An organic bifunctional redox active material for symmetric aqueous redox flow battery

Nambafu, Gabriel Sikukuu; Siddharth, Kumar; Zhang, Cheng; Zhao, Tianshou; Chen, Qing; Amine, Khalil; Shao, Minhua

doi:10.1016/j.nanoen.2021.106422

An organic bifunctional redox active material for symmetric aqueous redox flow battery

Journal Article · Wed Aug 11 00:00:00 EDT 2021 · Nano Energy

DOI:https://doi.org/10.1016/j.nanoen.2021.106422· OSTI ID:1866607

Nambafu, Gabriel Sikukuu ^[1]; Siddharth, Kumar ^[1]; Zhang, Cheng ^[1]; Zhao, Tianshou ^[1]; Chen, Qing ^[1]; Amine, Khalil ^[2]; Shao, Minhua ^[1]

Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon (Hong Kong)
Argonne National Lab. (ANL), Argonne, IL (United States); Stanford Univ., CA (United States); Imam AbduIrahman Bin Faisal Univ. (IAU), Dammam (Saudi Arabia)

Symmetric redox flow batteries utilizing a single redox active material as catholyte and anolyte, offer a plausible and unique strategy to alleviate cross-contamination issues during cycling, making them an ideal energy storage device for large scale applications. In this work, a low-cost riboflavin organic molecule is coupled with a 2,2,6,6-Tetramethylpiperidinyl-N-oxyl (TEMPO) radical molecule to form a single Riboflavin-TEMPO (RIBOTEMPO) bifunctional redox active material, which is used in both aqueous anolyte and catholyte. Cyclic voltammetry analysis of the combined molecule displays electrochemically reversible reactions for the redox couples at 0.72 V and 0.51 V versus Hg/Hg2SO4, leading to a theoretical cell voltage of 1.23 V. A symmetric cell testing demonstrated over 100 consecutive charge/discharge cycles with nearly 80% coulombic efficiency and capacity retention of 44.7% at a current density of 2.5 mA cm(-2). By utilizing a pH neutral supporting electrolyte, a lowcost, safe, and environmental-friendly redox flow battery is achieved. This work provides a pathway for the design and development of bifunctional redox active molecules for symmetric battery applications.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Vehicle Technologies Office; U.S.-China Clean Energy Research Center (CERC); Research Grants Council of the Hong Kong Special Administrative Region

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1866607

Alternate ID(s):: OSTI ID: 1869005

Journal Information:: Nano Energy, Journal Name: Nano Energy Journal Issue: Part: B Vol. 89; ISSN 2211-2855

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (52)

