Quinones having high capacity retention for use as electrolytes in aqueous redox flow batteries

Aziz, Michael J.; Gordon, Roy G.; Lin, Kaixiang; Kwabi, David Gator; Ji, Yunlong

Title: Quinones having high capacity retention for use as electrolytes in aqueous redox flow batteries

Patent · Tue Aug 15 00:00:00 EDT 2023

OSTI ID:2222104

Aziz, Michael J.; Gordon, Roy G.; Lin, Kaixiang; Kwabi, David Gator; Ji, Yunlong

We disclose quinone compounds and related species (Formula I) that possess significant advantages when used as a redox active material in a battery, e.g., a redox flow battery. In particular, the compounds provide redox flow batteries (RFBs) with extremely high capacity retention. For example, RFBs of the invention can be cycled for 500 times with negligible loss of capacity, and such batteries could be employed for years of service. Thus, the invention provides a high efficiency, long cycle life redox flow battery with reasonable power cost, low energy cost, and all the energy scaling advantages of a flow battery.

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Research Organization:: STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH This invention was made with government support under DE-AC05-76RL01830, DE-AR0000348, and DE-AR0000767 awarded by the U.S. Department of Energy and under 1509041 awarded by the National Science Foundation. The government has certain rights to the invention.

Sponsoring Organization:: USDOE; National Science Foundation (NSF)

DOE Contract Number:: AC05-76RL01830; AR0000348; AR0000767; 1509041

Assignee:: President and Fellows of Harvard College (Cambridge, MA)

Patent Number(s):: 11,724,980

Application Number:: 16/968,684

OSTI ID:: 2222104

Resource Relation:: Patent File Date: 02/11/2019

Country of Publication:: United States

Language:: English

References (105)

