Fluorinated Aryl Sulfonimide Tagged (FAST) salts: modular synthesis and structure–property relationships for battery applications

Huang, Mingjun; Feng, Shuting; Zhang, Wenxu; Giordano, Livia; Chen, Mao; Amanchukwu, Chibueze V.; Anandakathir, Robinson; Shao-Horn, Yang; Johnson, Jeremiah A.

doi:10.1039/C7EE03509H

Title: Fluorinated Aryl Sulfonimide Tagged (FAST) salts: modular synthesis and structure–property relationships for battery applications

Journal Article · Wed May 16 00:00:00 EDT 2018 · Energy & Environmental Science

DOI:https://doi.org/10.1039/C7EE03509H· OSTI ID:1483900

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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

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.

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

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC02-5CH11231; AC02-05CH11231

OSTI ID:: 1483900

Alternate ID(s):: OSTI ID: 1434114; OSTI ID: 1543790

Journal Information:: Energy & Environmental Science, Journal Name: Energy & Environmental Science Vol. 11 Journal Issue: 5; ISSN 1754-5692

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 20 works

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Lithium-Sulfur Batteries: Progress and Prospects Manthiram, Arumugam; Chung, Sheng-Heng; Zu, Chenxi Advanced Materials, Vol. 27, Issue 12 https://doi.org/10.1002/adma.201405115	journal	February 2015
Effect of Molecular Weight and Salt Concentration on Ion Transport and the Transference Number in Polymer Electrolytes Timachova, Ksenia; Watanabe, Hiroshi; Balsara, Nitash P. Macromolecules, Vol. 48, Issue 21 https://doi.org/10.1021/acs.macromol.5b01724	journal	October 2015
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Understanding the Chemical Stability of Polymers for Lithium–Air Batteries Amanchukwu, Chibueze V.; Harding, Jonathon R.; Shao-Horn, Yang Chemistry of Materials, Vol. 27, Issue 2 https://doi.org/10.1021/cm5040003	journal	January 2015
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Synthesis and characterization of a new family of aryl-trifluoromethanesulfonylimide Li-Salts for Li-ion batteries and beyond Ladouceur, Sébastien; Paillet, Sabrina; Vijh, Ashok Journal of Power Sources, Vol. 293 https://doi.org/10.1016/j.jpowsour.2015.05.011	journal	October 2015
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Lithium battery chemistries enabled by solid-state electrolytes Manthiram, Arumugam; Yu, Xingwen; Wang, Shaofei Nature Reviews Materials, Vol. 2, Issue 4 https://doi.org/10.1038/natrevmats.2016.103	journal	February 2017
Enhancing electrochemical intermediate solvation through electrolyte anion selection to increase nonaqueous Li–O ₂ battery capacity Burke, Colin M.; Pande, Vikram; Khetan, Abhishek Proceedings of the National Academy of Sciences, Vol. 112, Issue 30 https://doi.org/10.1073/pnas.1505728112	journal	July 2015
Single Lithium-Ion Conducting Polymer Electrolytes Based on a Super-Delocalized Polyanion Ma, Qiang; Zhang, Heng; Zhou, Chongwang Angewandte Chemie, Vol. 128, Issue 7 https://doi.org/10.1002/ange.201509299	journal	January 2016

