Syntheses, experimental and theoretical studies on absorption/emission properties of pyrazoline-containing aryl/methoxy naphthyl substituents

5-Aryl-3-(2-methoxynaphthalen-6-yl)-1-phenylpyrazoline derivatives were synthesized starting from (E)-1-(3-aryl)-(2-methoxynaphthalen-6-yl)-prop-2-en-1-one and phenylhydrazine. The compounds were characterized by ¹ H and ¹³C nuclear magnetic resonance (NMR), elemental analyses and mass spectrometry. Some compounds showed promising luminescence properties in solution and in solid state; the absorption and emission characteristics were measured and the fluorescence quantum yield of two of the derivatives [4,5-dihydro-3-(2-methoxynaphthalen6-yl)-5-(3,4,5-trimethoxyphenyl)-1- phenyl-1H-pyrazoline and 5-(4-chlorophenyl)-4,5-dihydro3-(2-methoxynaphthalen-6-yl)-1-phenyl-1H- pyrazoline] were found to have excellent values compared to rhodamine B standard. Theoretical calculations at time-dependent density functional theory (TD-DFT) level are in agreement with the experimental measurements and are helpful to explain the electronic behavior. (author)