CO₂ Reduction at Low Overpotential on Cu Electrodes Resulting from the Reduction of Thick Cu₂O Films Li, Christina W.; Kanan, Matthew W. Journal of the American Chemical Society, Vol. 134, Issue 17, p. 7231-7234 https://doi.org/10.1021/ja3010978	journal	April 2012
Recording medium and information recording and reproducing method using the same Inagaki, Yoshio; Naya, Masayuki https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060194151 US Patent Application 11/327521; 20060194151	patent-application	August 2006
Electrochemical Approach to the Mechanistic Study of Proton-Coupled Electron Transfer Costentin, Cyrille Chemical Reviews, Vol. 108, Issue 7 https://doi.org/10.1021/cr068065t	journal	July 2008
Reduction Potentials Of Quinones. II. The Potentials Of Certain Derivatives Of Benzoquinone, Naphthoquinone And Anthraquinone Conant, James B.; Fieser, Louis F. Journal of the American Chemical Society, Vol. 46, Issue 8, p. 1858-1881 https://doi.org/10.1021/ja01673a014	journal	August 1924
Flow battery with electrolyte rebalancing system Chen, Qing; Gordon, Roy G.; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/10840532 US Patent Document 10,840,532	patent	November 2020
Method for Manufacturing Secondary Battery and Method for Preparing Positive Electrode Active Material for Secondary Battery Ohtsuka, Yu; Hojo, Nobuhiko https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090094822 US Patent Application 12/295992; 20090094822	patent-application	April 2009
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
Reduction potentials for 2,2'-bipyridine and 1,10-phenanthroline couples in aqueous solutions Krishnan, C. V.; Creutz, Carol; Schwarz, Harold A. Journal of the American Chemical Society, Vol. 105, Issue 17 https://doi.org/10.1021/ja00355a015	journal	August 1983
Electrochromic Compounds with Improved Color Stability in Their Radical States Lin, Rongguang; Baumann, Kelvin L.; Giri, Punam https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20160229803 US Patent Application 15/040946; 20160229803	patent-application	August 2016
Simple preparative synthesis of spinochrome e, a pigment from sea urchins of the genus Echinothrix Borisova, K. L.; Anufriev, V. F. Chemistry of Natural Compounds, Vol. 48, Issue 2, p. 202-204 https://doi.org/10.1007/s10600-012-0204-6	journal	May 2012
Fuel cells Knuckey, Kathryn; Creeth, Andrew Martin https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8492048 US Patent Document 8,492,048	patent	July 2013
Flow-through electrolytic cell Noding, Stephen A. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/4652355 US Patent Document 4,652,355	patent	March 1987
Alkaline Quinone Flow Battery with Long Lifetime at pH 12 Kwabi, David G.; Lin, Kaixiang; Ji, Yunlong Joule, Vol. 2, Issue 9 https://doi.org/10.1016/j.joule.2018.07.005	journal	September 2018
Information recording medium Wariishi, Koji https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6020105 US Patent Document 6,020,105	patent	February 2000
Coordination Compounds Having Redox Non-Innocent Ligands and Flow Batteries Containing the Same Millard, Matthew https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20170291916 US Patent Application 15/093606; 20170291916	patent-application	October 2017
Anthraquinone Flow Battery Reactants with Nonhydrolyzable Water-Solubilizing Chains Introduced via a Generic Cross-Coupling Method Jing, Yan; Fell, Eric M.; Wu, Min ACS Energy Letters, Vol. 7, Issue 1 https://doi.org/10.1021/acsenergylett.1c02504	journal	December 2021
Method and Apparatus of Generating Electric Power Shimomura, Tatsuo; Komatsu, Makoto; Adachi, Masanori https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070134520 US Patent Application 11/556883; 20070134520	patent-application	June 2007
Analytical applications of 1,10-anthraquinones: A review Diaz, Aurora Navas Talanta, Vol. 38, Issue 6, p. 571-588 https://doi.org/10.1016/0039-9140(91)80140-U	journal	June 1991
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
Small Organic Molecule Based Flow Battery Huskinson, Brian; Marshak, Michael; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20160043423 US Patent Application 14/823546; 20160043423	patent-application	February 2016
Voltammetry of Quinones in Unbuffered Aqueous Solution: Reassessing the Roles of Proton Transfer and Hydrogen Bonding in the Aqueous Electrochemistry of Quinones Quan, May; Sanchez, Daniel; Wasylkiw, Mark F. Journal of the American Chemical Society, Vol. 129, Issue 42, p. 12847-12856 https://doi.org/10.1021/ja0743083	journal	October 2007
