A white light emitting single halochromic hydrazine bridged bis(3-pyrrolyl BODIPY) fluorophore

Abstract

In search of white light emitting fluorophores, a hydrazine bridged Schiff base compound, bis(3-pyrrolyl BODIPY), was synthesized by condensing readily available α-formyl 3-pyrrolyl BODIPY with hydrazine hydrate in CH₃OH under reflux for 5 h followed by recrystallization. Bis(3-pyrrolyl BODIPY) was thoroughly characterized by HR-MS, 1D and 2D NMR, and X-ray crystallography. The X-ray structure revealed that the 3-pyrrolyl BODIPY units in the dyad were arranged trans to each other with respect to the hydrazine moiety. Bis(3-pyrrolyl BODIPY) showed absorption bands in the region of 390–705 nm and exhibited multiple fluorescence bands in the region of 395–720 nm at different excitation wavelengths. The protonated derivative of bis(3-pyrrolyl BODIPY) generated by the addition of TFA to its CH₂Cl₂ solution showed significant changes in the optical properties and generated white fluorescence under UV light with specific emission bands observed in blue, green, and red regions, indicating that bis(3-pyrrolyl)BODIPY is a single white light emitting halochromic fluorophore under acidic conditions. DFT and TD-DFT studies justify the structural and electronic properties of the protonated derivative of bis(3-pyrrolyl BODIPY) exhibiting white light emission.