The synthesis and ring-opening metathesis polymerization of an amphiphilic redox-active norbornene

The synthesis and characterization of an amphiphilic, ferrocenyl-modified norbornene is reported. Linked together through a quaternary ammonium salt, the norbornenyl moiety makes this monomer susceptible to ring-opening metathesis polymerization (ROMP) using (PCy3)2RuCl2CHPh, while the ferrocenyl group allows for the incorporation of a redox-active group in the polymer backbone. The resulting polymers are soluble in both aqueous and organic media. Such polymers are important for the development of materials for electrochemically-based diagnostic applications. Cyclic voltammetry studies revealed that reversible redox waves are observed for both the monomer and polymer, although the E1/2 of the polymer is approximately 145 mV lower than that of the monomer, reflecting very different local environments.