Two fluorescent 2,6-substituted pyridyl boron-dipyrromethene dyes for selective sensing of cuprous ions

•Two pyridine-substituted BODIPY dyes were prepared via Suzuki coupling reactions;•Two dyes are fluorescent with high quantum yields and little solvent dependence;•Two dyes show highly selective Cu+ sensing properties.

Two new pyridine-substituted boron-dipyrromethene (BODIPY) dyes have been synthesized via the Suzuki coupling reactions of 2,6-diiodo-1,3,5,7-tetramethyl-8-methyl-4,4-difluoroboradiazaindacene and respective pyridinylboronic acid. The molecular structures of the two title compounds have been determined by single-crystal X-ray diffraction analyses. The absorption and steady-state fluorescent properties in different solvents were investigated, which showed that the two compounds are highly fluorescent with a relatively small Stokes shift, high fluorescent quantum yields and little solvent dependence, similar to other BODIPY chromophores. The fluorescence of two compounds were highly sensitive towards Cu+, owing to significant interactions between Cu+ and the nitrogen atoms on the pyridine rings.

Graphical abstractTwo fluorescent pyridine-substituted boron-dipyrromethene (BODIPY) dyes were prepared and shown to be highly selective towards Cu+.Figure optionsDownload full-size imageDownload as PowerPoint slide