Realization of an Asymmetric Non‐Aqueous Redox Flow Battery through Molecular Design to Minimize Active Species Crossover and Decomposition

Shrestha, Anuska; Hendriks, Koen H.; Sigman, Mathew S.; Minteer, Shelley D.; Sanford, Melanie S.

doi:10.1002/chem.202000749

Realization of an Asymmetric Non‐Aqueous Redox Flow Battery through Molecular Design to Minimize Active Species Crossover and Decomposition

Journal Article · Wed Apr 15 00:00:00 EDT 2020 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.202000749· OSTI ID:1615857

Shrestha, Anuska ^[1]; Hendriks, Koen H. ^[1]; Sigman, Mathew S. ^[2]; Minteer, Shelley D. ^[2]; ^[1]

Joint Center for Energy Storage Research Department of Chemistry University of Michigan 930 North University Avenue Ann Arbor MI 48104 USA
Joint Center for Energy Storage Research Department of Chemistry University of Utah 315 South 1400 East Salt Lake City UT 84112 USA

Abstract

This communication presents a mechanism‐based approach to identify organic electrolytes for non‐aqueous redox flow batteries (RFBs). Symmetrical flow cell cycling of a pyridinium anolyte and a cyclopropenium catholyte resulted in extensive capacity fade due to competing decomposition of the pyridinium species. Characterization of this decomposition pathway enabled the rational design of next‐generation anolyte/catholyte pairs with dramatically enhanced cycling performance. Three factors were identified as critical for slowing capacity fade: (1) separating the anolyte–catholyte in an asymmetric flow cell using an anion exchange membrane (AEM); (2) moving from monomeric to oligomeric electrolytes to limit crossover through the AEM; and (3) removing the basic carbonyl moiety from the anolyte to slow the protonation‐induced decomposition pathway. Ultimately, these modifications led to a novel anolyte–catholyte pair that can be cycled in an AEM‐separated asymmetric RFB for 96 h with >95 % capacity retention at an open circuit voltage of 1.57 V.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

OSTI ID:: 1615857

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 24 Vol. 26; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (59)

