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properties.34–37 Of particular interest, both of Laursen and Lacour groups reported the reversible oxidation and reduction electrochemical events of these stable carbenium ions.38,39 Similarly, our group recently reported the chemical reduction of a series of these cations leading to the isolation and characterization of the correponding neutral radical analog (DMQA•).40 We also demonstrated that nPr-DMQA+ tetrafluoroborate salt (labeled C+ in Figure 2a) is an efficient photocatalyst undergoing both chemical reduction and oxidation reactions via single electron transfer.41 Yet, the use of these electroactive compounds has never been reported in electrochemical energy storage. These helical carbenium ions are uniquely well-suited for RFB due to their rapid modular synthesis, electrochemical stability to wide voltage windows, and the presence of several reachable oxidation states. Herein, we report the study and use of nPr-DMQA+ (C+, Figure 2a) as both anolyte and catholyte for the development of a symmetrical non-aqueous ORFB, with a remarkable OCV of more than 2.1V and retaining more than 99% of its capacity after 740 cycles. Previous reports showed that C+ can be electrochemically reduced by one electron to form the neutral radical C● and oxidized by one electron to form the radical dication C●++ (Figure 2a).38–40 However, if these species are to be used for battery purposes, they must possess high stability during storage, charge, and discharge processes over extended periods of time in the solvent of choice.24 We previously reported that the electrochemical behavior of C+ in dichloromethane showed the reduced and oxidized species were electrochemically reversible, but the stability of the reduced species (C●) was limited to a few minutes.40 Cyclic voltammetry (CV) experiments in DMF showed higher stability of the C● radical, but poor reversibility was observed for the C++● 5PDF Image | Organic Redox Flow Battery Helical Carbeniun Ion
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