Novel organic redox flow batteries using soluble quinonoid compounds as positive materials Xu, Yan; Wen, Yuehua; Cheng, Jie 2009 World Non-Grid-Connected Wind Power and Energy Conference https://doi.org/10.1109/WNWEC.2009.5335870	conference	September 2009
Redox Flow Cell Comprising High Molecular Weight Compounds as Redox Pair and Semipermeable Membrane for Storage of Electrical Energy Schubert, Ulrich Signar; Hager, Martin; Janoschka, Tobias https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20150207165 US Patent Application 14/420,675; 2015/0207165 Al	patent-application	July 2015
Method of photochemical immobilization of ligands using quinones Jacobsen, Morten; Koch, Troels https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6033784 US Patent Document 6,033,784	patent	March 2000
Systems and methods for series battery charging Taylor, Tony L.; Ota, Naoki; Tan, Taison https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/10153651 US Patent Document 10,153,651	patent	December 2018
Self-assembled surfactant structures Brozell, Adrian https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/10589231 US Patent Document 10,589,231	patent	March 2020
1,1′,8,8′-Tetramethoxy-10,10′-bianthrone Shi, Zheng-Wei; Li, Yi-Zhi; Li, Ying Acta Crystallographica Section E Structure Reports Online, Vol. 60, Issue 12 https://doi.org/10.1107/S1600536804028168	journal	November 2004
Inexpensive metal-free organic redox flow battery (ORBAT) for grid-scale storage Narayan, Sri R.; Prakash, Surya; Yang, Bo https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/9614245 US Patent Document 9,614,245	patent	April 2017
Rebalancing Electrolytes in Redox Flow Battery Systems Chang, On Kok; Pham, Ai Quoc https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20150104724 US Patent Application 14/577368; 20150104724	patent-application	April 2015
A study of tiron in aqueous solutions for redox flow battery application Xu, Yan; Wen, Yue-Hua; Cheng, Jie Electrochimica Acta, Vol. 55, Issue 3, p. 715-720 https://doi.org/10.1016/j.electacta.2009.09.031	journal	January 2010
Fluid-surfaced electrode Deane, Geoffrey F.; Ferren, Bran; Gates, William https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20110027624 US Patent Application 12/462205; 20110027624	patent-application	February 2011
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
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
Electrical Energy Storage Apparatus Rightmire, Robert A. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/3288641 US Patent Document 3,288,641	patent	November 1966
134. Ferrocene derivatives. Part VII. Some sulphur derivatives Knox, G. R.; Pauson, P. L. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9580000692	journal	January 1958
Reduction Potentials Of Quinones. I. The Effect Of The Solvent On The Potentials Of Certain Benzoquinones Conant, James B.; Fieser, Louis F. Journal of the American Chemical Society, Vol. 45, Issue 9, p. 2194-2218 https://doi.org/10.1021/ja01662a027	journal	September 1923
Quinone and hydroquinone based flow battery Huskinson, Brian; Marshak, Michael; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/10847829 US Patent Document 10,847,829	patent	November 2020
Oxidoreductase reaction control and use thereof Amao, Yutaka; Ikeyama, Shusaku; Nakanishi, Yuji https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/9777299 US Patent Document 9,777,299	patent	October 2017
The pH-Rate Profile for the Hydrolysis of a Peptide Bond Smith, Robert M.; Hansen, David E. Journal of the American Chemical Society, Vol. 120, Issue 35 https://doi.org/10.1021/ja9804565	journal	September 1998
Systems and Methods for Series Battery Charging Taylor, Tony L.; Ota, Naoki; Tan, Taison https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20160105042 US Patent Document 14/879599; 20160105042	patent-application	April 2016
Extremely Stable Anthraquinone Negolytes Synthesized from Common Precursors Wu, Min; Jing, Yan; Wong, Andrew A. Chem, Vol. 6, Issue 6 https://doi.org/10.1016/j.chempr.2020.03.021	journal	June 2020
Method of Generating Electricity Using a Polyhydric Phenol-Oxygen Fuel Cell Klass, Donald L.; Hutchings, Le Roi E. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/3238066 US Patent Document 3,238,066	patent	March 1966
Alkaline quinone flow battery Lin, K.; Chen, Q.; Gerhardt, M. R. Science, Vol. 349, Issue 6255, p. 1529-1532 https://doi.org/10.1126/science.aab3033	journal	September 2015
Redox Flow Battery and Method of Operating the Same Dong, Yongrong; Shigematsu, Toshio; Kumamoto, Takahiro https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20130157162 US Patent Application 13/638323; 20130157162	patent-application	June 2013
