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Synthesis of (DHA)2 via electrochemical oxidation of DHA In a nitrogen-filled glovebox, an aqueous solution of 0.1 M synthetic DHA and 1.2 M KOH was prepared. An 80 μL aliquot was then dissolved in 720 μL of D2O within a sealed LPV NMR tube, and a 1H NMR spectrum was obtained within 1 hour (top spectrum). The DHA electrolyte was then electrochemically oxidized in a 5 cm2 flow cell vs DHAQ. When the oxidation current fell below 5 mA, the cell was stopped, and another 80 μL aliquot was taken for 1H NMR analysis. The result below indicates that DHA was completely converted to (DHA)2 by the electrochemical oxidation, as verified by comparison of the integrals of the 1H NMR signals with chemical shifts of 6-8 ppm, relative to that of a sodium methanesulfonate internal standard (δ 2.6 ppm, not shown in Fig. S12). Figure S12. 1H NMR spectra (500 MHz, D2O) relative to that of a sodium methanesulfonate internal standard (δ 2.6 ppm, not shown), of 10 mM synthetic DHA (top spectrum) with a 5% DHAQ impurity and of the DHA electrolyte after electrochemical oxidation (bottom spectrum), demonstrating conversion of DHA to (DHA)2. The total integral of the 1H NMR signals with chemical shifts of 6-8 ppm, indicates complete conversion of DHA to (DHA)2. 14PDF Image | Extending organic flow batteries via redox state management
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