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Lithium-Sulfur Batteries: Progress and Prospects Manthiram, Arumugam; Chung, Sheng-Heng; Zu, Chenxi Advanced Materials, Vol. 27, Issue 12 https://doi.org/10.1002/adma.201405115	journal	February 2015
Recent Advances in Electrolytes for Lithium-Sulfur Batteries Zhang, Shiguo; Ueno, Kazuhide; Dokko, Kaoru Advanced Energy Materials, Vol. 5, Issue 16 https://doi.org/10.1002/aenm.201500117	journal	April 2015
Lithium-Sulfur Batteries: Electrochemistry, Materials, and Prospects Yin, Ya-Xia; Xin, Sen; Guo, Yu-Guo Angewandte Chemie International Edition, Vol. 52, Issue 50 https://doi.org/10.1002/anie.201304762	journal	November 2013
Single Lithium-Ion Conducting Polymer Electrolytes Based on a Super-Delocalized Polyanion Ma, Qiang; Zhang, Heng; Zhou, Chongwang Angewandte Chemie International Edition, Vol. 55, Issue 7 https://doi.org/10.1002/anie.201509299	journal	January 2016
Concentrated Electrolyte for the Sodium-Oxygen Battery: Solvation Structure and Improved Cycle Life He, Mingfu; Lau, Kah Chun; Ren, Xiaodi Angewandte Chemie International Edition, Vol. 55, Issue 49 https://doi.org/10.1002/anie.201608607	journal	November 2016
Gutmann Donor and Acceptor Numbers for Ionic Liquids Schmeisser, Matthias; Illner, Peter; Puchta, Ralph Chemistry - A European Journal, Vol. 18, Issue 35 https://doi.org/10.1002/chem.201200584	journal	July 2012
The electrochemistry of noble metal electrodes in aprotic organic solvents containing lithium salts Aurbach, D.; Daroux, M.; Faguy, P. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 297, Issue 1 https://doi.org/10.1016/0022-0728(91)85370-5	journal	January 1991
Investigations on the electrochemical performance and thermal stability of two new lithium electrolyte salts in comparison to LiPF6 Murmann, Patrick; Niehoff, Philip; Schmitz, René Electrochimica Acta, Vol. 114 https://doi.org/10.1016/j.electacta.2013.09.155	journal	December 2013
A novel and efficient method for the synthesis of polyfluoroarenesulfonyl bromides from polyfluoroarenethiols Platonov, Vyacheslav E.; Bredikhin, Roman A.; Maksimov, Alexander M. Journal of Fluorine Chemistry, Vol. 131, Issue 1 https://doi.org/10.1016/j.jfluchem.2009.09.011	journal	January 2010
Synthesis and characterization of a new family of aryl-trifluoromethanesulfonylimide Li-Salts for Li-ion batteries and beyond Ladouceur, Sébastien; Paillet, Sabrina; Vijh, Ashok Journal of Power Sources, Vol. 293 https://doi.org/10.1016/j.jpowsour.2015.05.011	journal	October 2015
Li-ion battery materials: present and future Nitta, Naoki; Wu, Feixiang; Lee, Jung Tae Materials Today, Vol. 18, Issue 5 https://doi.org/10.1016/j.mattod.2014.10.040	journal	June 2015
Computational Design of New Magnesium Electrolytes with Improved Properties Qu, Xiaohui; Zhang, Yong; Rajput, Nav Nidhi The Journal of Physical Chemistry C, Vol. 121, Issue 30 https://doi.org/10.1021/acs.jpcc.7b04516	journal	July 2017
Effect of Molecular Weight and Salt Concentration on Ion Transport and the Transference Number in Polymer Electrolytes Timachova, Ksenia; Watanabe, Hiroshi; Balsara, Nitash P. Macromolecules, Vol. 48, Issue 21 https://doi.org/10.1021/acs.macromol.5b01724	journal	October 2015
Dependence of Morphology, Shear Modulus, and Conductivity on the Composition of Lithiated and Magnesiated Single-Ion-Conducting Block Copolymer Electrolytes Rojas, Adriana A.; Thakker, Kanav; McEntush, Kyle D. Macromolecules, Vol. 50, Issue 21 https://doi.org/10.1021/acs.macromol.7b01686	journal	October 2017
Single-Ion Conducting Polymer Electrolytes for Lithium Metal Polymer Batteries that Operate at Ambient Temperature Porcarelli, Luca; Shaplov, Alexander S.; Bella, Federico ACS Energy Letters, Vol. 1, Issue 4 https://doi.org/10.1021/acsenergylett.6b00216	journal	September 2016
Promising Routes to a High Li ⁺ Transference Number Electrolyte for Lithium Ion Batteries Diederichsen, Kyle M.; McShane, Eric J.; McCloskey, Bryan D. ACS Energy Letters, Vol. 2, Issue 11 https://doi.org/10.1021/acsenergylett.7b00792	journal	October 2017
Understanding the Chemical Stability of Polymers for Lithium–Air Batteries Amanchukwu, Chibueze V.; Harding, Jonathon R.; Shao-Horn, Yang Chemistry of Materials, Vol. 27, Issue 2 https://doi.org/10.1021/cm5040003	journal	January 2015
Nonaqueous Liquid Electrolytes for Lithium-Based Rechargeable Batteries Xu, Kang Chemical Reviews, Vol. 104, Issue 10, p. 4303-4418 https://doi.org/10.1021/cr030203g	journal	October 2004
Electrolytes and Interphases in Li-Ion Batteries and Beyond Xu, Kang Chemical Reviews, Vol. 114, Issue 23 https://doi.org/10.1021/cr500003w	journal	October 2014
Nonaqueous Li–Air Batteries: A Status Report Luntz, Alan C.; McCloskey, Bryan D. Chemical Reviews, Vol. 114, Issue 23 https://doi.org/10.1021/cr500054y	journal	October 2014
