The main drawback of organic electrode materials is their solubility in the electrolyte, leading to the shuttle effect. Using N,N'-dimethylphenazine (DMPZ) as a highly soluble cathode material, and its PF and triflimide salts as models for its first oxidation state, a poor correlation was found between solubility and battery operability. Extensive electrochemical experiments suggest that the shuttle effect is unlikely to be mediated by molecular diffusion as commonly understood, but rather by electron-hopping via the electron self-exchange reaction based on spectroscopic results. These findings led to two counter-strategies to prevent the hopping process: the pre-treatment of the anode to form a solid-electrolyte interface and using DMPZ salt rather than neutral DMPZ as the active material. These strategies improved coulombic efficiency and capacity retention, demonstrating that solubility of organic materials does not necessarily exclude their applications in batteries.
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