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Title: 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 (S NAr) 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:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [3]; ORCiD logo [1];  [2]; ORCiD logo [4]; ORCiD logo [3]; ORCiD logo [1]
  1. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, USA
  2. Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, USA
  3. Department of Mechanical Engineering, Massachusetts Institute of Technology, Cambridge, USA
  4. Samsung Advanced Institute of Technology (SAIT), Burlington, USA
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (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. doi: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. doi: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 = {2018},
month = {5}
}

Journal Article:
Free Publicly Available Full Text
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DOI: 10.1039/C7EE03509H

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Cited by: 3 works
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    Recent Advances in Electrolytes for Lithium-Sulfur Batteries
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    • Advanced Energy Materials, Vol. 5, Issue 16
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    The future cost of electrical energy storage based on experience rates
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    Single-ion BAB triblock copolymers as highly efficient electrolytes for lithium-metal batteries
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    • Bouchet, Renaud; Maria, Sébastien; Meziane, Rachid
    • Nature Materials, Vol. 12, Issue 5
    • DOI: 10.1038/nmat3602

    Electrolytes for solid-state lithium rechargeable batteries: recent advances and perspectives
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    • DOI: 10.1039/c0cs00081g

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    • Energy & Environmental Science, Vol. 6, Issue 3
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    • DOI: 10.1063/1.449486

    Enhancing electrochemical intermediate solvation through electrolyte anion selection to increase nonaqueous Li–O 2 battery capacity
    journal, July 2015

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    • Proceedings of the National Academy of Sciences, Vol. 112, Issue 30
    • DOI: 10.1073/pnas.1505728112

    "Water-in-salt" electrolyte enables high-voltage aqueous lithium-ion chemistries
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    • DOI: 10.1149/1.1837882

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    Materials challenges in rechargeable lithium-air batteries
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    • Kwabi, D. G.; Ortiz-Vitoriano, N.; Freunberger, S. A.
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