Investigation of interactional behavior and relative photo-physical properties in a group of bioactive compounds

[Display omitted] •Solvation interactions and dipole moments a group of chacone drugs are evaluated by experimental and theoretical methods.•Specific and non–specific interactions play a key role in spectral properties of chalcone drug.•Intra–molecular charge transfer during the excitation process takes place in chalcone drugs.•Experimental SAS control dipole moment of chalcone drugs.•The obtained effective molecular interactions and dipole moments show applicability of chalcone drugs in biological systems. In recent years, numerous researchers have faced the challenge of synthesizing bioactive compounds. Hence, chalcones with bioactive anti–cancer characteristics have attracted interests in many pharmaceutical studies. In this work, we focused on photo–physical behavior of three chalcones, with similar structures, in various solvent media, in order to study and compare their similarities and differences. Theoretical techniques were used to validate the experimental results. The experimental and theoretical results help to expand and better the realization of the photo–physical characteristics of these compounds and reveal essential information about the activity of this group of compounds in biological systems. The results show that photo–physical behavior of the chalcones is related to the solvent–solute interactions. Linear solvation energy relationship (LSER) model of Kamlet–Abboud–Taft and Catalán were used to analyze the interactions of chalcones in various media. The ground and excited state dipole moments of these bioactive compounds were obtained using Lippert’s, Bakshiev’s and Ghamma–Viallet’s solvatochromic shift methods and their molecular resonance forms were presented. Finally, these results were compared and discussed by time–dependent density functional theory and configuration interaction calculations.