Comparison of Quinone‐Based Catholytes for Aqueous Redox Flow Batteries and Demonstration of Long‐Term Stability with Tetrasubstituted Quinones

Gerken, James B.; Anson, Colin W.; Preger, Yuliya; Symons, Peter G.; Genders, J. David; Qiu, Yang; Li, Wenzhen; Root, Thatcher W.; Stahl, Shannon S.

doi:10.1002/aenm.202000340

Comparison of Quinone‐Based Catholytes for Aqueous Redox Flow Batteries and Demonstration of Long‐Term Stability with Tetrasubstituted Quinones

Journal Article · Wed Apr 15 00:00:00 EDT 2020 · Advanced Energy Materials

DOI:https://doi.org/10.1002/aenm.202000340· OSTI ID:1615062

Gerken, James B. ^[1]; ^[1]; ^[2]; Symons, Peter G. ^[3]; Genders, J. David ^[3]; Qiu, Yang ^[4]; Li, Wenzhen ^[4]; Root, Thatcher W. ^[2]; ^[1]

Department of Chemistry University of Wisconsin–Madison 1101 University Avenue Madison WI 53706‐1322 USA
Department of Chemical and Biological Engineering University of Wisconsin–Madison 1415 Engineering Drive Madison WI 53706 USA
Electrosynthesis Company, Inc 72 Ward Road Lancaster NY 14086 USA
Department of Chemical and Biological Engineering Iowa State University 2114 Sweeney Hall, 618 Bissell Road Ames IA 50011‐2230 USA

Abstract

Quinones are appealing targets as organic charge carriers for aqueous redox flow batteries (RFBs), but their utility continues to be constrained by limited stability under operating conditions. The present study evaluates the stability of a series of water‐soluble quinones, with redox potentials ranging from 605–885 mV versus NHE, under acidic aqueous conditions (1 m H ₂ SO ₄ ). Four of the quinones are examined as cathodic electrolytes in an aqueous RFB, paired with anthraquinone‐2,7‐disulfonate as the anodic electrolyte. The RFB data complement other solution stability tests and show that the most stable electrolyte is a tetrasubstituted quinone containing four sulfonated thioether substituents. The results highlight the importance of substituting all C–H positions of the quinone in order to maximize the quinone stability and set the stage for design of improved organic electrolytes for aqueous RFBs.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

OSTI ID:: 1615062

Alternate ID(s):: OSTI ID: 1706729

Journal Information:: Advanced Energy Materials, Journal Name: Advanced Energy Materials Journal Issue: 20 Vol. 10; ISSN 1614-6832

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

Country of Publication:: Germany

Language:: English

References (36)