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
Flow Batteries: Alkaline Benzoquinone Aqueous Flow Battery for Large-Scale Storage of Electrical Energy (Adv. Energy Mater. 8/2018) Yang, Zhengjin; Tong, Liuchuan; Tabor, Daniel P. Advanced Energy Materials, Vol. 8, Issue 8 https://doi.org/10.1002/aenm.201870034	journal	March 2018
Porphyrin-Based Symmetric Redox-Flow Batteries towards Cold-Climate Energy Storage Ma, Ting; Pan, Zeng; Miao, Licheng Angewandte Chemie, Vol. 130, Issue 12 https://doi.org/10.1002/ange.201713423	journal	February 2018
A pH‐Neutral, Aqueous Redox Flow Battery with a 3600‐Cycle Lifetime: Micellization‐Enabled High Stability and Crossover Suppression Chai, Jingchao; Wang, Xiao; Lashgari, Amir ChemSusChem, Vol. 13, Issue 16 https://doi.org/10.1002/cssc.202001286	journal	July 2020
The structure of covalent hydrates of alloxazines. A reinvestigation Koziol, Jacek; Tyrakowska, Bozena; Müller, Franz Helvetica Chimica Acta, Vol. 64, Issue 6 https://doi.org/10.1002/hlca.19810640612	journal	September 1981
Novel 1-Aminomethylisatins: Peculiarities of the Synthesis and the Reaction with Tris(diethylamino)phosphine: Mannich Aminomethylation of Isatin Bogdanov, Andrei V.; Musin, Lenar I.; Il'in, Anton V. Journal of Heterocyclic Chemistry, Vol. 51, Issue 4 https://doi.org/10.1002/jhet.2011	journal	December 2013
Solubility Enhancement of Some Water-Insoluble Drugs in the Presence of Nicotinamide and Related Compounds Rasool, Alaa Abdul; Hussain, Anwar A.; Dittert, Lewis W. Journal of Pharmaceutical Sciences, Vol. 80, Issue 4 https://doi.org/10.1002/jps.2600800422	journal	April 1991
An Approach Toward Replacing Vanadium: A Single Organic Molecule for the Anode and Cathode of an Aqueous Redox-Flow Battery Janoschka, Tobias; Friebe, Christian; Hager, Martin D. ChemistryOpen, Vol. 6, Issue 2 https://doi.org/10.1002/open.201600155	journal	February 2017
Riboflavin degradation in the presence of quercetin in methanol under continuous UV-B irradiation: the ESI–MS–UHPLC analysis Stanojević, Jelena S.; Zvezdanović, Jelena B.; Marković, Dejan Z. Monatshefte für Chemie - Chemical Monthly, Vol. 146, Issue 11 https://doi.org/10.1007/s00706-015-1561-1	journal	September 2015
Aqueous organic redox flow batteries Singh, Vikram; Kim, Soeun; Kang, Jungtaek Nano Research, Vol. 12, Issue 9 https://doi.org/10.1007/s12274-019-2355-2	journal	March 2019
Effect of a mixture of caffeine and nicotinamide on the solubility of vitamin (B2) in aqueous solution Evstigneev, M. P.; Evstigneev, V. P.; Santiago, A. A. Hernandez European Journal of Pharmaceutical Sciences, Vol. 28, Issue 1-2 https://doi.org/10.1016/j.ejps.2005.12.010	journal	May 2006
A bipolar verdazyl radical for a symmetric all-organic redox flow-type battery Charlton, Grant D.; Barbon, Stephanie M.; Gilroy, Joe B. Journal of Energy Chemistry, Vol. 34 https://doi.org/10.1016/j.jechem.2018.09.020	journal	July 2019
The impact of pH on side reactions for aqueous redox flow batteries based on nitroxyl radical compounds Orita, A.; Verde, M. G.; Sakai, M. Journal of Power Sources, Vol. 321 https://doi.org/10.1016/j.jpowsour.2016.04.136	journal	July 2016
Redox flow batteries: Status and perspective towards sustainable stationary energy storage Sánchez-Díez, Eduardo; Ventosa, Edgar; Guarnieri, Massimo Journal of Power Sources, Vol. 481 https://doi.org/10.1016/j.jpowsour.2020.228804	journal	January 2021
A review of energy storage technologies for wind power applications Díaz-González, Francisco; Sumper, Andreas; Gomis-Bellmunt, Oriol Renewable and Sustainable Energy Reviews, Vol. 16, Issue 4 https://doi.org/10.1016/j.rser.2012.01.029	journal	May 2012
