Status and prospects of organic eletroactive species for aqueous organic redox flow batteries

doi:10.19799/j.cnki.2095-4239.2022.0009

Abstract

Abstract:

Aqueous organic redox flow batteries (AORFBs) represent a promising technology for large-scale storage and efficient utilization of renewable energy. In this paper, we thoroughly review organic electroactive species against four important performance parameters (energy density, power density, efficiency, and cycle life), based on the current status of AORFB research. For the different organic electroactive molecules, we clarify the effects on AORFB performance of solubility, potential, electron number, electrochemical redox kinetics, size, and chemical stability. The development of AORFBs shows favorable prospects relative to lithium iron phosphate batteries, lead carbon batteries, and all-vanadium redox flow batteries. AORFBs with energy density ≥30 Wh/L, maximum discharge power density ≥300 mW/cm², energy efficiency ≥80%, and capacity retention rate ≤0.05%/d can be expected to compete in the long-term energy storage market.

Key words: aqueous organic redox flow batteries, energy density, power density, efficiency, cycle life

CLC Number:

TQ 028.8

Kang PENG, Junmin LIU, Gonggen TANG, Zhengjin YANG, Tongwen XU. Status and prospects of organic eletroactive species for aqueous organic redox flow batteries[J]. Energy Storage Science and Technology, 2022, 11(4): 1246-1263.

