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## Creator

Ning Lu, Shiyao Ju, Daniel Willimetz, Shengming Tang, Abhishek Khetan

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[A data-driven elucidation of the challenges in designing stable quinone derivatives for aqueous organic redox flow batteries: correlations between thermodynamics of chemical degradation and energy capacity metrics](https://mdr.nims.go.jp/datasets/194eeebf-865e-4afd-bcc5-f96ab57019ca)

## Fulltext

Supplementary information  A data-driven elucidation of the challenges in designing stable quinone derivatives for aqueous organic redox flow batteries: correlations between thermodynamics of chemical degradation and energy capacity metrics Ning Lua, Shiyao Jua, Daniel Willimetza,b, Shengming Tanga, Abhishek Khetana*  a MODES, The Integrated Fuel & Chemical Science Centre, RWTH Aachen University, 52062 Aachen, Germany bFraunhofer Institute for Algorithms and Scientific Computing SCAI, Fraunhofer-Gesellschaft, Schloss Birlinghoven 1, 53757 Sankt Augustin, Germany *Corresponding author: Abhishek Khetan; Email: askhetan@modes.rwth-aachen.de    Explanation of the abbreviations used in the below tables: SMILES: simplified molecular-input line-entry system  DFT: density functional theory  R2: the coefficient of fit  RMSE: the root mean squared error MSE: the mean squared error MAE: the mean absolute error RMSD: root mean square deviation Table S1.  The 35 SMIRKS templates used to represent the eight reaction categories considered in this work, comprising seven degradation reactions and the main electrochemical redox reaction. SMIRKS1 : [O:0]=[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]=[C:7]-1>>[O:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O:5]):[c:6]:[c:7]:1  SMIRKS 2 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[C:6]=[C:7]-1>>[O:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O:5]):[c:6]:[c:7]:1  SMIRKS 3 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[c:6]:[c:7]-1>>[O:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O:5]):[c:6]:[c:7]:1  SMIRKS 4 : [O:0]=[c:1]1:[c:2]=[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1>>[O:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O:5]):[c:6]:[c:7]:1   SMIRKS 5 : [O:0]=[c:1]1:[c:2]:[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1>>[O:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O:5]):[c:6]:[c:7]:1  SMIRKS 6 : [O:0]=[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]=[C:7]-1>>[O-:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O-:5]):[c:6]:[c:7]:1  SMIRKS 7 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[C:6]=[C:7]-1>>[O-:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O-:5]):[c:6]:[c:7]:1  SMIRKS 8 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[c:6]:[c:7]-1>>[O-:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O-:5]):[c:6]:[c:7]:1  SMIRKS 9 : [O:0]=[c:1]1:[c:2]=[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1>>[O-:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O-:5]):[c:6]:[c:7]:1  SMIRKS 10 : [O:0]=[c:1]1:[c:2]:[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1>>[O-:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O-:5]):[c:6]:[c:7]:1  SMIRKS 11 : [O:0]=[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]=[C:7]-1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]=[C:3]-[C:4](-[O:5])(-[O:8])-[C:6]=[C:7]-1  SMIRKS 12 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[C:6]=[C:7]-1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]:[C:3]-[C:4](-[O:5])(-[O:8])-[C:6]=[C:7]-1   SMIRKS 13 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[c:6]:[c:7]-1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]:[C:3]-[C:4](-[O:5])(-[O:8])-[C:6]:[C:7]-1  SMIRKS14 : [O:0]=[c:1]1:[c:2]=[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1.