High Energy Density Aqueous Flow Battery Utilizing Extremely Stable, Branching-Induced High-Solubility Anthraquinone near Neutral pH

An anthraquinone featuring a chiral carboxylate-capped methyl-branched side chain with an ether linkage, 2,2 '- ((9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(oxy))- dipropionicacid (2,6-D2PEAQ), was synthesized and evaluated for use in aqueous redox flow batteries. It was found to have an extraordinary solubility of 2 M (4 M electrons), corresponding to a theoretical volumetric capacity of 107.2 Ah/L for the negative electrolyte, which is 10 times that of its unbranched counterpart. The 2,6-D2PEAQ molecule demonstrated stability against thermal decomposition and was extremely stable under cell cycling conditions. A capacity fade rate of 0.02%/day over 14 days was demonstrated in a 1.1 M 2,6-D2PEAQ nearly capacity-balanced cell when paired with a ferro-/ferricyanide posolyte at pH 7. Compared to other aqueous redox-active organic molecules, its demonstrated fade rate is lower than that of any molecule with a demonstrated volumetric capacity of >= 55 Ah/L, and its volumetric capacity is greater than that of any molecule with a demonstrated fade rate of <= 0.5%/day.