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Crystals 2019, 9(3), 175;

Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds

Graduate School of Engineering and Science, Shibaura Institute of Technology, Fukasaku 307, Minuma-ku, Saitama 337-8570, Japan
Department of Chemistry, School of Science, Kitasato University, Kitasato 1-15-1, Minami-ku, Sagamihara 252-0373, Japan
Author to whom correspondence should be addressed.
Received: 26 February 2019 / Revised: 15 March 2019 / Accepted: 21 March 2019 / Published: 25 March 2019
(This article belongs to the Special Issue Halogen-Bonded Cocrystals)
PDF [3394 KB, uploaded 25 March 2019]


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. View Full-Text
Keywords: co-crystals; electrostatic interactions; fluorine; keto-enol form co-crystals; electrostatic interactions; fluorine; keto-enol form

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kusakawa, T.; Sakai, S.; Nakajima, K.; Yuge, H.; Rzeznicka, I.I.; Hori, A. Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds. Crystals 2019, 9, 175.

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