[O;H2;+0:8]>>[O:0]=[c:1]1:[c:2]=[c:3]:[c:4](-[O:5])(-[O:8]):[c:6]:[c:7]:1  SMIRKS 15 : [O:0]=[c:1]1:[c:2]:[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]:[C:3]-[C:4](-[O:5])(-[O:8])-[C:6]=[C:7]-1  SMIRKS 16 : [C;H0;D3;+0:0]-[S:1](-[O:2])(=[O:3])=[O:4]>>[C;H0;D3;+0:0].[S:1](-[O:2])(=[O:3])=[O:4]  SMIRKS 17 : [c:0]-[S:1](-[O:2])(=[O:3])=[O:4]>>[c:0].[S:1](-[O:2])(=[O:3])=[O:4]  SMIRKS 18 : [O:0]=[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]=[C;D2;+0:7]-1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]=[C:3]-[C:4](-[O:5])=[C:6]-[C:7]-1-[O:8]  SMIRKS 19 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[C:6]=[C;D2;+0:7]-1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]=[C:3]-[C:4](-[O:5])=[C:6]-[C:7]-1-[O:8]  SMIRKS 20 : [O:0]=[c:1]1:[c:2]=[c:3]:[c:4](=[O:5]):[c:6]:[c;H1;D2;+0:7]:1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]=[C:3]-[C:4](-[O:5])=[C:6]-[C:7]-1-[O:8]  SMIRKS 21 :  [O:0]=[c:1]1:[c:2]:[c:3]:[c:4](=[O:5]):[c:6]:[c;H1;D2;+0:7]:1.[O;H2;+0:8]>>[O:0]=[C:1]1-[C:2]=[C:3]-[C:4](-[O:5])=[C:6]-[C:7]-1-[O:8]   SMIRKS 22 : [C:0]-[C:1](=[O:2])-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c;H1;D2;+0:8]:1.[O;H2;+0:9]>>[C:0]/[C:1](-[O:2])=[C:3]1\[C:4]=[C:5]-[C:6]=[C:7]-[C:8]-1-[O:9]  SMIRKS 23 : [c:0]-[C:1](=[O:2])-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c;H1;D2;+0:8]:1.[O;H2;+0:9]>>[C:0]/[C:1](-[O:2])=[C:3]1\[C:4]=[C:5]-[C:6]=[C:7]-[C:8]-1-[O:9]  SMIRKS 24 : [c:0]:[c:1](=[O:2]):[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c;H1;D2;+0:8]:1.[O;H2;+0:9]>>[C:0]/[C:1](-[O:2])=[C:3]1\[C:4]=[C:5]-[C:6]=[C:7]-[C:8]-1-[O:9]  SMIRKS 25 : [O:0]=[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]=[C:7]-1>>[O:0]=[c:1]1-[c:2]=[c:3]-[c:4]-[c:6]=[c:7]-1.[O;H2;+0:5]  SMIRKS 26 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[C:6]=[C:7]-1>>[O:0]=[c:1]1-[c:2]:[c:3]-[c:4]-[c:6]=[c:7]-1.[O;H2;+0:5]  SMIRKS 27 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](=[O:5])-[c:6]:[c:7]-1>>[O:0]=[c:1]1-[c:2]:[c:3]-[c:4]-[c:6]:[c:7]-1.[O;H2;+0:5]   SMIRKS 28 : [O:0]=[c:1]1:[c:2]=[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1>>[O:0]=[C:1]1-[c:2]:[c:3]-[C:4]-[C:6]=[C:7]-1.[O;H2;+0:5]  SMIRKS 29 : [O:0]=[c:1]1:[c:2]:[c:3]:[c:4](=[O:5]):[c:6]:[c:7]:1>>[O:0]=[C:1]1-[c:2]:[c:3]-[C:4]-[C:6]=[C:7]-1.[O;H2;+0:5]  SMIRKS 30 : [O;v2;+0:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O;v2;+0:5]):[c:6]:[c:7]:1>>[O:0]-[C:1]1=[C:2]-[C:3]-[C:4](=[O:5])-[C:6]=[C:7]-1  SMIRKS 31 : [O;v2;+0:0]-[c:1]1:[c;D3;+0:2]:[c;D3;+0:3]:[c:4](-[O;v2;+0:5]):[c:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1:2>>[O:0]-[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]2-[C:7]=[C:8]-[C:9]=[C:10]-[C:11]=1-2    SMIRKS 32 : [O:0]=[C:1]1-[C:2]=[C:3]-[C:4](-[O:5])=[C:6]-[C:7]-1>>[O:0]=[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]-[C:7]-1  SMIRKS 33 : [O:0]=[C:1]1-[c:2]:[c:3]-[C:4](-[O:5])=[C:6]-[C:7]-1>>[O:0]=[C:1]1-[C:2]=[C:3]-[C:4](=[O:5])-[C:6]-[C:7]-1  SMIRKS 34 : [O-:0]-[c:1]1:[c:2]:[c:3]:[c:4](-[O-:5]):[c:6]:[c:7]:1>>[O;H0;+0:0]=[c:1]1-[c:2]=[c:3]-[c-:4]-[c:6]=[c:7]-1.