Non-aqueous organic redox flow batteries have been suggested as an alternative to aqueous vanadium redox flow batteries due to the ability of using earth abundant carbon materials. However, rapid electrolyte crossover between anolyte and catholyte is a problem. Bipolar redox-active molecules are single molecules that undergo both anode and cathode redox reactions and they are an option for addressing this crossover problem. The unique redox chemistry of bipolar redoxmers is commensurate to vanadium species, but enable greater design flexibility and potentially better properties than are otherwise observed. However, there are complex tradeoffs in their properties. Balancing these properties have been incredibly challenging. As such, this talk will discuss the rational design of bipolar redoxmers and the tradeoffs needed to optimize performance. Our studies revealed that the oscillating properties observed are a result of conformation-related interactions, suggesting the critical role of structural order in bipolar redoxmer systems. This talk will also discuss ion exchange polymer strategies for minimizing crossover in RFBs.