Meso-pyrrolyl BODIPY based colorimetric optical sensor for Cu2+ ions

Abstract

A simple meso-pyrrolyl BODIPY-Schiff base conjugate was synthesized by reacting ([Formula: see text]-formylpyrrolyl) BODIPY with 2-aminophenol in ethanol at reflux followed by recrystallization from CH2Cl2/petroleum ether, affording the conjugate in 72% yield. The conjugate was thoroughly characterized by HR-MS, 1D and 2D NMR and X-ray crystallographic techniques. The X-ray structure of the meso-pyrrolyl BODIPY-Schiff base conjugate revealed that the meso-pyrrole and the phenyl substituents were deviated by an angle of 35° and 49°, respectively, from the plane of the BF2-dipyrrin core. The absorption spectrum of the conjugate was similar to the ([Formula: see text]-formylpyrrolyl) BODIPY with a strong absorption band at 508 nm, whereas the fluorescence of the ([Formula: see text]-formylpyrrolyl) BODIPY was completely quenched in the BODIPY-Schiff base conjugate. Furthermore, cation sensing studies revealed that the conjugate has a specific sensing ability for the Cu(II) ion even in the presence of the other metal ions, as verified by the visual, absorption and mass spectral studies. The DFT optimized structure revealed that the Cu(II) ion was bound to pyrrolic nitrogen, imine nitrogen, phenolic oxygen and two water molecules in a distorted square pyramidal fashion. TD-DFT studies accounted well for the absorption spectra of the BODIPY-Schiff base conjugate and its Cu[Formula: see text] bound complex.