[O;H2;+0:5]  SMIRKS 35 : [O:0]=[c:1]1:[c:2]:[c:3]:[cH-:4]:[c:5]:[c:6]:1.[O:7]=[c:8]1:[c:9]:[c:10]:[cH-:11]:[c:12]:[c:13]:1>>[O:0]=[C:1]1-[C:2]=[C:3]-[C;H1;+0:4](-[C;H1;+0:11]2-[C:12]=[C:13]-[C:8](=[O:7])-[C:9]=[C:10]-2)-[C:5]=[C:6]-1    Figure S1. The simulation between the free energy and the redox potential in experiments.         Figure S2. Redox potential property relationships. The reduction potential depends on both the redox pattern (the relative positions of the carbonyl groups) and the functional groups. The numbers refer to the molecules of the redox pattern and correspond to the labels in Fig. 1. The median of each set of data is indicated with a black line. The regions bounded by the colours represent the range of the 5th and 95th percentiles of reduction potentials. The lines extend out to the maximum and minimum reduction potential for each substitution and ketone  Figure S3. The relationship between the predicted redox potential and the Gibbs free energy of Proto-desulfonation.      Figure S4. Effect of functional groups on stability based on core structure under Michael addition mechanisms     Figure S5. Effect of functional groups on stability based on core structure under Gem-Diol Formation mechanisms.   Figure S6. Effect of functional groups on stability based on core structure under the Anthrone formation mechanism.       Figure S7. Effect of functional groups on stability based on core structure under the Tautomerization mechanism.     Figure S8. Effect of functional groups on stability based on core structure under the Disproportionation mechanism.     Figure S9. Effect of functional groups on stability based on core structure under the Dimerization mechanism.          Figure S10. The relationship between the solvation reaction Gibbs free energy and the reaction Gibbs free energy of the six degradation mechanisms.  Figure S11. Structures of literature compounds used for validation. Label colour indicates relative cycling stability reported experimentally (green: more stable; red: less stable); see Table S3 for conditions and performance metrics.   Figure S12. Experimental Validation of Theoretical Predictions: The relationship between the stability and the redox potential with the structures of the experimental points.   Table S2. A summary of 2D structures, SMILES representations, experimental redox potential(V versus SHE) of the compounds. # Molecule SMILES 𝐸𝑒𝑥𝑝°  (V vs. SHE) Ref. 1  O=C1C(=O)C=C C=C1 0.831  [1] 2  O=C1C(=O)C=Cc (c12)cccc2 0.547 [1] 3  O=C1C=CC(=O) C=C1 0.699 [1] 4  O=C1C=CC(=O)c (c12)cccc2 0.470 [1] 5  c1cccc(c12)C(=O) c3c(C2=O)cccc3 0.090 [1] 6  c1cccc(c12)c3c(C (=O)C2=O)cccc3 0.442 [1] 7  c1cccc(C2=O)c1C (=O)c(c23)cc(cc3) S(=O)(=O)O 0.187 [2] 8  c1cccc(c12)C(=O) C(=C(C2=O)O)C C=C(C)C 0.333 [3] 9  c1cccc(c12)C(=O) C(O)=CC2=O 0.308  [3] 10  c1c(O)ccc(c12)C( =O)c3c(C2=O)ccc (c3)O 0.039 [3] 11  Oc1c(O)ccc(c12) C(=O)c3c(C2=O) cccc3 0.005 [3] 12  OC1=CC(=O)C(O )=CC1=O 0.382 [3] 13  O=C1C(F)=C(F)C (=O)C(F)=C1F 0.707 [3] 14  O=C1C(O)=C(Cl) C(=O)C(=C1Cl)O 0.394 [3] 15  O=C1C(Cl)=C(Cl )C(=O)C(Cl)=C1 Cl 0.700 [3] 16  c1ccc(S(=O)(=O) O)c(c12)C(=O)c3 c(C2=O)cccc3S(= O)(=O)O 0.206 [4] 17  c1ccc(S(=O)(=O) O)c(c12)C(=O)c3 