Ionic liquids and organic ionic plastic crystals promise to provide safer, nonflammable alternatives to the unstable organic electrolytes currently used in commercial batteries. However, the performance of ionic liquids and organic ionic plastic crystals as battery electrolytes has been hindered by poor lithium transport, in large part due to the formation of strong lithium-anion complexes. Similar ion coordination exists in ionic liquids containing dissolved sodium, magnesium, and calcium, suggesting that design of ionic liquids for sodium and multivalent battery chemistries will face similar challenges. In this talk, I will discuss our work on the design and characterization of novel ionic liquid-inspired organic electrolytes that leverage unique self-assembly properties of molecular diamond templates, called “diamondoids,” to promote selective redox ion transport. By leveraging the unique self-assembly properties of diamondoids, we show that metal cation-anion coordination can be reduced, and possibly removed, resulting in enhanced mobility of redox-active cations. Specifically, our investigation of electrolyte phase behavior, vibrational spectra, and magnetic environments demonstrates that metal salt solubility can remain high while metal cation-anion coordination is suppressed. Our results provide a new paradigm for enhancing redox species mobility in ionic liquid-derived electrolytes by engineering cation functional groups to enhance organic cation-anion interactions, suppress metal coordination, and leverage packing mismatches to enhance redox species mobility.