A biomimetic high-capacity phenazine-based anolyte for aqueous organic redox flow batteries

Hollas, Aaron; Wei, Xiaoliang; Murugesan, Vijayakumar; Nie, Zimin; Li, Bin; Reed, David; Liu, Jun; Sprenkle, Vincent; Wang, Wei

doi:10.1038/s41560-018-0167-3

A biomimetic high-capacity phenazine-based anolyte for aqueous organic redox flow batteries

Journal Article · Fri Jun 01 00:00:00 EDT 2018 · Nature Energy

DOI:https://doi.org/10.1038/s41560-018-0167-3· OSTI ID:1490220

Hollas, Aaron; Wei, Xiaoliang; Murugesan, Vijayakumar; Nie, Zimin; ; Reed, David; Liu, Jun; Sprenkle, Vincent; Wang, Wei

Redox flow batteries (RFB) for use as a stationary energy storage system require redox-active materials with high capacity, stability, and sustainability. Aqueous soluble organic (ASO) redox-active materials have recently attracted significant attention as alternatives to traditional transition metal ions. However, reported reversible capacities are substantially lower than their theoretical values based on solubility. In this paper, we describe a phenazine-based ASO compound with an exceptionally high reversible capacity that exceeds 90% of its theoretical solubility value. In our combined nuclear magnetic resonance (NMR) and density functional theory (DFT) study, we discovered that by strategically modifying the phenazine molecular structure, preferential solvation is enabled, thereby increasing the solubility of the phenazine from near-zero to as much as 1.8 M, while its redox potential can be shifted by more than 400 mV. An RFB based on the highly alkaline-soluble and two-electron transfer phenazine derivative, 7,8-dihydroxyphenazine-2-sulfonic acid exhibits an operating voltage at 1.4 V and capacity retention of 99.98% per cycle over 500 cycles at a reversible capability of 67 Ah L-1. Development of this phenazine compound represents a new approach for realizing energy-dense, cost-effective ASO flow batteries for stationary energy storage applications.

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1490220

Report Number(s):: PNNL-SA-130788

Journal Information:: Nature Energy, Journal Name: Nature Energy Journal Issue: 6 Vol. 3; ISSN 2058-7546

Publisher:: Nature Publishing Group

Country of Publication:: United States

Language:: English

References (36)