Recent Progress in Redox Flow Battery Research and Development Wang, Wei; Luo, Qingtao; Li, Bin Advanced Functional Materials, Vol. 23, Issue 8, p. 970-986 https://doi.org/10.1002/adfm.201200694	journal	September 2012
TEMPO-Based Catholyte for High-Energy Density Nonaqueous Redox Flow Batteries Wei, Xiaoliang; Xu, Wu; Vijayakumar, Murugesan Advanced Materials, Vol. 26, Issue 45 https://doi.org/10.1002/adma.201403746	journal	October 2014
A Two-Electron Storage Nonaqueous Organic Redox Flow Battery Huang, Jinhua; Yang, Zheng; Vijayakumar, Murugesan Advanced Sustainable Systems, Vol. 2, Issue 3 https://doi.org/10.1002/adsu.201700131	journal	February 2018
Cyclopropenium Salts as Cyclable, High-Potential Catholytes in Nonaqueous Media Sevov, Christo S.; Samaroo, Sharmila K.; Sanford, Melanie S. Advanced Energy Materials, Vol. 7, Issue 5 https://doi.org/10.1002/aenm.201602027	journal	November 2016
Annulated Dialkoxybenzenes as Catholyte Materials for Non-aqueous Redox Flow Batteries: Achieving High Chemical Stability through Bicyclic Substitution Zhang, Jingjing; Yang, Zheng; Shkrob, Ilya A. Advanced Energy Materials, Vol. 7, Issue 21 https://doi.org/10.1002/aenm.201701272	journal	July 2017
Die OC(CN)2-Analogie Wallenfels, Kurt; Friedrich, Klaus; Rieser, Jürgen Angewandte Chemie, Vol. 88, Issue 10 https://doi.org/10.1002/ange.19760881003	journal	May 1976
Die Chemie der Redox-Flow-Batterien Noack, Jens; Roznyatovskaya, Nataliya; Herr, Tatjana Angewandte Chemie, Vol. 127, Issue 34 https://doi.org/10.1002/ange.201410823	journal	June 2015
Radical Compatibility with Nonaqueous Electrolytes and Its Impact on an All-Organic Redox Flow Battery Wei, Xiaoliang; Xu, Wu; Huang, Jinhua Angewandte Chemie, Vol. 127, Issue 30 https://doi.org/10.1002/ange.201501443	journal	April 2015
Redox-Flow-Batterien: von metallbasierten zu organischen Aktivmaterialien Winsberg, Jan; Hagemann, Tino; Janoschka, Tobias Angewandte Chemie, Vol. 129, Issue 3 https://doi.org/10.1002/ange.201604925	journal	November 2016
Wasserbasierte Redox-Flow-Batterie mit hoher Kapazität und Leistung: das TEMPTMA/MV-System Janoschka, Tobias; Martin, Norbert; Hager, Martin D. Angewandte Chemie, Vol. 128, Issue 46 https://doi.org/10.1002/ange.201606472	journal	October 2016
Macromolecular Design Strategies for Preventing Active-Material Crossover in Non-Aqueous All-Organic Redox-Flow Batteries Doris, Sean E.; Ward, Ashleigh L.; Baskin, Artem Angewandte Chemie, Vol. 129, Issue 6 https://doi.org/10.1002/ange.201610582	journal	January 2017
Electrochemical Oxidation of Croconate Salts; Evidence of the Chemical Equivalence of the Carbonyl Oxygen Atom and the Dicyanomethylene Group Doane, Lawrence M.; Fatiadi, Alexander J. Angewandte Chemie International Edition in English, Vol. 21, Issue 8 https://doi.org/10.1002/anie.198206351	journal	August 1982
The Chemistry of Redox-Flow Batteries Noack, Jens; Roznyatovskaya, Nataliya; Herr, Tatjana Angewandte Chemie International Edition, Vol. 54, Issue 34 https://doi.org/10.1002/anie.201410823	journal	June 2015
Radical Compatibility with Nonaqueous Electrolytes and Its Impact on an All-Organic Redox Flow Battery Wei, Xiaoliang; Xu, Wu; Huang, Jinhua Angewandte Chemie International Edition, Vol. 54, Issue 30 https://doi.org/10.1002/anie.201501443	journal	April 2015
Redox-Flow Batteries: From Metals to Organic Redox-Active Materials Winsberg, Jan; Hagemann, Tino; Janoschka, Tobias Angewandte Chemie International Edition, Vol. 56, Issue 3 https://doi.org/10.1002/anie.201604925	journal	November 2016
An Aqueous Redox-Flow Battery with High Capacity and Power: The TEMPTMA/MV System Janoschka, Tobias; Martin, Norbert; Hager, Martin D. Angewandte Chemie International Edition, Vol. 55, Issue 46 https://doi.org/10.1002/anie.201606472	journal	October 2016
Macromolecular Design Strategies for Preventing Active-Material Crossover in Non-Aqueous All-Organic Redox-Flow Batteries Doris, Sean E.; Ward, Ashleigh L.; Baskin, Artem Angewandte Chemie International Edition, Vol. 56, Issue 6 https://doi.org/10.1002/anie.201610582	journal	January 2017
Solvent-free Knoevenagel Condensations over TiO2 Hosseini-Sarvari, Mona; Sharghi, Hashem; Etemad, Samane Chinese Journal of Chemistry, Vol. 25, Issue 10 https://doi.org/10.1002/cjoc.200790288	journal	October 2007
Polarographic Properties and Electrochemical Reduction of 1,2-Dimethyl-3-indolyl Heteroaryl Ketones Naef, Rudolf Helvetica Chimica Acta, Vol. 65, Issue 6 https://doi.org/10.1002/hlca.19820650608	journal	September 1982
Comparison of the Strengths of Dicyano-Methylene and Oxygen Acids Rappoport, Z. Israel Journal of Chemistry, Vol. 8, Issue 4 https://doi.org/10.1002/ijch.197000092	journal	January 1970