Figures/Tables 15

References 61

1	MCGLADE C, EKINS P. The geographical distribution of fossil fuels unused when limiting global warming to 2 ℃[J]. Nature, 2015, 517: 187 -190 .
2	ERICKSON P, LAZARUS M, PIGGOT G. Limiting fossil fuel production as the next big step in climate policy[J]. Nature Climate Change, 2018, 8: 1037 -1043 .
3	HAEGEL N M, ATWATER H J, BARNES T, et al. Terawatt-scale photovoltaics: transform global energy[J]. Science, 2019, 364(6443): 836-838.
4	RINNE E, HOLTTINEN H, KIVILUOMA J, et al. Effects of turbine technology and land use on wind power resource potential[J]. Nature Energy, 2018, 3 (6 ): 494 -500.
5	LIU K, LIU Y Y, LIN D C, et al. Materials for lithium-ion battery safety[J]. Science Advances, 2018, 4(6): doi: 10.1126/sciadv.aas9820.
6	PARK M, RYU J, WANG W, et al. Material design and engineering of next-generation flow-battery technologies[J]. Nature Reviews Materials, 2017, 2: doi:10.1038/natrevmats.2016.80.
7	SINGH V, KIM S, KANG J, et al. Aqueous organic redox flow batteries[J]. Nano Research, 2019, 12(9): 1988-2001.
8	CAO J Y, TIAN J Y, XU J, et al. Organic flow batteries: Recent progress and perspectives[J]. Energy & Fuels, 2020, 34(11): 13384-13411.
9	LI Z J, LU Y C. Material design of aqueous redox flow batteries: Fundamental challenges and mitigation strategies[J]. Advanced Materials, 2020, 32(47): doi: 10.1002/adma.202002132.
10	KWON G, KO Y, KIM Y, et al. Versatile redox-active organic materials for rechargeable energy storage[J]. Accounts of Chemical Research, 2021, 54(23): 4423-4433.
11	FANG X T, LI Z G, ZHAO Y Y, et al. Multielectron organic redoxmers for energy-dense redox flow batteries[J]. ACS Materials Letters, 2022, 4(2): 277-306.
12	WINSBERG J, HAGEMANN T, JANOSCHKA T, et al. Redox-flow batteries: from metals to organic redox-active materials[J]. Angewandte Chemie (International Ed in English), 2017, 56(3): 686-711.
13	YANG Z J, GUO R, MALPASS-EVANS R, et al. Highly conductive anion-exchange membranes from microporous tröger's base polymers[J]. Angewandte Chemie (International Ed in English), 2016, 55(38): 11499-11502.
14	ZUO P P, LI Y Y, WANG A Q, et al. Sulfonated microporous polymer membranes with fast and selective ion transport for electrochemical energy conversion and storage[J]. Angewandte Chemie (International Ed in English), 2020, 59(24): 9564-9573.
15	JANOSCHKA T, MARTIN N, MARTIN U, et al. An aqueous, polymer-based redox-flow battery using non-corrosive, safe, and low-cost materials[J]. Nature, 2015, 527: 78 -81.
16	LIU T B, WEI X L, NIE Z M, et al. A total organic aqueous redox flow battery employing a low cost and sustainable methyl viologen anolyte and 4-HO-TEMPO catholyte[J]. Advanced Energy Materials, 2016, 6(3): doi: 10.1002/aenm.201501449.
17	JANOSCHKA T, MARTIN N, HAGER M D, et al. An aqueous redox-flow battery with high capacity and power: The TEMPTMA/MV system[J]. Angewandte Chemie (International Ed in English), 2016, 55(46): 14427-14430.
18	LIU Y H, GOULET M A, TONG L C, et al. A long-lifetime all-organic aqueous flow battery utilizing TMAP-TEMPO radical[J]. Chem, 2019, 5(7): 1861-1870.
19	HU B, DEBRULER C, RHODES Z, et al. Long-cycling aqueous organic redox flow battery (AORFB) toward sustainable and safe energy storage[J]. Journal of the American Chemical Society, 2017, 139(3): 1207-1214.
20	CHEN Q R, LI Y Y, LIU Y H, et al. Designer ferrocene catholyte for aqueous organic flow batteries[J]. ChemSusChem, 2021, 14(5): 1295-1301.
21	BEH E S, DE PORCELLINIS D, GRACIA R L, et al. A neutral pH aqueous organic-organometallic redox flow battery with extremely high capacity retention[J]. ACS Energy Letters, 2017, 2(3): 639-644.
22	ZHANG C K, NIU Z H, PENG S S, et al. Phenothiazine-based organic catholyte for high-capacity and long-life aqueous redox flow batteries[J]. Advanced Materials (Deerfield Beach, Fla), 2019, 31(24): doi: 10.1002/adma.201901052.
23	HUSKINSON B, MARSHAK M P", SUH C, et al. A metal-free organic-inorganic aqueous flow battery[J]. Nature, 2014, 505: 195 -198 .
24	LIN K X, CHEN Q, GERHARDT M R, et al. Alkaline quinone flow battery[J]. Science, 2015, 349: 1529-1532.
25	YANG Z J, TONG L C, TABOR D P, et al. Alkaline benzoquinone aqueous flow battery for large-scale storage of electrical energy[J]. Advanced Energy Materials, 2018, 8(8): doi:10.1002/aenm.201702056.
26	KWABI D G, LIN K X, JI Y L, et al. Alkaline quinone flow battery with long lifetime at pH 12[J]. Joule, 2018, 2(9): 1894-1906.
27	HU B, LUO J, HU M W, et al. A pH-neutral, metal-free aqueous organic redox flow battery employing an ammonium anthraquinone anolyte[J]. Angewandte Chemie (International Ed in English), 2019, 58(46): 16629-16636.
28	DEBRULER C, HU B, MOSS J, et al. Designer two-electron storage viologen anolyte materials for neutral aqueous organic redox flow batteries[J]. Chem, 2017, 3(6): 961-978.
29	HU B, TANG Y J, LUO J, et al. Improved radical stability of viologen anolytes in aqueous organic redox flow batteries[J]. Chemical Communications (Cambridge, England), 2018, 54(50): 6871-6874.
30	LIU Y H, LI Y Y, ZUO P P, et al. Screening viologen derivatives for neutral aqueous organic redox flow batteries[J]. ChemSusChem, 2020, 13(9): 2245-2249.
31	HUANG J H, HU S Z, YUAN X Z, et al. Radical stabilization of a tripyridinium-triazine molecule enables reversible storage of multiple electrons[J]. Angewandte Chemie (International Ed in English), 2021, 60(38): 20921-20925.
32	HUANG M B, HU S Z, YUAN X Z, et al. Five-membered-heterocycle bridged viologen with high voltage and superior stability for flow battery[J]. Advanced Functional Materials, 2022: doi:10.1002/adfm.202111744.
