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methanesulfonate (δ 2.6 ppm) as an internal standard. Spectra were recorded on a Varian INOVA 500 MHz spectrometer unless otherwise specified. General information for synthesis 1H NMR and 13C NMR spectra were recorded on Varian INOVA 500 spectrometers unless otherwise specified. NMR spectra were recorded in solutions of deuterated dimethyl sulfoxide (DMSO-d6) with the residual dimethyl sulfoxide (δ 2.49 ppm for 1H NMR and δ 39.5 ppm for 13C NMR) taken as the internal reference and deuterated water (D2O) with the residual water (δ 4.79 ppm for 1H NMR) taken as the internal reference. All solvents and reagents were purchased from Sigma-Aldrich or Alfa Aesar and were used as received unless otherwise specified. High resolution LC-MS High-resolution LC-MS analysis was performed in the Small Molecule Mass Spectrometry Facility at Harvard University on a Bruker Impact II q-TOF with internal calibration sodium formate clusters. Liquid chromatography was performed on an Agilent 1290 Infinity HPLC using an Allure PFPP column (5 μm particle size, 150 x 2.1 mm) at a flow rate of 0.4 mL/min, and the following elution conditions were applied (solvent A = 0.1% v/v formic acid in water; solvent B = 0.1% v/v formic acid in acetonitrile): 95% solvent A for 2 min, a gradient increasing from 5% to 60% solvent B in solvent A over 13 min, a gradient increasing to 95% solvent B over 5 min, a gradient decreasing to 5% solvent B in solvent A over 0.1 min, and 95% solvent A for 4.9 min. The ESI mass spectra were recorded in negative ionization mode. Preparative-scale HPLC Liquid chromatography was performed using a Thermo Scientific Hypersil GOLD aQ column (5 μm particle size, 250 x 20 mm) at a flow rate of 10 mL/min, and the following elution conditions were applied (solvent A = 0.1% v/v formic acid in water; solvent B = 0.1% v/v formic acid in acetonitrile): 80% solvent A for 2 min, a gradient increasing from 20% to 70% solvent B in solvent A over 5 min, a gradient increasing to 85% solvent B over 10 min, a gradient increasing to 95% solvent B over 4 min, a gradient decreasing to 20% solvent B in solvent A over 1 min, and 80% solvent A for 2 min. The eluent fractions were collected and lyophilized for subsequent LC-MS confirmation. 2PDF Image | Extending organic flow batteries via redox state management
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