Nonaqueous redox flow batteries are a promising technology for grid-scale energy storage, however, their commercial success relies on identifying redox active materials that exhibit extreme potentials, high solubilities in all states of charge, and long cycling stabilities. Meeting these requirements has been particularly challenging for molecules capable of storing negative charge. Within this context, the symmetric tetrazines remain unexplored despite their unique structural properties that enable them to meet these challenges. Herein, we prepared s-tetrazines substituted with methyl, methoxy, and thiomethyl substituents and evaluated their electrochemical properties, solubility, and cycling stability. These studies revealed that 3,6-dimethoxy-s-tetrazine undergoes a reversible one-electron reduction to generate a soluble (>0.5 M in electrolyte/solvent) and stable (t1/2 > 1240 h) radical anion. When implemented in a lab-scale flow battery, it exhibited a relatively slow capacity fade of 13% over 100 cycles (38 h). Given their uncommonly high solubility and cycling stability, we believe that s-tetrazine derivatives should be further explored for non-aqueous redox flow batteries. 5-Amino-1H-pyrazole-3-carboxylic acid uses 55685-58-0 structure PMID:23795974
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