Blue emitting side-chain pendant 4-hydroxy-1,3-thiazoles in polystyrenes synthesized by RAFT polymerization

Blue emitting dyes bearing a luciferin analogous chromophore were attached to a polystyrene backbone. For this purpose, 4-hydroxy-1,3-thiazoles were functionalized with a styrene unit and polymerized using the reversible addition–fragmentation chain transfer (RAFT) polymerization technique. Two different chain transfer agents were investigated and one monomer was studied in terms of its kinetic behavior. The polymerization kinetics are presented and discussed in detail, showing a controlled polymerization behavior, resulting in well-defined copolymers with polydispersity indices below 1.2. The obtained polymers were characterized by size exclusion chromatography (SEC), 1H NMR, MALDI-TOF MS and UV–vis absorption and fluorescence spectroscopy. In addition, the UV–vis absorption and emission behavior was investigated in thin films.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 4-Hydroxy-1,3-thiazoles were equipped with a polymerizable styrene functionality. ► These dye-labeled monomers were polymerized by the RAFT polymerization technique. ► The polymerization behavior was investigated by a kinetic study. ► The optical properties of the blue emitting monomers and polymers were compared.