysts for their disposal.},
doi = {10.1002/chem.201601422},
journal = {Chemistry - A European Journal},
issn = {0947-6539},
number = 30,
volume = 22,
place = {United States},
year = {2016},
month = {6}
}

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Cited by: 6 works
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Figures / Tables:

Scheme 1 Scheme 1: Attempted reactions of TrisTN with tetrazine electrophiles.

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