Four different bright yellow to orange hydroxy-substituted chalcones (i.e., 2',4-di-hydroxy (1), 2',3',4-trihydroxy (2), 2',3',4'-trihydroxy (3), and 2'-hydroxy-4-methoxy (4) chalcones) were synthesized and characterized by LC-MS, FT-IR, FT-Raman, and fluorescence spectroscopy and thermogravimetric analysis. UV-visible absorption spectroscopy was also used. The experimental (theoretical) bandgaps of 1, 2, 3, and 4 are 2.89 (2.90), 2.93 (2.95), 3.04 (3.09), and 3.01 (2.91) eV, respectively. The hydroxy-substituted chalcones exhibited strong dual emissions as a consequence of the locally excited states followed by internal charge transfer processes. The molecular structures, lowest energy transitions, vibrational frequencies, and spectroscopic information were calculated using density functional theory and time-dependent density functional theory methods at the B3LYP/6-31G(d,p) theoretical level. The experimental and theoretical data were compared and the relationship between them was briefly discussed.
Keywords: DFT calculations; HOMO–LUMO; Hydroxy-substituted chalcones; Vibrational spectra.
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