c(C2=O)c(S(=O)( =O)O)ccc3 0.239 [4] 18  O=S(=O)(O)c(cc1 )cc(c12)C(=O)c3c (C2=O)cc(S(=O)( =O)O)cc3 0.228 [4] 19  O=S(=O)(O)c(cc1 )cc(c12)C(=O)C= CC2=O 0.534 [4] 20  O=C1C=CC(=O) C(O)=C1 0.594 [4] 21  CC1=CC(=O)C= CC1=O 0.641 [4] 22  O=C1C=CC(=O) C(Cl)=C1 0.71 [4] 23  O=c1c(=O)c(S(= O)(=O)O)cc(c2= O)c1c(=O)c(c23)c ccc3 1.21 [4] 24  c1cccc(c12)c(=O) c3c(c2=O)c(=O)c( SCCS(=O)(=O)O) c(c3=O)SCCS(=O )(=O)O 1.08 [4] 25  O=c1c(S(=O)(=O )O)cc(=O)c(c2=O )c1c(=O)c(c23)cc cc3 1.05 [4] Table S3. Summary of experimental redox couples and performance metrics of AORFBs from literature ID RFB                                               positive/electrolyte/negative pH Current density Cycle no. Coulombic efficiency Capacity fading rate Capacity retention at cycle no. Energy efficiency at cycle no. Loss in discharge capacity  Discharge capacity  Charge efficiency 1[5] 2Cl-NQ/1 M H2SO4/PTCDA(perylene-3,4,9,10-tetracarboxylic dianhydride) 2.78 1 Ag-1 1800 100%  98.60%     2[6] 1,4-dihydroxyphenylsulfonate potassium (HQS)/Na2SO4/9,10-anthraquinone-2,7-disulfonic salt (2,7-AQDS) 7 60 mAcm-2 120 96.00%   56%    3[7]  K4Fe(CN)6/KOH/1,4-dihydroxy-2-carboxymethyl-9,10-anthraquinone (1,4-CDHAQ) 13 40 mAcm-2 2500 97% 0.28% / day 55% 82%    ID RFB                                               positive/electrolyte/negative pH Current density Cycle no. Coulombic efficiency Capacity fading rate Capacity retention at cycle no. Energy efficiency at cycle no. Loss in discharge capacity  Discharge capacity  Charge efficiency 4[8] K3Fe(CN)6([Fe(CN)6]3−/4)/KOH/ 1,5-dihydroxyanthraquinone(1,5-DHAQ-PAQS) 14 80 mAcm-2 500 99%  94.30% 48.00%    5[9] ferrocyanide/NaOH/ sodium 3,3′,3′′,3′′′-((9,10-anthraquinone-2,6diyl)bis(azanetriyl))tetrakis(propane-1-sulfonate)(2,6-N-TSAQ) 14 40 mAcm−2 900 99.9 % 0.025%/day        6a[5] 2,6-dimethyl-3,5-bis(morpholino methylene)benzene-1,4-diol (asym-O-5)/H2SO4/2,6-dimethyl-3,5-bis(morpholinomethylene)benzene-1,4-diol (asym-O-5) 1.54 20 mAcm-2 300  1.8% /day      ID RFB                                               positive/electrolyte/negative pH Current density Cycle no. Coulombic efficiency Capacity fading rate Capacity retention at cycle no. Energy efficiency at cycle no. Loss in discharge capacity  Discharge capacity  Charge efficiency  6b[5] 2,5-dimethyl-3,6-bis(morpholino methylene)benzene-1,4-diol (O-5)/H2SO4/2,5-dimethyl-3,6-bis(morpholinomethylene)benzene-1,4-diol (O-5) 1.54 50 mAcm-2 300  0.87% /day       6c[5] 2,3,5-trimethyl-6-(morpholino methylene)benzene-1,4-diol (O-1)/H2SO4/2,3,5-trimethyl-6-(morpholinomethylene)benzene-1,4-diol (O-1) 1.54 50 mAcm-2 300  7.3% /day       6d[5] 2,5-bis(morpholinomethylene)benzene-1,4-diol (O-3)/H2SO4/2,5-1.54 50 mAcm-2 300  52.7% /day      ID RFB                                               positive/electrolyte/negative pH Current density Cycle no. Coulombic efficiency Capacity fading rate Capacity retention at cycle no. Energy efficiency at cycle no. Loss in discharge capacity  Discharge capacity  Charge efficiency bis(morpholinomethylene)benzene-1,4-diol (O-3) 7a[10] a tetrasubstituted quinone containing four sulfonated thioether substituents/H2SO4/anthraquinone-2,7-disulfonate (AQDS) 2.75 50 mAcm-2 50    75% 2% 90% 100% 7b[10]  4,5-Dihydroxy-1,3-benzenedisulfonate/H2SO4/anthraquinone-2,7-disulfonate (AQDS) 2.75 50 mAcm-2 50    50% 48% 50% 95% 7c[10] para-Hydroxy