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

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.