Fluorinated Aryl Sulfonimide Tagged (FAST) salts: modular synthesis and structure–property relationships for battery applications
Abstract
Solid-state electrolytes are attracting great interest for their applications in potentially safe and stable high-capacity energy storage technologies. Lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) is widely used as a lithium ion source, especially in solid-state polymer electrolytes, due to its solubility and excellent chemical and electrochemical stability. Unfortunately, chemically inert LiTFSI cannot be easily modified to optimize its properties or allow for conjugation to other molecules, polymers, or substrates to prepare single-ion conducting polymer electrolytes. Chemical modifications of TFSI often erode its advantageous properties. Herein, we introduce Fluorinated Aryl Sulfonimide Tagged (FAST) salts, which are derived from successive nucleophilic aromatic substitution (SNAr) reactions. Experimental studies and density functional theory calculations were used to assess the electrochemical oxidative stabilities, chemical stabilities, and degrees of ion dissociation of FAST salts as a function of their structures. FAST salts offer a platform for accessing functional sulfonimides without sacrificing many of the advantageous properties of TFSI.
- Authors:
-
[1];
[2];
[1];
[3];
[1];
[4];
[3];
[1]
- Department of Chemistry, Massachusetts Institute of Technology, Cambridge, USA
- Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, USA
- Department of Mechanical Engineering, Massachusetts Institute of Technology, Cambridge, USA
- Samsung Advanced Institute of Technology (SAIT), Burlington, USA
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1483900
- Alternate Identifier(s):
- OSTI ID: 1434114; OSTI ID: 1543790
- Grant/Contract Number:
- AC02-5CH11231; AC02-05CH11231
- Resource Type:
- Published Article
- Journal Name:
- Energy & Environmental Science
- Additional Journal Information:
- Journal Name: Energy & Environmental Science Journal Volume: 11 Journal Issue: 5; Journal ID: ISSN 1754-5692
- Publisher:
- Royal Society of Chemistry (RSC)
- Country of Publication:
- United Kingdom
- Language:
- English
- Subject:
- 25 ENERGY STORAGE; Chemistry; Energy & Fuels; Engineering; Environmental Sciences & Ecology
Citation Formats
Huang, Mingjun, Feng, Shuting, Zhang, Wenxu, Giordano, Livia, Chen, Mao, Amanchukwu, Chibueze V., Anandakathir, Robinson, Shao-Horn, Yang, and Johnson, Jeremiah A. Fluorinated Aryl Sulfonimide Tagged (FAST) salts: modular synthesis and structure–property relationships for battery applications. United Kingdom: N. p., 2018.
Web. doi:10.1039/C7EE03509H.
Huang, Mingjun, Feng, Shuting, Zhang, Wenxu, Giordano, Livia, Chen, Mao, Amanchukwu, Chibueze V., Anandakathir, Robinson, Shao-Horn, Yang, & Johnson, Jeremiah A. Fluorinated Aryl Sulfonimide Tagged (FAST) salts: modular synthesis and structure–property relationships for battery applications. United Kingdom. https://doi.org/10.1039/C7EE03509H
Huang, Mingjun, Feng, Shuting, Zhang, Wenxu, Giordano, Livia, Chen, Mao, Amanchukwu, Chibueze V., Anandakathir, Robinson, Shao-Horn, Yang, and Johnson, Jeremiah A. Wed .
"Fluorinated Aryl Sulfonimide Tagged (FAST) salts: modular synthesis and structure–property relationships for battery applications". United Kingdom. https://doi.org/10.1039/C7EE03509H.
