TY - JOUR
T1 - Synthesis, structures and Co-crystallizations of perfluorophenyl substituted β-diketone and triketone compounds
AU - Kusakawa, Takumi
AU - Sakai, Shunichiro
AU - Nakajima, Kyosuke
AU - Yuge, Hidetaka
AU - Rzeznicka, Izabela I.
AU - Hori, Akiko
N1 - Funding Information:
AAuutthhoorr CCoonnttrriibbuuttiioonnss:: SSyynntthheesseess:: TT..KK..,, SS..SS.. && KK..NN..;; ccaallccuullaattiioonnss,, mmeeaassuurreemmeennttss aanndd oorriiggiinnaall ddrraafftt pprreeppaarraattiioonn:: T.K.; supervision: H.Y. & I.I.R.; manuscript review and editing: I.I.R & A.H.; crystal structure analysis, conceptualization, funding acquisition and project administration: A.H. conceptualization, funding acquisition and project administration: A.H. Funding: This research was funded by Grant-in-Aid for Scientific Research C (No. 18K05153) of JSPS KAKENHI. Funding: This research was funded by Grant-in-Aid for Scientific Research C (no.18K05153) of JSPS KAKENHI. Conflicts of Interest: The authors declare no conflict of interest. Conflicts of Interest: The authors declare no conflict of interest.
Publisher Copyright:
© 2019 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2019/3
Y1 - 2019/3
N2 - 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.
AB - 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.
KW - Co-crystals
KW - Electrostatic interactions
KW - Fluorine
KW - Keto-enol form
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U2 - 10.3390/cryst9030175
DO - 10.3390/cryst9030175
M3 - Article
AN - SCOPUS:85064641017
SN - 2073-4352
VL - 9
JO - Crystals
JF - Crystals
IS - 3
M1 - 175
ER -