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Title: Effects of Functional Groups in Redox-Active Organic Molecules: A High-Throughput Screening Approach

Nonaqueous redox flow batteries have attracted recent attention with their potential for high electrochemical storage capacity, with organic electrolytes serving as solvents with a wide electrochemical stability window. Organic molecules can also serve as electroactive species, where molecules with low reduction potentials or high oxidation potentials can provide substantial chemical energy. To identify promising electrolytes in a vast chemical space, high-throughput screening (HTS) of candidate molecules plays an important role, where HTS is used to calculate properties of thousands of molecules and identify a few organic molecules worthy of further attention in battery research. Here, in this work, we present reduction and oxidation potentials obtained from HTS of 4178 molecules. The molecules are composed of base groups of five- or six-membered rings with one or two functional groups attached, with the set of possible functional groups including both electron-withdrawing and electron-donating groups. In addition to observing the trends in potentials that result from differences in organic base groups and functional groups, we analyze the effects of molecular characteristics such as multiple bonds, Hammett parameters, and functional group position. In conclusion, this work provides useful guidance in determining how the identities of the base groups and functional groups are correlated withmore » desirable reduction and oxidation potentials.« less
Authors:
ORCiD logo [1] ;  [1] ;  [1]
  1. Argonne National Laboratory (ANL), Lemont, IL (United States). Materials Science Division and Joint Center for Energy Storage Research
Publication Date:
Grant/Contract Number:
AC02-06CH11357; AC02-05CH11231
Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. C
Additional Journal Information:
Journal Volume: 121; Journal Issue: 1; Journal ID: ISSN 1932-7447
Publisher:
American Chemical Society
Research Org:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1352581

Pelzer, Kenley M., Cheng, Lei, and Curtiss, Larry A.. Effects of Functional Groups in Redox-Active Organic Molecules: A High-Throughput Screening Approach. United States: N. p., Web. doi:10.1021/acs.jpcc.6b11473.
Pelzer, Kenley M., Cheng, Lei, & Curtiss, Larry A.. Effects of Functional Groups in Redox-Active Organic Molecules: A High-Throughput Screening Approach. United States. doi:10.1021/acs.jpcc.6b11473.
Pelzer, Kenley M., Cheng, Lei, and Curtiss, Larry A.. 2016. "Effects of Functional Groups in Redox-Active Organic Molecules: A High-Throughput Screening Approach". United States. doi:10.1021/acs.jpcc.6b11473. https://www.osti.gov/servlets/purl/1352581.
@article{osti_1352581,
title = {Effects of Functional Groups in Redox-Active Organic Molecules: A High-Throughput Screening Approach},
author = {Pelzer, Kenley M. and Cheng, Lei and Curtiss, Larry A.},
abstractNote = {Nonaqueous redox flow batteries have attracted recent attention with their potential for high electrochemical storage capacity, with organic electrolytes serving as solvents with a wide electrochemical stability window. Organic molecules can also serve as electroactive species, where molecules with low reduction potentials or high oxidation potentials can provide substantial chemical energy. To identify promising electrolytes in a vast chemical space, high-throughput screening (HTS) of candidate molecules plays an important role, where HTS is used to calculate properties of thousands of molecules and identify a few organic molecules worthy of further attention in battery research. Here, in this work, we present reduction and oxidation potentials obtained from HTS of 4178 molecules. The molecules are composed of base groups of five- or six-membered rings with one or two functional groups attached, with the set of possible functional groups including both electron-withdrawing and electron-donating groups. In addition to observing the trends in potentials that result from differences in organic base groups and functional groups, we analyze the effects of molecular characteristics such as multiple bonds, Hammett parameters, and functional group position. In conclusion, this work provides useful guidance in determining how the identities of the base groups and functional groups are correlated with desirable reduction and oxidation potentials.},
doi = {10.1021/acs.jpcc.6b11473},
journal = {Journal of Physical Chemistry. C},
number = 1,
volume = 121,
place = {United States},
year = {2016},
month = {12}
}