Electronic Spectroscopies Combined with Quantum Chemistry Calculations: Study of the Interactions of 3-Hydroxyflavone with Copper Ions

The current study aims at obtaining a better understanding of the mechanisms involved in the complexation of copper ions by 3-hydroxyflavone (3HF), which is one of the most studied compounds of the flavonoid family. To achieve this goal, quantum chemistry calculations combined with electronic spectroscopies, including absorption, fluorescence emission, and excitation, have been used. The formation of successive complexes of stoichiometry (metal/ligand) 1:2, 1:1, and 3:2 has been highlighted. Even under acidic conditions (pH = 4.0), the a-hydroxy-keto function of the molecule presents a high complexing power with regard to copper ions, insofar as a stable complex of 1:2 stoichiometry is obtained with a large conditional stability constant (log beta = 8.7). The formation of this predominant species induces a quenching of the dual fluorescence of 3HF, whereas the second complex of stoichiometry 1:1 presents a fluorescence emission.