Climate change impacts on renewable energy generation. A review of quantitative projections Solaun, Kepa; Cerdá, Emilio Renewable and Sustainable Energy Reviews, Vol. 116 https://doi.org/10.1016/j.rser.2019.109415	journal	December 2019
Mannich Reaction of Indole with Cyclic Imines in Water Xie, Liang-Hui; Cheng, Jie; Luo, Zi-Wei Tetrahedron Letters, Vol. 59, Issue 5 https://doi.org/10.1016/j.tetlet.2017.12.069	journal	January 2018
Electrolyte Lifetime in Aqueous Organic Redox Flow Batteries: A Critical Review Kwabi, David G.; Ji, Yunlong; Aziz, Michael J. Chemical Reviews, Vol. 120, Issue 14 https://doi.org/10.1021/acs.chemrev.9b00599	journal	February 2020
A Practical Beginner’s Guide to Cyclic Voltammetry Elgrishi, Noémie; Rountree, Kelley J.; McCarthy, Brian D. Journal of Chemical Education, Vol. 95, Issue 2 https://doi.org/10.1021/acs.jchemed.7b00361	journal	November 2017
Structural Effects on the pH-Dependent Redox Properties of Organic Nitroxyls: Pourbaix Diagrams for TEMPO, ABNO, and Three TEMPO Analogs Gerken, James B.; Pang, Yutong Q.; Lauber, Markus B. The Journal of Organic Chemistry, Vol. 83, Issue 14 https://doi.org/10.1021/acs.joc.7b02547	journal	November 2017
Effects of Shapes of Solute Molecules on Diffusion: A Study of Dependences on Solute Size, Solvent, and Temperature Chan, T. C.; Li, H. T.; Li, K. Y. The Journal of Physical Chemistry B, Vol. 119, Issue 51 https://doi.org/10.1021/acs.jpcb.5b10550	journal	December 2015
Abundant Organic Dye as an Anolyte for Aqueous Flow Battery with Multielectron Transfer Mukhopadhyay, Alolika; Zhao, Huijuan; Li, Bin ACS Applied Energy Materials, Vol. 2, Issue 10 https://doi.org/10.1021/acsaem.9b01429	journal	September 2019
Stable Low-Cost Organic Dye Anolyte for Aqueous Organic Redox Flow Battery Lai, Yun Yu; Li, Xiang; Liu, Kewei ACS Applied Energy Materials, Vol. 3, Issue 3 https://doi.org/10.1021/acsaem.9b01735	journal	February 2020
On Lifetime and Cost of Redox-Active Organics for Aqueous Flow Batteries Brushett, Fikile R.; Aziz, Michael J.; Rodby, Kara E. ACS Energy Letters, Vol. 5, Issue 3 https://doi.org/10.1021/acsenergylett.0c00140	journal	February 2020
TEMPO/Phenazine Combi-Molecule: A Redox-Active Material for Symmetric Aqueous Redox-Flow Batteries Winsberg, Jan; Stolze, Christian; Muench, Simon ACS Energy Letters, Vol. 1, Issue 5 https://doi.org/10.1021/acsenergylett.6b00413	journal	October 2016
Multielectron Cycling of a Low-Potential Anolyte in Alkali Metal Electrolytes for Nonaqueous Redox Flow Batteries Hendriks, Koen H.; Sevov, Christo S.; Cook, Monique E. ACS Energy Letters, Vol. 2, Issue 10 https://doi.org/10.1021/acsenergylett.7b00559	journal	September 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
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
Molecular Engineering Strategies for Symmetric Aqueous Organic Redox Flow Batteries Fornari, Rocco Peter; Mesta, Murat; Hjelm, Johan ACS Materials Letters, Vol. 2, Issue 3 https://doi.org/10.1021/acsmaterialslett.0c00028	journal	February 2020
Carboxyl-Functionalized TEMPO Catholyte Enabling High-Cycling-Stability and High-Energy-Density Aqueous Organic Redox Flow Batteries Liu, Bin; Tang, Chun Wai; Jiang, Haoran ACS Sustainable Chemistry & Engineering, Vol. 9, Issue 18 https://doi.org/10.1021/acssuschemeng.0c08946	journal	April 2021
Highly Soluble 1,4-Diaminoanthraquinone Derivative for Nonaqueous Symmetric Redox Flow Batteries Geysens, Pieter; Li, Yun; Vankelecom, Ivo ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 9 https://doi.org/10.1021/acssuschemeng.9b07244	journal	February 2020
Mechanisms of isoalloxazine (flavine) hydrolysis Smith, Stephen B.; Bruice, Thomas C. Journal of the American Chemical Society, Vol. 97, Issue 10 https://doi.org/10.1021/ja00843a043	journal	May 1975
Alkaline Hydrolysis of Riboflavin Surrey, Alexander R.; Nachod, Frederick C. Journal of the American Chemical Society, Vol. 73, Issue 5 https://doi.org/10.1021/ja01149a128	journal	May 1951
