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 (H22), 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 H22 quantitatively formed co-crystals with the corresponding non-perfluorinated compounds, dibenzoylmethane (H3) and 1,5-dihydroxy-1,5-diphenyl-1,4-pentadien-3-one (H24), respectively, through the arene–perfluoroarene interaction to give the 1:1 co-crystals H1•H3 and H22•H24, which were characterized by X-ray crystallographic and elemental analysis studies.
Highlights
Fluorine-substituted organic molecules are being widely explored by materials scientists in various applications encompassing battery, catalysis, and many other technological fields [1,2,3,4,5].Ring fluorination dramatically changes molecular characteristics through intramolecular electron withdrawing nature and intermolecular electrostatic interactions
The corresponding ligand, 3-hydroxy-1,3-bis(pentafluorophenyl)-2propen-1-one (H1) (Scheme 1) [36], which is a unique target for the fluorine-substituted dibenzoylmethane [37], has never been characterized by crystallographic studies, whereas the corresponding coordination complexes have been reported
Single crystals of H1 and H2 2 were obtained from ethanol as colorless and pale yellow prismatic crystals, respectively, which were suitable for X-ray crystallographic studies
Summary
Fluorine-substituted organic molecules are being widely explored by materials scientists in various applications encompassing battery, catalysis, and many other technological fields [1,2,3,4,5]. The co-crystals have alternating layered structures and are found to possess unique molecular recognition capabilities [10]. The corresponding ligand, 3-hydroxy-1,3-bis(pentafluorophenyl)-2propen-1-one (H1) (Scheme 1) [36], which is a unique target for the fluorine-substituted dibenzoylmethane [37], has never been characterized by crystallographic studies, whereas the corresponding coordination complexes have been reported. We investigated the molecular structures and the supramolecular associations of solid states, which further co-crystallize withwith the associations of H1.
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