benzenesulfonic acid/H2SO4/anthraquinone-2,7-disulfonate (AQDS) 2.75 50 mAcm-2 50    40% 52% 30% 95% ID RFB                                               positive/electrolyte/negative pH Current density Cycle no. Coulombic efficiency Capacity fading rate Capacity retention at cycle no. Energy efficiency at cycle no. Loss in discharge capacity  Discharge capacity  Charge efficiency 7d[10] 2,4-Dimethyl-3-sulfo-1,5-dihydroxybenzene/H2SO4/anthraquinone-2,7-disulfonate (AQDS) 2.75 50 mAcm-2 50    70% 40% 20% 99.80% 8[11] ferrocyanide/KCl/2-2PEAQ 7 40  mAcm-2 2000  ≈100% 0.09% /day       ferrocyanide/KOH/2-2PEAQ 14 40  mAcm-2 800  ≈100% 0.05% /day       9[9] ferro-/ferricyanide//2,2′-((9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(oxy))dipropionic acid (2,6-D2PEAQ) 7 100 mAcm-2 170 99.70% 0.02% /day       10[12] potassium ferrocyanide//4,4′-((9,10-anthraquinone-2,6-12 100 mAcm-2 880  0.01% /day      ID RFB                                               positive/electrolyte/negative pH Current density Cycle no. Coulombic efficiency Capacity fading rate Capacity retention at cycle no. Energy efficiency at cycle no. Loss in discharge capacity  Discharge capacity  Charge efficiency diyl)dioxy)dibutyrate (2,6-DBEAQ)  11[13]  ferri/ferrocyanide//2,6-DPPEAQ, (((9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(oxy))bis(propane-3,1-diyl))bis(phosphonic acid) 9 100 mAcm-2 480 99.90% 0.014% /day  65%    15[14] potassium ferrocyanide/NaOH/2,3-dihydroxylated anthraquinone(2,3-DHAQ) 14 50 mAcm-2 3000 100.00% 0.8% / day  75%    19[15] ferrocyanide/NaOH/3-NH2-2-2PEAQ  14 80  >98% 0.01% / day  >70%     Reference: [1] Wass JRTJ, Ahlberg E, Panas I, et al. Quantum Chemical Modeling of the Reduction of Quinones. The Journal of Physical Chemistry A. 2006;110(5). [2] Gerhardt MR, Tong L, Gómez‐Bombarelli R, et al. Anthraquinone Derivatives in Aqueous Flow Batteries. Advanced Energy Materials. 2016;7(8). [3] Wedege K, Drazevic E, Konya D, et al. Organic Redox Species in Aqueous Flow Batteries: Redox Potentials, Chemical Stability and Solubility. Sci Rep. 2016;6:39101. [4] Tabor DP, Gómez-Bombarelli R, Tong L, et al. 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Highly Stable, Low Redox Potential Quinone for Aqueous Flow Batteries**. Batteries & Supercaps. 2022;5(6). [10] Kwabi DG, Lin K, Ji Y, et al. Alkaline Quinone Flow Battery with Long Lifetime at pH 12. Joule. 2018;2(9):1894-1906. [11] Guiheneuf S, Godet-Bar T, Fontmorin JM, et al. A new hydroxyanthraquinone derivative with a low and reversible capacity fading process as negolyte in alkaline aqueous redox flow batteries. Journal of Power Sources. 2022;539. [12] Ding Y, Li Y, Yu G. Exploring Bio-inspired Quinone-Based Organic Redox Flow Batteries: A Combined Experimental and Computational Study. Chem. 2016;1(5):790-801. [13] Wu M, Jing Y, Wong AA, et al. Extremely Stable Anthraquinone Negolytes Synthesized from Common Precursors. Chem. 2020;6(6):1432-1442. [14] Yang X, Garcia SN, Janoschka T, et al. Novel, Stable Catholyte for Aqueous Organic Redox Flow Batteries: Symmetric Cell Study of Hydroquinones with High Accessible Capacity. Molecules. 2021;26(13). [15] Alfaraidi AM, Xi D, Ni N, et al. An Extremely Stable and Soluble NH2-Substituted Anthraquinone Electrolyte for Aqueous Redox Flow Batteries. ACS Applied Energy Materials. 2023;6(24):12259-12266.   Reference: