BODIPY chromophores as efficient green light sensitizers for lanthanide-induced near-infrared emission

Abstract

A new boron dipyrromethene (BODIPY) modified 8-hydroxylquinoline ligand (8-HOQ-BODIPY) is synthesized for the sensitization of near-infrared emission of lanthanide(III) ions. The BODIPY unit, as revealed by single-crystal X-ray diffraction analysis, aligns almost perpendicularly to the 8-HOQ unit. The ligand exhibits strong absorption at ∼506 nm and fluorescence at 510 nm in organic solvents with quantum yields ranging from ∼0.45 in dichloromethane to 0.015 in ethanol. It forms stable ytterbium(III), erbium(III) and neodymium(III) complexes with 3 : 1 ligand-to-metal molar ratios. Upon excitation (∼522 nm), the neodymium(III) and erbium(III) complexes emit weakly at 1060 and 1382 nm, respectively, whereas the ytterbium(III) complex exhibits strong emission at 976 and 1003 nm. The results demonstrate the potential of BODIPY dyes as efficient and robust visible light sensitizers for lanthanide-based NIR emitters in medical diagnosis.