| Summary: | Perfluorophenyl-substituted compounds, 3-hydroxy-1,3-bis(pentafluorophenyl)-2- propen-1-one (H<b>1</b>) and 1,5-dihydroxy-1,5-bis(pentafluorophenyl)-1,4-pentadien-3-one (H<sub>2</sub><b>2</b>), were prepared in 56 and 30% yields, respectively, and only the enol forms were preferentially obtained among the keto-enol tautomerism. Molecular conformations and tautomerism of the fluorine-substituted compounds were certified based on X-ray crystallographic studies and density functional calculations. The solvent dependency of the absorption spectra was only observed for the fluorinated compounds. The compounds H<b>1</b> and H<sub>2</sub><b>2</b> quantitatively formed co-crystals with the corresponding non-perfluorinated compounds, dibenzoylmethane (H<b>3</b>) and 1,5-dihydroxy-1,5-diphenyl-1,4-pentadien-3-one (H<sub>2</sub><b>4</b>), respectively, through the arene–perfluoroarene interaction to give the 1:1 co-crystals H<b>1</b>•H<b>3</b> and H<sub>2</sub><b>2</b>•H<sub>2</sub><b>4</b>, which were characterized by X-ray crystallographic and elemental analysis studies.
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