Theoretical study of electrical and electrochemical properties of cyclopentanepentaone and its dicyanomethylene derivatives Xue, Zhao-Ming; Chen, Chun-Hua International Journal of Quantum Chemistry, Vol. 107, Issue 3 https://doi.org/10.1002/qua.21170	journal	January 2006
Electrochemical properties of a non-aqueous redox battery with all-organic redox couples Park, Se-Kook; Shim, Joonmok; Yang, JungHoon Electrochemistry Communications, Vol. 59 https://doi.org/10.1016/j.elecom.2015.07.013	journal	October 2015
Two electron utilization of methyl viologen anolyte in nonaqueous organic redox flow battery Hu, Bo; Liu, T. Leo Journal of Energy Chemistry, Vol. 27, Issue 5 https://doi.org/10.1016/j.jechem.2018.02.014	journal	September 2018
4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl as a model organic redox active compound for nonaqueous flow batteries Milshtein, Jarrod D.; Barton, John L.; Darling, Robert M. Journal of Power Sources, Vol. 327 https://doi.org/10.1016/j.jpowsour.2016.06.125	journal	September 2016
Application of the dianion croconate violet for symmetric organic non-aqueous redox flow battery electrolytes Armstrong, Craig G.; Hogue, Ross W.; Toghill, Kathryn E. Journal of Power Sources, Vol. 440 https://doi.org/10.1016/j.jpowsour.2019.227037	journal	November 2019
Redox Active Polymers as Soluble Nanomaterials for Energy Storage Burgess, Mark; Moore, Jeffrey S.; Rodríguez-López, Joaquín Accounts of Chemical Research, Vol. 49, Issue 11 https://doi.org/10.1021/acs.accounts.6b00341	journal	September 2016
Poly(boron-dipyrromethene)—A Redox-Active Polymer Class for Polymer Redox-Flow Batteries Winsberg, Jan; Hagemann, Tino; Muench, Simon Chemistry of Materials, Vol. 28, Issue 10 https://doi.org/10.1021/acs.chemmater.6b00640	journal	May 2016
Designing Redox-Active Oligomers for Crossover-Free, Nonaqueous Redox-Flow Batteries with High Volumetric Energy Density Baran, Miranda J.; Braten, Miles N.; Montoto, Elena C. Chemistry of Materials, Vol. 30, Issue 11 https://doi.org/10.1021/acs.chemmater.8b01318	journal	May 2018
Toward Improved Catholyte Materials for Redox Flow Batteries: What Controls Chemical Stability of Persistent Radical Cations? Zhang, Jingjing; Shkrob, Ilya A.; Assary, Rajeev S. The Journal of Physical Chemistry C, Vol. 121, Issue 42 https://doi.org/10.1021/acs.jpcc.7b08281	journal	October 2017
Symmetric All-Quinone Aqueous Battery Tong, Liuchuan; Jing, Yan; Gordon, Roy G. ACS Applied Energy Materials, Vol. 2, Issue 6 https://doi.org/10.1021/acsaem.9b00691	journal	May 2019
High-Performance Oligomeric Catholytes for Effective Macromolecular Separation in Nonaqueous Redox Flow Batteries Hendriks, Koen H.; Robinson, Sophia G.; Braten, Miles N. ACS Central Science, Vol. 4, Issue 2 https://doi.org/10.1021/acscentsci.7b00544	journal	January 2018
A High-Current, Stable Nonaqueous Organic Redox Flow Battery Wei, Xiaoliang; Duan, Wentao; Huang, Jinhua ACS Energy Letters, Vol. 1, Issue 4 https://doi.org/10.1021/acsenergylett.6b00255	journal	September 2016
“Wine-Dark Sea” in an Organic Flow Battery: Storing Negative Charge in 2,1,3-Benzothiadiazole Radicals Leads to Improved Cyclability Duan, Wentao; Huang, Jinhua; Kowalski, Jeffrey A. ACS Energy Letters, Vol. 2, Issue 5 https://doi.org/10.1021/acsenergylett.7b00261	journal	April 2017
Redox Flow Batteries Kamat, Prashant V.; Schanze, Kirk S.; Buriak, Jillian M. ACS Energy Letters, Vol. 2, Issue 6 https://doi.org/10.1021/acsenergylett.7b00361	journal	May 2017
Materials and Systems for Organic Redox Flow Batteries: Status and Challenges Wei, Xiaoliang; Pan, Wenxiao; Duan, Wentao ACS Energy Letters, Vol. 2, Issue 9 https://doi.org/10.1021/acsenergylett.7b00650	journal	August 2017
Molecular Engineering of an Alkaline Naphthoquinone Flow Battery Tong, Liuchuan; Goulet, Marc-Antoni; Tabor, Daniel P. ACS Energy Letters, Vol. 4, Issue 8 https://doi.org/10.1021/acsenergylett.9b01321	journal	July 2019
Flow Batteries: Current Status and Trends Soloveichik, Grigorii L. Chemical Reviews, Vol. 115, Issue 20 https://doi.org/10.1021/cr500720t	journal	September 2015
Long-Cycling Aqueous Organic Redox Flow Battery (AORFB) toward Sustainable and Safe Energy Storage Hu, Bo; DeBruler, Camden; Rhodes, Zayn Journal of the American Chemical Society, Vol. 139, Issue 3 https://doi.org/10.1021/jacs.6b10984	journal	January 2017
Physical Organic Approach to Persistent, Cyclable, Low-Potential Electrolytes for Flow Battery Applications Sevov, Christo S.; Hickey, David P.; Cook, Monique E. Journal of the American Chemical Society, Vol. 139, Issue 8 https://doi.org/10.1021/jacs.7b00147	journal	February 2017
