Thermally Polymerized Rylene Nanoparticles

Abstract

Rylene dyes functionalized with varying numbers of phenyl trifluorovinyl ether (TFVE) moieties were subjected to a thermal emulsion polymerization to yield shape-persistent, water-soluble chromophore nanoparticles. Perylene and terrylene diimide derivatives containing either two or four phenyl TFVE functional groups were synthesized and subjected to thermal emulsion polymerization in tetraglyme. Dynamic light scattering measurements indicated that particles with sizes ranging from 70 to 100 nm were obtained in tetraglyme, depending on monomer concentration. The photophysical properties of individual monomers were preserved in the nanoemulsions, and emission colors could be tuned between yellow, orange, red, and deep red. The nanoparticles were found to retain their shape upon dissolution into water, and the resulting water suspensions displayed moderate to high fluorescence quantum yield.