Redox Flow Battery System for Distributed Energy Storage Horne, Craig R.; Kinoshita, Kim; Hickey, Darren B. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20110045332 US Patent Document 12/883511; 20110045332	patent-application	February 2011
Benzoquinone-Hydroquinone Couple for Flow Battery Nawar, Saraf; Huskinson, Brian; Aziz, Michael MRS Proceedings, Vol. 1491 https://doi.org/10.1557/opl.2012.1737	journal	January 2013
Fuel cell using quinones to oxidize hydroxylic compounds Hertl, William; Schaeffler, Robert https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/4578323 US Patent Document 4,578,323	patent	March 1986
Small organic molecule based flow battery Huskinson, Brian; Marshak, Michael; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/9966622 US Patent Document 9,966,622	patent	May 2018
Cycling of a Quinone-Bromide Flow Battery for Large-Scale Electrochemical Energy Storage Huskinson, B.; Marshak, M. P.; Gerhardt, M. R. ECS Transactions, Vol. 61, Issue 37, p. 27-30 https://doi.org/10.1149/06137.0027ecst	journal	September 2014
Metal complexes of substituted catecholates and redox flow batteries containing the same Reece, Steven Y. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/9837679 US Patent Document 9,837,679	patent	December 2017
Anthraquinone with tailored structure for a nonaqueous metal–organic redox flow battery Wang, Wei; Xu, Wu; Cosimbescu, Lelia Chemical Communications, Vol. 48, Issue 53, p. 6669-6671 https://doi.org/10.1039/c2cc32466k	journal	January 2012
Cooking method for pulp Audoh, Tatsuya; Tanaka, Junji; Watanabe, Keigo https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20020088576 US Patent Application 10/015704; 20020088576	patent-application	July 2002
High pH Organic Flow Battery Aziz, Michael J.; Gordon, Ray G.; Lin, Kaixiang https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20180048011 US Patent Application 15/556140; 20180048011	patent-application	February 2018
Anticancer Effect and Structure-Activity Analysis of Marine Products Isolated from Metabolites of Mangrove Fungi in the South China Sea Tao, Li-yang; Zhang, Jian-ye; Liang, Yong-ju Marine Drugs, Vol. 8, Issue 4 https://doi.org/10.3390/md8041094	journal	April 2010
High Energy Density Aqueous Flow Battery Utilizing Extremely Stable, Branching-Induced High-Solubility Anthraquinone near Neutral pH Kerr, Emily F.; Tang, Zhijiang; George, Thomas Y. ACS Energy Letters, Vol. 8, Issue 1 https://doi.org/10.1021/acsenergylett.2c01691	journal	December 2022
Charge Transfer Mediator Based Systems for Electrocatalytic Oxygen Reduction Stahl, Shannon S.; Gerken, James B.; Anson, Colin W. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20170279148 US Patent Application 15/617181; 20170279148	patent-application	September 2017
High-capacity organic positive-electrode material based on a benzoquinone derivative for use in rechargeable lithium batteries Yao, Masaru; Senoh, Hiroshi; Yamazaki, Shin-ichi Journal of Power Sources, Vol. 195, Issue 24, p. 8336-8340 https://doi.org/10.1016/j.jpowsour.2010.06.069	journal	December 2010
Methods for use of a photobiofuel cell in production of hydrogen and other materials Gust, JR., John Devens; Moore, Ana L.; Moore, Thomas A. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070184309 US Patent Application 10/558598; 20070184309	patent-application	August 2007
Flow Battery with Electrolyte Rebalancing System Chen, Qing; Gordon, Roy G.; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20180219241 US Patent Application 15/882032; 20180219241	patent-application	August 2018
Electrochemical CO₂ Reduction on Metal Electrodes Hori, Y.; Vayenas, Constantinos G.; White, Ralph E. Modern Aspects of Electrochemistry, p. 89-189 https://doi.org/10.1007/978-0-387-49489-0_3	book	January 2008
Self-Assembled Surfactant Structures Brozell, Adrian https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20110284456 US Patent Application 13/113930; 20110284456	patent-application	November 2011
Electrochromic compounds with improved color stability in their radical states Lin, Rongguang; Baumann, Kelvin L.; Giri, Punam https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/10040763 US Patent Document 10,040,763	patent	August 2018
Charge transfer mediator based systems for electrocatalytic oxygen reduction Stahl, Shannon S.; Gerken, James B.; Anson, Colin W. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/9812727 US Patent Document 9,812,727	patent	November 2017
Substituted anthraquinones and use thereof in epoxy resins Howell, Frederick H.; Duthaler, Rudolf; Finter, Jurgen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/4924015 US Patent Document 4,924,015	patent	May 1990