Extending the Lifetime of Organic Flow Batteries via Redox State Management Goulet, Marc-Antoni; Tong, Liuchuan; Pollack, Daniel A. Journal of the American Chemical Society https://doi.org/10.1021/jacs.8b13295	journal	April 2019
Developing a Predictive Solubility Model for Monomeric and Oligomeric Cyclopropenium-Based Flow Battery Catholytes Robinson, Sophia G.; Yan, Yichao; Hendriks, Koen H. Journal of the American Chemical Society, Vol. 141, Issue 26 https://doi.org/10.1021/jacs.9b04270	journal	May 2019
Mechanism-Based Design of a High-Potential Catholyte Enables a 3.2 V All-Organic Nonaqueous Redox Flow Battery Yan, Yichao; Robinson, Sophia G.; Sigman, Matthew S. Journal of the American Chemical Society, Vol. 141, Issue 38 https://doi.org/10.1021/jacs.9b07345	journal	September 2019
The Redox Chemistry of 4-Benzoyl- N- methylpyridinium Cations in Acetonitrile with and without Proton Donors: The Role of Hydrogen Bonding Leventis, Nicholas; Elder, Ian A.; Gao, Xuerong The Journal of Physical Chemistry B, Vol. 105, Issue 17 https://doi.org/10.1021/jp0107199	journal	May 2001
A metal-free organic–inorganic aqueous flow battery Huskinson, Brian; Marshak, Michael P.; Suh, Changwon Nature, Vol. 505, Issue 7482, p. 195-198 https://doi.org/10.1038/nature12909	journal	January 2014
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
Redox flow batteries go organic Wang, Wei; Sprenkle, Vince Nature Chemistry, Vol. 8, Issue 3 https://doi.org/10.1038/nchem.2466	journal	February 2016
A redox-flow battery with an alloxazine-based organic electrolyte Lin, Kaixiang; Gómez-Bombarelli, Rafael; Beh, Eugene S. Nature Energy, Vol. 1, Issue 9 https://doi.org/10.1038/nenergy.2016.102	journal	July 2016
Structure–property relationship of donor–acceptor acridones – an optical, electrochemical and computational study Thériault, K. D.; Radford, C.; Parvez, M. Physical Chemistry Chemical Physics, Vol. 17, Issue 32 https://doi.org/10.1039/C5CP03222A	journal	January 2015
The rise of organic electrode materials for energy storage Schon, Tyler B.; McAllister, Bryony T.; Li, Peng-Fei Chemical Society Reviews, Vol. 45, Issue 22 https://doi.org/10.1039/C6CS00173D	journal	January 2016
High current density, long duration cycling of soluble organic active species for non-aqueous redox flow batteries Milshtein, Jarrod D.; Kaur, Aman Preet; Casselman, Matthew D. Energy & Environmental Science, Vol. 9, Issue 11 https://doi.org/10.1039/C6EE02027E	journal	January 2016
A high-performance all-metallocene-based, non-aqueous redox flow battery Ding, Yu; Zhao, Yu; Li, Yutao Energy & Environmental Science, Vol. 10, Issue 2 https://doi.org/10.1039/C6EE02057G	journal	January 2017
Review of electrical energy storage technologies, materials and systems: challenges and prospects for large-scale grid storage Gür, Turgut M. Energy & Environmental Science, Vol. 11, Issue 10 https://doi.org/10.1039/C8EE01419A	journal	January 2018
Substituted thiadiazoles as energy-rich anolytes for nonaqueous redox flow cells Huang, Jinhua; Duan, Wentao; Zhang, Jingjing Journal of Materials Chemistry A, Vol. 6, Issue 15 https://doi.org/10.1039/C8TA01059E	journal	January 2018
Electricity storage for intermittent renewable sources Rugolo, Jason; Aziz, Michael J. Energy & Environmental Science, Vol. 5, Issue 5 https://doi.org/10.1039/c2ee02542f	journal	January 2012
A review of current developments in non-aqueous redox flow batteries: characterization of their membranes for design perspective Shin, Sung-Hee; Yun, Sung-Hyun; Moon, Seung-Hyeon RSC Advances, Vol. 3, Issue 24, p. 9095-9116 https://doi.org/10.1039/c3ra00115f	journal	January 2013
Cycling Analysis of a Quinone-Bromide Redox Flow Battery Chen, Qing; Eisenach, Louise; Aziz, Michael J. Journal of The Electrochemical Society, Vol. 163, Issue 1 https://doi.org/10.1149/2.0081601jes	journal	September 2015
Electrolyte Development for Non-Aqueous Redox Flow Batteries Using a High-Throughput Screening Platform Su, Liang; Ferrandon, Magali; Kowalski, Jeffrey A. Journal of The Electrochemical Society, Vol. 161, Issue 12 https://doi.org/10.1149/2.0811412jes	journal	January 2014
Redox Active Polymers for Non-Aqueous Redox Flow Batteries: Validation of the Size-Exclusion Approach Montoto, Elena C.; Nagarjuna, Gavvalapalli; Moore, Jeffrey S. Journal of The Electrochemical Society, Vol. 164, Issue 7 https://doi.org/10.1149/2.1511707jes	journal	January 2017
Comparison of Capacity Retention Rates During Cycling of Quinone-Bromide Flow Batteries Gerhardt, Michael R.; Beh, Eugene S.; Tong, Liuchuan MRS Advances, Vol. 2, Issue 8 https://doi.org/10.1557/adv.2016.667	journal	December 2016

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