Elastomers without reinforcement are too weak and soft to meet the requirements of practical applications. To achieve the necessary strength and stiffness, particulate fillers are used to reinforce thermoset rubber. For thermoplastic elastomers, microphase-separated hard domains play the role of stiffening and strengthening the elastomer. Our group recently reported reactive supramolecular fillers based on [beta]-alanine oligomers. This thesis focuses on the use of reactive fillers containing a mercaptan tail and an ionic head as supramolecular filler for cured rubbers. The reactive functional groups of the fillers can form covalent bond with elastomers' backbone. After the reaction, the elastomer becomes an ionomer, which is defined as polymers with bonded ionic groups that are used under conditions where the salt species are in condense state. Since the polar ionic groups are incompatible with the low nonpolar polymer, microscopic phase separation will occur. The alkyl chain is attached to the ionic species to improve the compatibility. Ionic nanodomains formed by the polar ionic moieties are anticipated. The ion interaction within ionic clusters can serve as physical crosslinks. The reversibility of the supramolecular interaction offers a mechanism for energy dissipation that should increase mechanical properties of rubber. The extent of reinforcement and the supramolecular structure of ion-containing filler are studied.