33	LUO J, HU B, DEBRULER C, et al. A π-conjugation extended viologen as a two-electron storage anolyte for total organic aqueous redox flow batteries[J]. Angewandte Chemie (International Ed in English), 2018, 57(1): 231-235.
34	HU S Z, LI T Y, HUANG M B, et al. Phenylene-bridged bispyridinium with high capacity and stability for aqueous flow batteries[J]. Advanced Materials (Deerfield Beach, Fla), 2021, 33(7): doi: 10.1002/adma.202005839.
35	LIANG Y, JING Y, GHEYTANI S, et al. Universal quinone electrodes for long cycle life aqueous rechargeable batteries[J]. Nature Materials, 2017, 16 (8 ): 841 -848.
36	ZHAO Q, ZHU Z, CHEN J. Molecular engineering with organic carbonyl electrode materials for advanced stationary and redox flow rechargeable batteries[J]. Advanced Materials (Deerfield Beach, Fla), 2017, 29(48): doi: 10.1002/adma.201607007.
37	HAN C P, LI H F, SHI R Y, et al. Organic quinones towards advanced electrochemical energy storage: Recent advances and challenges[J]. Journal of Materials Chemistry A, 2019, 7(41): 23378-23415.
38	KWON G, LEE K, LEE M H, et al. Bio-inspired molecular redesign of a multi-redox catholyte for high-energy non-aqueous organic redox flow batteries[J]. Chem, 2019, 5(10): 2642-2656.
39	CHAI J C, WANG X, LASHGARI A, et al. A pH-neutral, aqueous redox flow battery with a 3600-cycle lifetime: Micellization-enabled high stability and crossover suppression[J]. ChemSusChem, 2020, 13(16): 4069-4077.
40	GERKEN J B, ANSON C W, PREGER Y, et al. Comparison of quinone-based catholytes for aqueous redox flow batteries and demonstration of long-term stability with tetrasubstituted quinones[J]. Advanced Energy Materials, 2020, 10(20): doi:10.1002/aenm. 202000340.
41	ROMADINA E I, KOMAROV D S, STEVENSON K J, et al. New phenazine based anolyte material for high voltage organic redox flow batteries[J]. Chemical Communications (Cambridge, England), 2021, 57(24): 2986-2989.
42	XU J C, PANG S, WANG X Y, et al. Ultrastable aqueous phenazine flow batteries with high capacity operated at elevated temperatures[J]. Joule, 2021, 5(9): 2437-2449.
43	HUANG Z F, KAY C W M, KUTTICH B, et al. An "interaction-mediating" strategy towards enhanced solubility and redox properties of organics for aqueous flow batteries[J]. Nano Energy, 2020, 69: doi: 10.1016/j.nanoen.2020.104464.
44	ZHANG S Z, WANG G M, LU Y X, et al. The interactions between imidazolium-based ionic liquids and stable nitroxide radical species: a theoretical study[J]. The Journal of Physical Chemistry A, 2016, 120(30): 6089-6102.
45	DING Y, ZHANG C K, ZHANG L Y, et al. Insights into hydrotropic solubilization for hybrid ion redox flow batteries[J]. ACS Energy Letters, 2018, 3(11): 2641-2648.
46	ZHANG C K, ZHANG L Y, YU G H. Eutectic electrolytes as a promising platform for next-generation electrochemical energy storage[J]. Accounts of Chemical Research, 2020, 53(8): 1648-1659.
47	ZHANG C K, ZHANG L Y, DING Y, et al. Eutectic electrolytes for high-energy-density redox flow batteries[J]. ACS Energy Letters, 2018, 3(12): 2875-2883.
48	ZHANG C K, QIAN Y M, DING Y, et al. Biredox eutectic electrolytes derived from organic redox-active molecules: High-energy storage systems[J]. Angewandte Chemie (International Ed in English), 2019, 58(21): 7045-7050.
49	ZHOU M Y, CHEN Y, SALLA M, et al. Single-molecule redox-targeting reactions for a pH-neutral aqueous organic redox flow battery[J]. Angewandte Chemie (International Ed in English), 2020, 59(34): 14286-14291.
50	CHEN Y, ZHOU M Y, XIA Y H, et al. A stable and high-capacity redox targeting-based electrolyte for aqueous flow batteries[J]. Joule, 2019, 3(9): 2255-2267.
51	CHEN R Y. Toward high-voltage, energy-dense, and durable aqueous organic redox flow batteries: role of the supporting electrolytes[J]. ChemElectroChem, 2019, 6(3): 603-612.
52	SUN P, LIU Y H, LI Y Y, et al. 110th anniversary: Unleashing the full potential of quinones for high performance aqueous organic flow battery[J]. Industrial & Engineering Chemistry Research, 2019, 58(10): 3994-3999.
53	HU B, SEEFELDT C, DEBRULER C, et al. Boosting the energy efficiency and power performance of neutral aqueous organic redox flow batteries[J]. Journal of Materials Chemistry A, 2017, 5(42): 22137-22145.
54	XIAO Y, HU L, GAO L, et al. Enabling high Anion-selective conductivity in membrane for high-performance neutral organic based aqueous redox flow battery by microstructure design[J]. Chemical Engineering Journal, 2022, 432: doi:10.1016/j.‍cej. 2021.134268.
55	KWABI D G, JI Y L, AZIZ M J. Electrolyte lifetime in aqueous organic redox flow batteries: A critical review[J]. Chemical Reviews, 2020, 120(14): 6467-6489.
56	JI Y L, GOULET M A, POLLACK D A, et al. A phosphonate-functionalized quinone redox flow battery at near-neutral pH with record capacity retention rate[J]. Advanced Energy Materials, 2019, 9(12): doi: 10.1002/aenm.201900039.
57	WU M, JING Y, WONG A A, et al. Extremely stable anthraquinone negolytes synthesized from common precursors[J]. Chem, 2020, 6(6): 1432-1442.
58	GOULET M A, TONG L C, POLLACK D A, et al. Extending the lifetime of organic flow batteries via redox state management[J]. Journal of the American Chemical Society, 2019, 141(20): 8014-8019.
59	HU B, HU M W, LUO J, et al. A stable, low permeable TEMPO catholyte for aqueous total organic redox flow batteries[J]. Advanced Energy Materials, 2021: doi: 10.1002/aenm.202102577.
60	LUO J, HU B, HU M W, et al. Status and prospects of organic redox flow batteries toward sustainable energy storage[J]. ACS Energy Letters, 2019, 4(9): 2220-2240.
61	TAN R, WANG A, MALPASS-EVANS R, et al. Hydrophilic microporous membranes for selective ion separation and flow-battery energy storage[J]. Nature Materials, 2020, 19(2): 195-202.

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