Synthesis, structures and Co-crystallizations of perfluorophenyl substituted β-diketone and triketone compounds

Abstract

Perfluorophenyl-substituted compounds, 3-hydroxy-1,3-bis(pentafluorophenyl)-2-propen-1-one (H1) and 1,5-dihydroxy-1,5-bis(pentafluorophenyl)-1,4-pentadien-3-one (H 2 2), 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 H1 and H 2 2 quantitatively formed co-crystals with the corresponding non-perfluorinated compounds, dibenzoylmethane (H3) and 1,5-dihydroxy-1,5-diphenyl-1,4-pentadien-3-one (H 2 4), respectively, through the arene–perfluoroarene interaction to give the 1:1 co-crystals H1•H3 and H 2 2•H 2 4, which were characterized by X-ray crystallographic and elemental analysis studies.