Heterophase polymerizations have gained increasing attention in the past decades, especially as the decoration and functionalization of the particle surface for further applications gets more and more into focus. One promising approach for the functionalization exclusively on the particle surface is the use of surfmers (surfactant and monomer). Herein, we present the synthesis of a new family of surfmers and their use for decorating nanoparticles with phosphonate groups through miniemulsion polymerization. Furthermore the synthesis of a dye-labeled functional surfmer provided an elegant manner to evaluate and get deeper insights about its copolymerization. Additionally, potential applications of the synthesized particles in biological studies as well as their use as template for biomimetic mineralization are presented.

New molecules combining the functionalities of surface activity, polymerizability, and fluorescent properties within one molecule that could be seen as a fluorescent surfmer (surfactant and monomer) were successfully synthesized. A long hydrocarbon tail capped with a methacrylamide unit was anchored to a mono- or double-sulfonated Bodipy core. Time-resolved fluorescence measurements in aqueous solutions of the dyes enable one to trace the micelle formation and to find strong polarity dependence of fluorescence properties of the dyes. By using these molecules, polystyrene nanoparticles with fluorescent interfaces were synthesized via miniemulsion polymerization. The surfmers can be used alone or as surfactant additional to sodium dodecyl sulfate that provides stable emulsions and dispersions with a wide range (100–250 nm) of realizable particle sizes after polymerization. All synthesized nanoparticles showed bright fluorescence and can be easily investigated with conventional fluorescent confocal microscopy. Only the fluorescence of particles with double-sulfonated surfmer used is strongly sensitive to fluorescent quenchers as sodium iodide or methyl viologene dissolved in the continuous phase. In contrast, the fluorescence of nanoparticles labeled with the monosulfonated surfmer is only weakly quenched that might be explained by specific orientation of the Bodipy core at particle/water interface.

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