Quinone and Hydroquinone Based Flow Battery Huskinson, Brian; Marshak, Michael; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20160248114 US Patent Application 15/025040; 20160248114	patent-application	August 2016
Cascade Redox Flow Battery Systems Horne, Craig R.; Kinoshita, Kim; HIckey, Darren B. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20110223450 US Patent Application 12/986892; 20110223450	patent-application	September 2011
Fuel Cells Knuckey, Kathryn; Creeth, Andrew https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20100112393 US Patent Application 12/374352; 20100112393	patent-application	May 2010
Aqueous Redox Flow Battery Electrolytes with High Chemical and Electrochemical Stability, High Water Solubility, Low Membrane Permeability Gordon, Roy G.; Aziz, Michael J.; Beh, Eugene https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20200373599 US Patent Application 16/324951; 20200373599	patent-application	November 2020
Oxidoreductase Reaction Control and Use Thereof Amao, Yutaka; Ikeyama, Shusaku; Nakanishi, Yuji https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20150176037 US Patent Application 14/408127; 20150176037	patent-application	June 2015
A high power density, high efficiency hydrogen–chlorine regenerative fuel cell with a low precious metal content catalyst Huskinson, Brian; Rugolo, Jason; Mondal, Sujit K. Energy & Environmental Science, Vol. 5, Issue 9 https://doi.org/10.1039/c2ee22274d	journal	January 2012
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
Redox flow battery system for distributed energy storage Horne, Craig R.; Kinoshita, Kim; Hickey, Darren https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8906529 US Patent Document 8,906,529	patent	December 2014
Operating A Redox Flow Battery With A Negative Electrolyte Imbalance Pham, Quoc; Chang, On; Durairaj, Sumitha https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20140186731 US Patent Application 14/095362; 20140186731	patent-application	July 2014
Small Organic Molecule Based Flow Battery Huskinson, Brian; Marshak, Michael; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20150243991 US Patent Application 14/431175; 20150243991	patent-application	August 2015
Fuel Cell Device with Electrolytes Flowing by Means of Percolation Through Electrodes Having A Porous, Three-Dimensional Structure Lavastre, Olivier; Floner, Didier; Paris, Dominique https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20150079497 US Patent Application 14/391895; 20150079497	patent-application	March 2015
Evaluation of organic battery electrodes: Voltammetric study of the redox behaviour of solid quinones Alt, H.; Binder, H.; Klempert, G. Journal of Applied Electrochemistry, Vol. 2, Issue 3, p. 193-200 https://doi.org/10.1007/BF02354976	journal	August 1972
Differential pH as a method for increasing cell potential in organic aqueous flow batteries Khataee, Amirreza; Wedege, Kristina; Dražević, Emil J. Mater. Chem. A, Vol. 5, Issue 41 https://doi.org/10.1039/C7TA04975G	journal	January 2017
Electrochemistry of the viologens Bird, C. L.; Kuhn, A. T. Chemical Society Reviews, Vol. 10, Issue 1 https://doi.org/10.1039/cs9811000049	journal	January 1981
Redox flow battery and method of operating the same Dong, Yongrong; Shigematsu, Toshio; Kumamoto, Takahiro https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8632903 US Patent Document 8,632,903	patent	January 2014
The electrochemical reduction of anthraquinone to anthrone in concentrated H2SO4 Comninellis, Ch.; Plattner, E. Journal of Applied Electrochemistry, Vol. 15, Issue 5 https://doi.org/10.1007/BF00620574	journal	September 1985
Anthraquinone Derivatives in Aqueous Flow Batteries Gerhardt, Michael R.; Tong, Liuchuan; Gómez-Bombarelli, Rafael Advanced Energy Materials, Vol. 7, Issue 8 https://doi.org/10.1002/aenm.201601488	journal	December 2016
Method for manufacturing secondary battery and method for preparing positive electrode active material for secondary battery Ohtsuka, Yu; Hojo, Nobuhiko https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8263241 US Patent Document 8,263,241	patent	September 2012
Cascade redox flow battery systems Horne, Craig R.; Kinoshita, Kim; Hickey, Darren https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8785023 US Patent Document 8,785,023	patent	July 2014
Air-Breathing Aqueous Sulfur Rechargeable Batteries Su, Liang; Li, Zheng; Chiang, Yet-Ming https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20180241107 US Patent Application 15/957027; 20180241107	patent-application	August 2018
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