Natural hybrid orbitals Foster, J. P.; Weinhold, F. Journal of the American Chemical Society, Vol. 102, Issue 24 https://doi.org/10.1021/ja00544a007	journal	September 1980
Spectroscopic studies of ionic solvation. X. Study of the solvation of sodium ions in nonaqueous solvents by sodium-23 nuclear magnetic resonance Erlich, Ronald H.; Popov, Alexander I. Journal of the American Chemical Society, Vol. 93, Issue 22 https://doi.org/10.1021/ja00751a005	journal	November 1971
Reactions in the Rechargeable Lithium–O ₂ Battery with Alkyl Carbonate Electrolytes Freunberger, Stefan A.; Chen, Yuhui; Peng, Zhangquan Journal of the American Chemical Society, Vol. 133, Issue 20 https://doi.org/10.1021/ja2021747	journal	May 2011
Density Functional Theory Study of the Role of Anions on the Oxidative Decomposition Reaction of Propylene Carbonate Xing, Lidan; Borodin, Oleg; Smith, Grant D. The Journal of Physical Chemistry A, Vol. 115, Issue 47 https://doi.org/10.1021/jp206153n	journal	December 2011
Instability of Poly(ethylene oxide) upon Oxidation in Lithium–Air Batteries Harding, Jonathon R.; Amanchukwu, Chibueze V.; Hammond, Paula T. The Journal of Physical Chemistry C, Vol. 119, Issue 13 https://doi.org/10.1021/jp511794g	journal	March 2015
Issues and challenges facing rechargeable lithium batteries Tarascon, J.-M.; Armand, M. Nature, Vol. 414, Issue 6861, p. 359-367 https://doi.org/10.1038/35104644	journal	November 2001
Lithium battery chemistries enabled by solid-state electrolytes Manthiram, Arumugam; Yu, Xingwen; Wang, Shaofei Nature Reviews Materials, Vol. 2, Issue 4 https://doi.org/10.1038/natrevmats.2016.103	journal	February 2017
Opportunities and challenges for a sustainable energy future Chu, Steven; Majumdar, Arun Nature, Vol. 488, Issue 7411, p. 294-303 https://doi.org/10.1038/nature11475	journal	August 2012
Towards greener and more sustainable batteries for electrical energy storage Larcher, D.; Tarascon, J-M. Nature Chemistry, Vol. 7, Issue 1 https://doi.org/10.1038/nchem.2085	journal	November 2014
Advances in understanding mechanisms underpinning lithium–air batteries Aurbach, Doron; McCloskey, Bryan D.; Nazar, Linda F. Nature Energy, Vol. 1, Issue 9 https://doi.org/10.1038/nenergy.2016.128	journal	September 2016
Advances in lithium–sulfur batteries based on multifunctional cathodes and electrolytes Pang, Quan; Liang, Xiao; Kwok, Chun Yuen Nature Energy, Vol. 1, Issue 9 https://doi.org/10.1038/nenergy.2016.132	journal	September 2016
The future cost of electrical energy storage based on experience rates Schmidt, O.; Hawkes, A.; Gambhir, A. Nature Energy, Vol. 2, Issue 8 https://doi.org/10.1038/nenergy.2017.110	journal	July 2017
Single-ion BAB triblock copolymers as highly efficient electrolytes for lithium-metal batteries Bouchet, Renaud; Maria, Sébastien; Meziane, Rachid Nature Materials, Vol. 12, Issue 5 https://doi.org/10.1038/nmat3602	journal	March 2013
Electrolytes for solid-state lithium rechargeable batteries: recent advances and perspectives Quartarone, Eliana; Mustarelli, Piercarlo Chemical Society Reviews, Vol. 40, Issue 5 https://doi.org/10.1039/c0cs00081g	journal	January 2011
Lithium–oxygen batteries: bridging mechanistic understanding and battery performance Lu, Yi-Chun; Gallant, Betar M.; Kwabi, David G. Energy & Environmental Science, Vol. 6, Issue 3 https://doi.org/10.1039/c3ee23966g	journal	January 2013
Natural population analysis Reed, Alan E.; Weinstock, Robert B.; Weinhold, Frank The Journal of Chemical Physics, Vol. 83, Issue 2 https://doi.org/10.1063/1.449486	journal	July 1985
Enhancing electrochemical intermediate solvation through electrolyte anion selection to increase nonaqueous Li–O ₂ battery capacity Burke, Colin M.; Pande, Vikram; Khetan, Abhishek Proceedings of the National Academy of Sciences, Vol. 112, Issue 30 https://doi.org/10.1073/pnas.1505728112	journal	July 2015
"Water-in-salt" electrolyte enables high-voltage aqueous lithium-ion chemistries Suo, L.; Borodin, O.; Gao, T. Science, Vol. 350, Issue 6263 https://doi.org/10.1126/science.aab1595	journal	November 2015
Electrochemical Properties of Quaternary Ammonium Salts for Electrochemical Capacitors Ue, Makoto Journal of The Electrochemical Society, Vol. 144, Issue 8 https://doi.org/10.1149/1.1837882	journal	January 1997
The absolute electrode potential: an explanatory note (Recommendations 1986) Trasatti, S. Pure and Applied Chemistry, Vol. 58, Issue 7 https://doi.org/10.1351/pac198658070955	journal	January 1986
Materials challenges in rechargeable lithium-air batteries Kwabi, D. G.; Ortiz-Vitoriano, N.; Freunberger, S. A. MRS Bulletin, Vol. 39, Issue 5 https://doi.org/10.1557/mrs.2014.87	journal	May 2014

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