The Effect of Nicotinamide on the Solubility of Riboflavin in Water Frost, Douglas V. Journal of the American Chemical Society, Vol. 69, Issue 5 https://doi.org/10.1021/ja01197a027	journal	May 1947
Effect of Nicotinamide and Urea on the Solubility of Riboflavin in Various Solvents Coffman, Renée E.; Kildsig, Dane O. Journal of Pharmaceutical Sciences, Vol. 85, Issue 9 https://doi.org/10.1021/js960012b	journal	September 1996
Highly Efficient One-Pot Three-Component Mannich Reaction in Water Catalyzed by Heteropoly Acids Azizi, Najmodin; Torkiyan, Lalleh; Saidi, Mohammad R. Organic Letters, Vol. 8, Issue 10 https://doi.org/10.1021/ol060498v	journal	April 2006
A bipolar nitronyl nitroxide small molecule for an all-organic symmetric redox-flow battery Hagemann, Tino; Winsberg, Jan; Häupler, Bernhard NPG Asia Materials, Vol. 9, Issue 1 https://doi.org/10.1038/am.2016.195	journal	January 2017
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 biomimetic redox flow battery based on flavin mononucleotide Orita, Akihiro; Verde, Michael G.; Sakai, Masanori Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13230	journal	October 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
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
Thermal decay of TEMPO in acidic media via an N-oxoammonium salt intermediate Ma, Yun; Loyns, Colin; Price, Peter Organic & Biomolecular Chemistry, Vol. 9, Issue 15 https://doi.org/10.1039/c1ob05475a	journal	January 2011
Progress in redox flow batteries, remaining challenges and their applications in energy storage Leung, Puiki; Li, Xiaohong; Ponce de León, Carlos RSC Advances, Vol. 2, Issue 27 https://doi.org/10.1039/c2ra21342g	journal	January 2012
Hydrolysis products of flavins (isoalloxazines) Harayama, Takashi; Tezuka, Yasuhiro; Taga, Tooru Journal of the Chemical Society, Perkin Transactions 1 https://doi.org/10.1039/p19870000075	journal	January 1987
Finite-size effects of diffusion coefficients computed from molecular dynamics: a review of what we have learned so far Celebi, Alper T.; Jamali, Seyed Hossein; Bardow, André Molecular Simulation, Vol. 47, Issue 10-11 https://doi.org/10.1080/08927022.2020.1810685	journal	September 2020
Vanadium Redox Flow Batteries: Potentials and Challenges of an Emerging Storage Technology Guarnieri, Massimo; Mattavelli, Paolo; Petrone, Giovanni IEEE Industrial Electronics Magazine, Vol. 10, Issue 4 https://doi.org/10.1109/MIE.2016.2611760	journal	January 2016
Battery Technologies for Large-Scale Stationary Energy Storage Soloveichik, Grigorii L. Annual Review of Chemical and Biomolecular Engineering, Vol. 2, Issue 1, p. 503-527 https://doi.org/10.1146/annurev-chembioeng-061010-114116	journal	July 2011
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
Advanced Redox-Flow Batteries: A Perspective Perry, Mike L.; Weber, Adam Z. Journal of The Electrochemical Society, Vol. 163, Issue 1 https://doi.org/10.1149/2.0101601jes	journal	September 2015
On the Benefits of a Symmetric Redox Flow Battery Potash, Rebecca A.; McKone, James R.; Conte, Sean Journal of The Electrochemical Society, Vol. 163, Issue 3 https://doi.org/10.1149/2.0971602jes	journal	December 2015

Similar Records

A Stable, Low Permeable TEMPO Catholyte for Aqueous Total Organic Redox Flow Batteries

Journal Article · Fri Dec 17 23:00:00 EST 2021 · Advanced Energy Materials · OSTI ID:1968560

Related Subjects

25 ENERGY STORAGE
36 MATERIALS SCIENCE
Bipolar organic molecules
Redox active materials
Symmetric aqueous redox flow battery

An organic bifunctional redox active material for symmetric aqueous redox flow battery

Citation Formats

References (52)

Similar Records

Related Subjects