A Neutral pH Aqueous Organic–Organometallic Redox Flow Battery with Extremely High Capacity Retention Beh, Eugene S.; De Porcellinis, Diana; Gracia, Rebecca L. ACS Energy Letters, Vol. 2, Issue 3 https://doi.org/10.1021/acsenergylett.7b00019	journal	February 2017
Molecularly Tunable Heterogeneous Catalysts by Edge Functionalization of Graphitic Carbons Surendranath, Yogesh; Fukushima, Tomohiro; O'Reilly, Matthew E. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20170047592 US Patent Application 15/236963; 20170047592	patent-application	February 2017
Quinone and Hydroquinone Based Flow Battery Huskinson, Brian; Marshak, Michael; Aziz, Michael J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20210083311 US Patent Application 17/101571; 20210083311	patent-application	March 2021
Operating a redox flow battery with a negative electrolyte imbalance Pham, Quoc Thai; Chang, On-Kok; Durairaj, Sumitha https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8993183 US Patent Document 8,993,183	patent	March 2015
Methyl viologen reactions. 5. Rates and mechanism of cation-radical formation in aqueous base Rieger, Anne L.; Edwards, John O. The Journal of Organic Chemistry, Vol. 53, Issue 7 https://doi.org/10.1021/jo00242a025	journal	April 1988
Electrochromic materials Mortimer, Roger J. Chemical Society Reviews, Vol. 26, Issue 3 https://doi.org/10.1039/cs9972600147	journal	January 1997
Redox flow batteries a review Weber, Adam Z.; Mench, Matthew M.; Meyers, Jeremy P. Journal of Applied Electrochemistry, Vol. 41, Issue 10, p. 1137-1164 https://doi.org/10.1007/s10800-011-0348-2	journal	September 2011
Fluid-surfaced electrode Deane, Geoffrey F.; Ferren, Bran; Gates, William https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8460814 US Patent Document 8,460,814	patent	June 2013
Inexpensive Metal-Free Organic Redox Flow Battery (Orbat) for Grid-Scale Storage Narayan, Sri; Prakash, Surya G. K.; Yang, Bo https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20140370403 US Patent Application 14/307030; 20140370403	patent-application	December 2014
Cooking method for pulp Andoh, Tatsuya; Tanaka, Junji; Watanabe, Keigo https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7056418 US Patent Document 7,056,418	patent	June 2006
A Quinone-Bromide Flow Battery with 1 W/cm² Power Density Chen, Qing; Gerhardt, Michael R.; Hartle, Lauren Journal of The Electrochemical Society, Vol. 163, Issue 1, p. A5010-A5013 https://doi.org/10.1149/2.0021601jes	journal	July 2015
A Total Organic Aqueous Redox Flow Battery Employing a Low Cost and Sustainable Methyl Viologen Anolyte and 4-HO-TEMPO Catholyte Liu, Tianbiao; Wei, Xiaoliang; Nie, Zimin Advanced Energy Materials, Vol. 6, Issue 3, 1501449 https://doi.org/10.1002/aenm.201501449	journal	December 2015
Secondary Battery, Power Supply System Using Same and Usage of Power Supply System Inatomi, Yuu; Hojo, Nobuhiko; Kuranuki, Masaaki https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090017379 US Patent Application 11/915456; 20090017379	patent-application	January 2009
High Energy Density Redox Flow Device Carter, William; Chiang, Yet-Ming; Duduta, Mihai https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20110189520 US Patent Application 12/970773; 20110189520	patent-application	August 2011
Apparatus and Method for Electrochemically Generating Electricity with Polyhydric Phenol Polymer Klass, Donal L. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/3300342 US Patent Document 3,300,342	patent	January 1967
Reversible hydrogen storage using CO₂ and a proton-switchable iridium catalyst in aqueous media under mild temperatures and pressures Hull, Jonathan F.; Himeda, Yuichiro; Wang, Wan-Hui Nature Chemistry, Vol. 4, Issue 5, p. 383-388 https://doi.org/10.1038/nchem.1295	journal	March 2012
Free And Total Energy Changes In The Reduction Of Quinones Conant, James B.; Fieser, Louis F. Journal of the American Chemical Society, Vol. 44, Issue 11, p. 2480-2493 https://doi.org/10.1021/ja01432a016	journal	November 1922
Carbon monoxide-oxygen fuel cell Ishida, Tetsuyoshi; Okiura, Kunio; Hanayama, Fumihiko https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/4711828 US Patent Document 4,711,828	patent	December 1987
Electron Self-Exchange Kinetics for a Water-Soluble Ferrocenium/Ferrocene Couple: Rate Modulation via Charge Dependent Calix[6]arene- p -sulfonate Encapsulation Nielson, Roger M.; Hupp, Joseph T. Inorganic Chemistry, Vol. 35, Issue 5 https://doi.org/10.1021/ic951191n	journal	January 1996
High energy density redox flow device Chiang, Yet-Ming; Carter, William Craig; Duduta, Mihai https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8722226 US Patent Document 8,722,226	patent	May 2014

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