Design of S-Substituted Fluorinated Aryl Sulfonamide-Tagged (S-FAST) Anions to Enable New Solvate Ionic Liquids for Battery Applications

Mingjun Huang; Shuting Feng; Wenxu Zhang; Jeffrey Lopez; Bo Qiao; Ryoichi Tatara; Livia Giordano; Yang Shao-Horn; Jeremiah A. Johnson

doi:10.1021/acs.chemmater.9b02353

Design of S-Substituted Fluorinated Aryl Sulfonamide-Tagged (S-FAST) Anions to Enable New Solvate Ionic Liquids for Battery Applications

Mingjun Huang, Shuting Feng, Wenxu Zhang, Jeffrey Lopez, Bo Qiao, Ryoichi Tatara, Livia Giordano, Yang Shao-Horn^*, Jeremiah A. Johnson

^*Corresponding author for this work

Chemical and Biological Engineering

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

Electrolytes with improved thermal and oxidative stability must be developed to achieve greater power and energy densities without compromising safety in modern energy storage devices. Because of their much-reduced solvent vapor pressure and expanded electrochemical windows, solvate ionic liquids (SILs) of lithium salts have recently attracted significant attention in this regard. The current palette of SILs is, however, limited to only a few suitable anions with limited chemical functionality. Guided by fundamental physical organic chemistry principles, we designed a new family of S-substituted fluorinated aryl sulfonamide-tagged anions that feature variable numbers of electronically neutral or withdrawing sulfide, sulfoxide, and sulfone substituents. Several salts of these electron deficient anions display very high electrochemical oxidative stability, good solubility, and a weakly coordinating nature that enables the synthesis of Li-based SILs with high thermal and electrochemical oxidative stability. This new family of functional, noncoordinating anions will potentially expand the scope of applications of SILs as safe electrolytes in battery devices.

Original language	English (US)
Pages (from-to)	7558-7564
Number of pages	7
Journal	Chemistry of Materials
Volume	31
Issue number	18
DOIs	https://doi.org/10.1021/acs.chemmater.9b02353
State	Published - Sep 24 2019

Funding

The authors acknowledge the Samsung Advanced Institute of Technology (SAIT) for funding this research. S.F. gratefully acknowledges the Link Foundation for the Link Energy Fellowship. This research used the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by National Science Foundation Grant ACI-1548562. J.L. gratefully acknowledges support by an appointment to the Intelligence Community Postdoctoral Research Fellowship Program at the Massachusetts Institute of Technology, administered by the Oak Ridge Institute for Science and Education through an interagency agreement between the U.S. Department of Energy and the Office of the Director of National Intelligence.

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

Access to Document

10.1021/acs.chemmater.9b02353

Cite this

@article{1f016c0676a348e1ad3120dd30b94482,

title = "Design of S-Substituted Fluorinated Aryl Sulfonamide-Tagged (S-FAST) Anions to Enable New Solvate Ionic Liquids for Battery Applications",

abstract = "Electrolytes with improved thermal and oxidative stability must be developed to achieve greater power and energy densities without compromising safety in modern energy storage devices. Because of their much-reduced solvent vapor pressure and expanded electrochemical windows, solvate ionic liquids (SILs) of lithium salts have recently attracted significant attention in this regard. The current palette of SILs is, however, limited to only a few suitable anions with limited chemical functionality. Guided by fundamental physical organic chemistry principles, we designed a new family of S-substituted fluorinated aryl sulfonamide-tagged anions that feature variable numbers of electronically neutral or withdrawing sulfide, sulfoxide, and sulfone substituents. Several salts of these electron deficient anions display very high electrochemical oxidative stability, good solubility, and a weakly coordinating nature that enables the synthesis of Li-based SILs with high thermal and electrochemical oxidative stability. This new family of functional, noncoordinating anions will potentially expand the scope of applications of SILs as safe electrolytes in battery devices.",

author = "Mingjun Huang and Shuting Feng and Wenxu Zhang and Jeffrey Lopez and Bo Qiao and Ryoichi Tatara and Livia Giordano and Yang Shao-Horn and Johnson, \{Jeremiah A.\}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = sep,

day = "24",

doi = "10.1021/acs.chemmater.9b02353",

language = "English (US)",

volume = "31",

pages = "7558--7564",

journal = "Chemistry of Materials",

issn = "0897-4756",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Design of S-Substituted Fluorinated Aryl Sulfonamide-Tagged (S-FAST) Anions to Enable New Solvate Ionic Liquids for Battery Applications

AU - Huang, Mingjun

AU - Feng, Shuting

AU - Zhang, Wenxu

AU - Lopez, Jeffrey

AU - Qiao, Bo

AU - Tatara, Ryoichi

AU - Giordano, Livia

AU - Shao-Horn, Yang

AU - Johnson, Jeremiah A.

PY - 2019/9/24

Y1 - 2019/9/24

N2 - Electrolytes with improved thermal and oxidative stability must be developed to achieve greater power and energy densities without compromising safety in modern energy storage devices. Because of their much-reduced solvent vapor pressure and expanded electrochemical windows, solvate ionic liquids (SILs) of lithium salts have recently attracted significant attention in this regard. The current palette of SILs is, however, limited to only a few suitable anions with limited chemical functionality. Guided by fundamental physical organic chemistry principles, we designed a new family of S-substituted fluorinated aryl sulfonamide-tagged anions that feature variable numbers of electronically neutral or withdrawing sulfide, sulfoxide, and sulfone substituents. Several salts of these electron deficient anions display very high electrochemical oxidative stability, good solubility, and a weakly coordinating nature that enables the synthesis of Li-based SILs with high thermal and electrochemical oxidative stability. This new family of functional, noncoordinating anions will potentially expand the scope of applications of SILs as safe electrolytes in battery devices.

AB - Electrolytes with improved thermal and oxidative stability must be developed to achieve greater power and energy densities without compromising safety in modern energy storage devices. Because of their much-reduced solvent vapor pressure and expanded electrochemical windows, solvate ionic liquids (SILs) of lithium salts have recently attracted significant attention in this regard. The current palette of SILs is, however, limited to only a few suitable anions with limited chemical functionality. Guided by fundamental physical organic chemistry principles, we designed a new family of S-substituted fluorinated aryl sulfonamide-tagged anions that feature variable numbers of electronically neutral or withdrawing sulfide, sulfoxide, and sulfone substituents. Several salts of these electron deficient anions display very high electrochemical oxidative stability, good solubility, and a weakly coordinating nature that enables the synthesis of Li-based SILs with high thermal and electrochemical oxidative stability. This new family of functional, noncoordinating anions will potentially expand the scope of applications of SILs as safe electrolytes in battery devices.

UR - http://www.scopus.com/inward/record.url?scp=85072317546&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85072317546&partnerID=8YFLogxK

U2 - 10.1021/acs.chemmater.9b02353

DO - 10.1021/acs.chemmater.9b02353

M3 - Article

AN - SCOPUS:85072317546

SN - 0897-4756

VL - 31

SP - 7558

EP - 7564

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 18

ER -

Design of S-Substituted Fluorinated Aryl Sulfonamide-Tagged (S-FAST) Anions to Enable New Solvate Ionic Liquids for Battery Applications

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this