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Identification of DHA The capacity-limiting electrolyte utilized in the experiment of which results are depicted in Fig. S2 was collected after several days of further cycling with a +200 mV oxidation overpotential. Initial HPLC-MS analysis suggested primarily one major compound in addition to DHAQ, namely 2,6-dihydroxyanthrone (DHA). To verify the identification of DHA as the major side-product of DHAQ cell cycling at this potential, DHA was synthesized (Fig. S3) and confirmed to have the same retention time in HPLC-MS (Fig. S4). In addition, NMR spectroscopy was also performed on a mixture of synthesized DHA and DHAQ to simulate the cycled electrolyte. The NMR spectrum of DHA-spiked DHAQ (Fig. S5) qualitatively matches the spectrum of discharged cycled DHAQ (Fig. S2b). a b Figure S3. (a) Chemical synthesis of DHA. (b) 1H NMR spectrum of synthetic DHA in DMSO-d6. 2,6-Dihydroxyanthrone (DHA). The synthesis of DHA (Fig. S3a) was carried out according to a reported procedure2 with modifications. 2,6-dihydroxyanthraquinone (DHAQ, 2.40 g, 10.0 mmol) and stannous chloride (15.2 g, 80.0 mmol) were refluxed for 7 h in 80 mL of concentrated hydrochloric acid. The resulting solution was cooled to room temperature, and the precipitate was collected by vacuum filtration. The collected solid was washed with DI water. The product was dried in vacuo to afford 2.20 g pale yellow powder (97% yield). 1H NMR (600 MHz, DMSO-d6) δ 10.41 (s, 1H), 9.69 (s, 1H), 8.03 (d, J = 8 Hz, 1H), 7.51 (d, J = 3 Hz, 1H), 7.35 (d, J = 8 Hz, 1H), 7.06 (dd, J = 8 Hz, 3 Hz, 1H), 6.87 (m, 2H), 4.22 (s, 2H) HRMS (ESI) m/z: calcd for C14H9O3 [M-H]-, 225.0552; found, 225.0556. 5PDF Image | Extending organic flow batteries via redox state management
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