Heavily fluorinated electronic polymers

Abstract

Building blocks, containing majority fluorine content by weight, for PPEs and PPVs have been synthesized. Some of the monomers were shown to give exclusively fluorous-phase soluble polymers, the syntheses of which were achieved by fluorous biphasic polymerization conditions. Perfluoroalkylated PPEs were found to have excellent fluorescence quantum yields and photophysical and chemical stability, and were used to demonstrate their capability in sensing electron-rich aromatic systems via fluorescence quenching. Perfluoroalkylated PPVs were shown to have poor solubility in both fluorous and non-fluorous solvents. Furthermore, the polymer displayed extremely high stability. Utilizing the fluorous solubility of perfluoroalkylated PPE, fluorescent fluorocarbon-in-water emulsions were achieved. When perfluoroalkylated carboxylate was used as the surfactant, emulsions with surfaces that could be modified via amide-bond forming reactions were obtained. When tagged with biotin, these emulsions showed large degrees of aggregation in the presence of streptavidin. The final chapter of this thesis describes an amide-bond forming reaction to attach gold nanoparticles selectively to the termini of single-walled carbon nanotubes utilizing surfactants to protect the sidewalls of nanotubes.