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
A pH‐Neutral, Metal‐Free Aqueous Organic Redox Flow Battery Employing an Ammonium Anthraquinone Anolyte Hu, Bo; Luo, Jian; Hu, Maowei Angewandte Chemie International Edition, Vol. 58, Issue 46 https://doi.org/10.1002/anie.201907934	journal	November 2019
Which Parameter is Governing for Aqueous Redox Flow Batteries with Organic Active Material? Hofmann, Jonas D.; Schröder, Daniel Chemie Ingenieur Technik, Vol. 91, Issue 6 https://doi.org/10.1002/cite.201800162	journal	March 2019
The acid-catalysed oligomerisation of p-benzoquinone Erdtman, Holger; Högberg, Hans-Erik Tetrahedron, Vol. 35, Issue 4 https://doi.org/10.1016/0040-4020(79)80152-0	journal	January 1979
Utilization of industrial waste liquors from the production of sulphonated derivatives of anthraquinone Socha, Adam Dyes and Pigments, Vol. 12, Issue 3 https://doi.org/10.1016/0143-7208(90)85013-E	journal	January 1990
An Organic Electroactive Material for Flow Batteries Zhang, Shu; Li, Xin; Chu, Dandan Electrochimica Acta, Vol. 190 https://doi.org/10.1016/j.electacta.2015.12.139	journal	February 2016
Vanadium, recent advancements and research prospects: A review Imtiaz, Muhammad; Rizwan, Muhammad Shahid; Xiong, Shuanglian Environment International, Vol. 80 https://doi.org/10.1016/j.envint.2015.03.018	journal	July 2015
Quinone-Mediated Electrochemical O2 Reduction Accessing High Power Density with an Off-Electrode Co-N/C Catalyst Preger, Yuliya; Gerken, James B.; Biswas, Sourav Joule, Vol. 2, Issue 12 https://doi.org/10.1016/j.joule.2018.09.010	journal	December 2018
Recent developments in organic redox flow batteries: A critical review Leung, P.; Shah, A. A.; Sanz, L. Journal of Power Sources, Vol. 360 https://doi.org/10.1016/j.jpowsour.2017.05.057	journal	August 2017
Bio-Inspired Electroactive Organic Molecules for Aqueous Redox Flow Batteries. 1. Thiophenoquinones Pineda Flores, Sergio D.; Martin-Noble, Geoffrey C.; Phillips, Richard L. The Journal of Physical Chemistry C, Vol. 119, Issue 38 https://doi.org/10.1021/acs.jpcc.5b05346	journal	September 2015
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
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
Status and Prospects of Organic Redox Flow Batteries toward Sustainable Energy Storage Luo, Jian; Hu, Bo; Hu, Maowei ACS Energy Letters, Vol. 4, Issue 9 https://doi.org/10.1021/acsenergylett.9b01332	journal	August 2019
Electrochemical Energy Storage for Green Grid Yang, Zhenguo; Zhang, Jianlu; Kintner-Meyer, Michael C. W. Chemical Reviews, Vol. 111, Issue 5, p. 3577-3613 https://doi.org/10.1021/cr100290v	journal	May 2011
Flow Batteries: Current Status and Trends Soloveichik, Grigorii L. Chemical Reviews, Vol. 115, Issue 20 https://doi.org/10.1021/cr500720t	journal	September 2015
The Chemistry of Anthraquinone. Phillips, Max. Chemical Reviews, Vol. 6, Issue 1 https://doi.org/10.1021/cr60021a007	journal	April 1929
Oxidation Processes. XIII. ¹ The Inhibitory Action of Sulfite and other Compounds in the Autoxidation of Hydroquinone and its Homologs James, T. H.; Weissberger, A. Journal of the American Chemical Society, Vol. 61, Issue 2 https://doi.org/10.1021/ja01871a064	journal	February 1939
Quinone 1 e ^– and 2 e ^– /2 H ⁺ Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships Huynh, Mioy T.; Anson, Colin W.; Cavell, Andrew C. Journal of the American Chemical Society, Vol. 138, Issue 49 https://doi.org/10.1021/jacs.6b05797	journal	November 2016
Novel Catalysis of Hydroquinone Autoxidation with Nitrogen Oxides Bosch, E.; Rathore, R.; Kochi, J. K. The Journal of Organic Chemistry, Vol. 59, Issue 9 https://doi.org/10.1021/jo00088a039	journal	May 1994
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
A biomimetic high-capacity phenazine-based anolyte for aqueous organic redox flow batteries Hollas, Aaron; Wei, Xiaoliang; Murugesan, Vijayakumar Nature Energy, Vol. 3, Issue 6 https://doi.org/10.1038/s41560-018-0167-3	journal	June 2018
Organic Redox Species in Aqueous Flow Batteries: Redox Potentials, Chemical Stability and Solubility Wedege, Kristina; Dražević, Emil; Konya, Denes Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep39101	journal	December 2016
