Synthesis of fluorescent chalcones, photophysical properties, quantitative structure-activity relationship and their biological application

Abstract

The development of fluorescent pigments is an area of interest in several research fields due to their high sensitivity. In the current study-eight known and three new N,N-dimethylamino-chalcones (12a-k) were synthesized with good yields using the Claisen-Schmidt reaction. For each molecular system, the photophysical properties, including the maximum absorption wavelength (λ_Absorption), molar absorption coefficient (ε), maximum excitation wavelength (λ_Excitation), maximum emission wavelength (λ_Emission), Stokes Shift (Δλ), fluorescence quantum yield (Φ_fl), fluorescence lifetime (τ_fl), radiative and non-radiative rate constants (k_R and k_NR, respectively) were evaluated. Variations in each of these properties were analyzed depending on the substituents present on each compound. To relate the chemical structures of the synthesized compounds to their photophysical properties, Hansch analysis (2D-QSPR) was applied. As a result of Hansch analysis, we found different photophysical properties related to molecular orbitals and the energy of their derivatives (Highest Occupied Molecular Orbital-HOMO, Lowest Unoccupied Molecular Orbital-LUMO, Difference between LUMO-HOMO-ΔLH, Chemical potential-µ, Hardness-η, Softness-S, and electrophilic global index-ω) as well as to the atomic charges on atoms C₅, C_α, C_β, and CO. The application of this type of analysis has made it possible to understand and subsequently design new molecules with defined photophysical properties. Finally, the compounds were use as fluorescent pigment to get living cell imaging on breast cancer cells, obtaining the compound 12a as promissory alternative.

Keywords: Absorption properties; Chalcone; Emission properties; Living cell imaging; Quantitative Structure-Property Relationship.