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in Scheme 2. During the reduction (charging) process, the dication viologen molecule receives one electron to give a cation radical, which is further reduced at a more negative potential to form neutral bipyridinylidene. Methyl viologen dichloride (MV, Entry1 in Table 3) has been widely explored in AORFBs (30, 68). It displays high solubility in water (3 M), corresponding to a theoretical capacity of 80.4 Ah/L for one-electron redox process. Increasing the size of nonpolar substituents on both distal N atoms enhances the hydrophobicity, lowering the solubility in an aqueous medium. Scheme 2. The redox steps of viologens. MV is prone to side reactions in aqueous condition (25). Dimerization of reduced viologen cation radical gave viologen dimer (Scheme 3a). One-electron reduced MV can be converted back to original MV in the presence of O2, but generate hydroxide ions. The OH− reacts with MV and yields 1-methyl-(4,4′-bipyridin)-1-ium chloride and formaldehyde (Scheme 3b). In addition, some one- electron reduced MV could also undergo disproportionation to form the original MV and the doubly reduced bipyridinylidene. The doubly reduced bipyridinylidene can be irreversibly protonated to form a series of redox-inactive species (Scheme 3c). Scheme 3. Proposed decomposition mechanism of MV. Increasing the steric hindrance of viologens with ionic groups, such as -NR3+ and -SO3H, can suppress dimer formation via an electrostatic repulsion mechanism. Aziz et al. synthesized bis(3- 15 Qin and Fan; Clean Energy Materials ACS Symposium Series; American Chemical Society: Washington, DC, 2020.PDF Image | Electroactive Materials Next-Generation Redox Flow Batteries
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