Aqueous Solubility of Organic Compounds for Flow Battery Applications: Symmetry and Counter Ion Design to Avoid Low-Solubility Polymorphs.

Flow batteries can play an important role as energy storage media in future electricity grids. Organic compounds, based on abundant elements, are appealing alternatives as redox couples for redox flow batteries. The straightforward scalability, the independence of material sources, and the potentially attractive price motivate researchers to investigate this technological area. Four different benzyl-morpholino hydroquinone derivatives were synthesized as potential redox active species. Compounds bearing central symmetry were shown to be about an order of magnitude less soluble in water than isomers without central symmetry. Counter ions also affected solubility. Perchlorate, chlorate, sulfate and phosphate anions were investigated as counter ions. The formations of different polymorphs was observed, showing that their solubility is not a function of their structure. The kinetics of the transformation can give misleading solubility values according to Ostwald's rule. The unpredictability of both the kinetics and the thermodynamics of the formation of polymorphs is a danger for new organic compounds designed for flow battery applications.