Computational design of molecules for an all-quinone redox flow battery Er, Süleyman; Suh, Changwon; Marshak, Michael P. Chemical Science, Vol. 6, Issue 2, p. 885-893 https://doi.org/10.1039/C4SC03030C	journal	January 2015
Molecular engineering of organic electroactive materials for redox flow batteries Ding, Yu; Zhang, Changkun; Zhang, Leyuan Chemical Society Reviews, Vol. 47, Issue 1 https://doi.org/10.1039/C7CS00569E	journal	January 2018
Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones Gerken, James B.; Stamoulis, Alexios; Suh, Sung-Eun Chemical Communications, Vol. 56, Issue 8 https://doi.org/10.1039/C9CC08878D	journal	January 2020
Mapping the frontiers of quinone stability in aqueous media: implications for organic aqueous redox flow batteries Tabor, Daniel P.; Gómez-Bombarelli, Rafael; Tong, Liuchuan Journal of Materials Chemistry A, Vol. 7, Issue 20 https://doi.org/10.1039/C9TA03219C	journal	January 2019
The Chemistry of Esters of Leuco Vat Dyes VI-The Supposed Production of Semiquinone Esters Dawson, A. M.; Johnson, A. Journal of the Society of Dyers and Colourists, Vol. 82, Issue 2 https://doi.org/10.1111/j.1478-4408.1966.tb02697.x	journal	February 1966
High Power Density Redox Flow Battery Cells Perry, M. L.; Darling, R. M.; Zaffou, R. ECS Transactions, Vol. 53, Issue 7 https://doi.org/10.1149/05307.0007ecst	journal	May 2013
Novel Quinone-Based Couples for Flow Batteries Huskinson, B.; Nawar, S.; Gerhardt, M. R. ECS Transactions, Vol. 53, Issue 7, p. 101-105 https://doi.org/10.1149/05307.0101ecst	journal	May 2013
Understanding and Mitigating Capacity Fade in Aqueous Organic Redox Flow Batteries Murali, Advaith; Nirmalchandar, Archith; Krishnamoorthy, Sankarganesh Journal of The Electrochemical Society, Vol. 165, Issue 7 https://doi.org/10.1149/2.0161807jes	journal	January 2018
A New Michael-Reaction-Resistant Benzoquinone for Aqueous Organic Redox Flow Batteries Hoober-Burkhardt, Lena; Krishnamoorthy, Sankarganesh; Yang, Bo Journal of The Electrochemical Society, Vol. 164, Issue 4 https://doi.org/10.1149/2.0351704jes	journal	January 2017
Flow Battery Molecular Reactant Stability Determined by Symmetric Cell Cycling Methods Goulet, Marc-Antoni; Aziz, Michael J. Journal of The Electrochemical Society, Vol. 165, Issue 7 https://doi.org/10.1149/2.0891807jes	journal	January 2018
An Inexpensive Aqueous Flow Battery for Large-Scale Electrical Energy Storage Based on Water-Soluble Organic Redox Couples Yang, Bo; Hoober-Burkhardt, Lena; Wang, Fang Journal of The Electrochemical Society, Vol. 161, Issue 9 https://doi.org/10.1149/2.1001409jes	journal	January 2014
The Critical Role of Supporting Electrolyte Selection on Flow Battery Cost Milshtein, Jarrod D.; Darling, Robert M.; Drake, Javit Journal of The Electrochemical Society, Vol. 164, Issue 14 https://doi.org/10.1149/2.1031714jes	journal	January 2017
High-Performance Aqueous Organic Flow Battery with Quinone-Based Redox Couples at Both Electrodes Yang, Bo; Hoober-Burkhardt, Lena; Krishnamoorthy, Sankarganesh Journal of The Electrochemical Society, Vol. 163, Issue 7 https://doi.org/10.1149/2.1371607jes	journal	January 2016
High-Performance Vanadium Redox Flow Batteries with Graphite Felt Electrodes Davies, Trevor; Tummino, Joseph C, Vol. 4, Issue 1 https://doi.org/10.3390/c4010008	journal	January 2018

Similar Records

Comparison of Quinone-Based Catholytes for Aqueous Redox Flow Batteries and Demonstration of Long-Term Stability with Tetrasubstituted Quinones

Journal Article · Tue May 26 00:00:00 EDT 2020 · Advanced Energy Materials · OSTI ID:1706729

Stable Tetrasubstituted Quinone Redox Reservoir for Enhancing Decoupled Hydrogen and Oxygen Evolution

Journal Article · Fri Mar 26 00:00:00 EDT 2021 · ACS Energy Letters · OSTI ID:1843014

Anthraquinone Derivatives in Aqueous Flow Batteries

Journal Article · Tue Dec 13 23:00:00 EST 2016 · Advanced Energy Materials · OSTI ID:1533067

Comparison of Quinone‐Based Catholytes for Aqueous Redox Flow Batteries and Demonstration of Long‐Term Stability with Tetrasubstituted Quinones

Citation Formats

References (36)

Similar Records

Related Subjects