Efficient Methods for the Synthesis of 2-Hydroxyphenazine Based on the Pd-Catalyzed N -Arylation of Aryl Bromides Tietze, Mario; Iglesias, Alberto; Merisor, Elena Organic Letters, Vol. 7, Issue 8 https://doi.org/10.1021/ol050198y	journal	April 2005
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
Phenazine Natural Products: Biosynthesis, Synthetic Analogues, and Biological Activity Laursen, Jane Buus; Nielsen, John Chemical Reviews, Vol. 104, Issue 3 https://doi.org/10.1021/cr020473j	journal	March 2004
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
An aqueous, polymer-based redox-flow battery using non-corrosive, safe and low-cost materials Janoschka, Tobias; Martin, Norbert; Martin, Udo Nature, Vol. 527, Issue 7576, p. 78-81 https://doi.org/10.1038/nature15746	journal	October 2015
Material design and engineering of next-generation flow-battery technologies Park, Minjoon; Ryu, Jaechan; Wang, Wei Nature Reviews Materials, Vol. 2, Issue 1 https://doi.org/10.1038/natrevmats.2016.80	journal	November 2016
Preferential Solvation of an Asymmetric Redox Molecule Han, Kee Sung; Rajput, Nav Nidhi; Vijayakumar, M. The Journal of Physical Chemistry C, Vol. 120, Issue 49 https://doi.org/10.1021/acs.jpcc.6b09114	journal	December 2016
Thermodynamic properties of hydrated and ammoniated electrons Lepoutre, Gerard; Jortner, Joshua The Journal of Physical Chemistry, Vol. 76, Issue 5 https://doi.org/10.1021/j100649a015	journal	March 1972
Concentration-Dependent Dimerization of Anthraquinone Disulfonic Acid and Its Impact on Charge Storage Carney, Thomas J.; Collins, Steven J.; Moore, Jeffrey S. Chemistry of Materials, Vol. 29, Issue 11 https://doi.org/10.1021/acs.chemmater.7b00616	journal	May 2017
Predicting the potentials, solubilities and stabilities of metal-acetylacetonates for non-aqueous redox flow batteries using density functional theory calculations Kucharyson, J. F.; Cheng, L.; Tung, S. O. Journal of Materials Chemistry A, Vol. 5, Issue 26 https://doi.org/10.1039/C7TA01285C	journal	January 2017
Unraveling pH dependent cycling stability of ferricyanide/ferrocyanide in redox flow batteries Luo, Jian; Sam, Alyssa; Hu, Bo Nano Energy, Vol. 42 https://doi.org/10.1016/j.nanoen.2017.10.057	journal	December 2017
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
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
Efficient Synthesis of Substituted Dihydrotetraazapentacenes Seillan, Claire; Brisset, Hugues; Siri, Olivier Organic Letters, Vol. 10, Issue 18 https://doi.org/10.1021/ol801509v	journal	September 2008
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
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
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
Predicting Intrinsic Aqueous Solubility by a Thermodynamic Cycle Palmer, David S.; Llinàs, Antonio; Morao, Iñaki Molecular Pharmaceutics, Vol. 5, Issue 2 https://doi.org/10.1021/mp7000878	journal	January 2008
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
Towards High-Performance Nonaqueous Redox Flow Electrolyte Via Ionic Modification of Active Species Wei, Xiaoliang; Cosimbescu, Lelia; Xu, Wu Advanced Energy Materials, Vol. 5, Issue 1 https://doi.org/10.1002/aenm.201400678	journal	August 2014
Chemistry with ADF te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J. Journal of Computational Chemistry, Vol. 22, Issue 9, p. 931-967 https://doi.org/10.1002/jcc.1056	journal	January 2001
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
Nuclear magnetic resonance studies of the solvation structures of a high-performance nonaqueous redox flow electrolyte Deng, Xuchu; Hu, Mary; Wei, Xiaoliang Journal of Power Sources, Vol. 308 https://doi.org/10.1016/j.jpowsour.2015.12.005	journal	March 2016
Methanophenazine: Structure, Total Synthesis, and Function of a New Cofactor from Methanogenic Archaea Beifuss, Uwe; Tietze, Mario; Bäumer, Sebastian Angewandte Chemie International Edition, Vol. 39, Issue 14 https://doi.org/10.1002/1521-3773(20000717)39:14<2470::AID-ANIE2470>3.0.CO;2-R	journal	July 2000
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
Absolute Hydration Free Energy of the Proton from First-Principles Electronic Structure Calculations Zhan, Chang-Guo; Dixon, David A. The Journal of Physical Chemistry A, Vol. 105, Issue 51 https://doi.org/10.1021/jp012536s	journal	December 2001
Vanadium Flow Battery for Energy Storage: Prospects and Challenges Ding, Cong; Zhang, Huamin; Li, Xianfeng The Journal of Physical Chemistry Letters, Vol. 4, Issue 8 https://doi.org/10.1021/jz4001032	journal	March 2013
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
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
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
Accelerating Electrolyte Discovery for Energy Storage with High-Throughput Screening Cheng, Lei; Assary, Rajeev S.; Qu, Xiaohui The Journal of Physical Chemistry Letters, Vol. 6, Issue 2 https://doi.org/10.1021/jz502319n	journal	January 2015
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
Flow Batteries: Current Status and Trends Soloveichik, Grigorii L. Chemical Reviews, Vol. 115, Issue 20 https://doi.org/10.1021/cr500720t	journal	September 2015
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
Further conventions for NMR shielding and chemical shifts (IUPAC Recommendations 2008) Harris, Robin K.; Becker, Edwin D.; Cabral de Menezes, Sonia M. Pure and Applied Chemistry, Vol. 80, Issue 1 https://doi.org/10.1351/pac200880010059	journal	January 2008
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

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