@article{osti_1483900,
title = {Fluorinated Aryl Sulfonimide Tagged (FAST) salts: modular synthesis and structure–property relationships for battery applications},
author = {Huang, Mingjun and Feng, Shuting and Zhang, Wenxu and Giordano, Livia and Chen, Mao and Amanchukwu, Chibueze V. and Anandakathir, Robinson and Shao-Horn, Yang and Johnson, Jeremiah A.},
abstractNote = {Solid-state electrolytes are attracting great interest for their applications in potentially safe and stable high-capacity energy storage technologies. Lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) is widely used as a lithium ion source, especially in solid-state polymer electrolytes, due to its solubility and excellent chemical and electrochemical stability. Unfortunately, chemically inert LiTFSI cannot be easily modified to optimize its properties or allow for conjugation to other molecules, polymers, or substrates to prepare single-ion conducting polymer electrolytes. Chemical modifications of TFSI often erode its advantageous properties. Herein, we introduce Fluorinated Aryl Sulfonimide Tagged (FAST) salts, which are derived from successive nucleophilic aromatic substitution (SNAr) reactions. Experimental studies and density functional theory calculations were used to assess the electrochemical oxidative stabilities, chemical stabilities, and degrees of ion dissociation of FAST salts as a function of their structures. FAST salts offer a platform for accessing functional sulfonimides without sacrificing many of the advantageous properties of TFSI.},
doi = {10.1039/C7EE03509H},
journal = {Energy & Environmental Science},
number = 5,
volume = 11,
place = {United Kingdom},
year = {Wed May 16 00:00:00 EDT 2018},
month = {Wed May 16 00:00:00 EDT 2018}
}
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Reactions in the Rechargeable Lithium–O 2 Battery with Alkyl Carbonate Electrolytes
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Instability of Poly(ethylene oxide) upon Oxidation in Lithium–Air Batteries
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Issues and challenges facing rechargeable lithium batteries
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Lithium battery chemistries enabled by solid-state electrolytes
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Opportunities and challenges for a sustainable energy future
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Towards greener and more sustainable batteries for electrical energy storage
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Advances in understanding mechanisms underpinning lithium–air batteries
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- Nature Energy, Vol. 1, Issue 9
Advances in lithium–sulfur batteries based on multifunctional cathodes and electrolytes
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- Pang, Quan; Liang, Xiao; Kwok, Chun Yuen
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The future cost of electrical energy storage based on experience rates
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- Schmidt, O.; Hawkes, A.; Gambhir, A.
- Nature Energy, Vol. 2, Issue 8
Single-ion BAB triblock copolymers as highly efficient electrolytes for lithium-metal batteries
journal, March 2013
- Bouchet, Renaud; Maria, Sébastien; Meziane, Rachid
- Nature Materials, Vol. 12, Issue 5
Electrolytes for solid-state lithium rechargeable batteries: recent advances and perspectives
journal, January 2011
- Quartarone, Eliana; Mustarelli, Piercarlo
- Chemical Society Reviews, Vol. 40, Issue 5
Lithium–oxygen batteries: bridging mechanistic understanding and battery performance
journal, January 2013
- Lu, Yi-Chun; Gallant, Betar M.; Kwabi, David G.
- Energy & Environmental Science, Vol. 6, Issue 3
Natural population analysis
journal, July 1985
- Reed, Alan E.; Weinstock, Robert B.; Weinhold, Frank
- The Journal of Chemical Physics, Vol. 83, Issue 2
Enhancing electrochemical intermediate solvation through electrolyte anion selection to increase nonaqueous Li–O 2 battery capacity
journal, July 2015
- Burke, Colin M.; Pande, Vikram; Khetan, Abhishek
- Proceedings of the National Academy of Sciences, Vol. 112, Issue 30
"Water-in-salt" electrolyte enables high-voltage aqueous lithium-ion chemistries
journal, November 2015
- Suo, L.; Borodin, O.; Gao, T.
- Science, Vol. 350, Issue 6263
Electrochemical Properties of Quaternary Ammonium Salts for Electrochemical Capacitors
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The absolute electrode potential: an explanatory note (Recommendations 1986)
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Materials challenges in rechargeable lithium-air batteries
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- Kwabi, D. G.; Ortiz-Vitoriano, N.; Freunberger, S. A.
- MRS Bulletin, Vol. 39, Issue 5