Synthesis and Spectral Properties of 4‐(2,5‐Dimethoxyphenylmethelene)‐2‐phenyl‐5‐oxazolone (DMPO)

Abstract An interesting flourophore, 4‐(2,5‐dimethoxyphenylmethelene)‐2‐phenyl‐5‐oxazolone (DMPO) was synthesized by mixing an equivalent molar quantity of hippuric acid and 2,5‐dimethoxybenzaldehyde in acetic anhydride in the presence of anhydrous sodium acetate. The absorption and fluorescence characteristics of 4‐(2,5‐dimethoxy‐phenylmethelene)‐2‐phenyl‐5‐oxazolone (DMPO) were investigated in different solvents. DMPO dye exhibits red shift in both absorption and emission spectra as solvent polarity increases, indicating change in the dipole moment of molecules upon excitation due to an intramolecular charge transfer interaction. The fluorescence quantum yield depends strongly on the properties of the solvents, which was attributed to positive and negative solvatokinetic effects. A crystalline solid of DMPO gave strong excimer like emission at 630 nm due to the excitation of molecular aggregates. This is expected from the idealized crystal structure of the dye that belongs to the B‐type class of Steven's Classification. DMPO displayed fluorescence quenching by triethylamine via nonemissive exciplex formation.