Synthesis, structure, and some properties of 1-phenyl-3-methyl-4-(2,3,4,5,6-pentafluorobenzoyl)pyrazol-5-one and its lanthanide complexes

Synthesis, structure, and some properties of... A new 4-acylpyrazolone—1-phenyl-3-methyl-4-(2,3,4,5,6-pentafluorobenzoyl)-1H-pyrazole-5(4H)-one (Pfb-PMPH)—was prepared in a high yield by the reaction of 1-phenyl-3-methylpyrazol-5-one with pentafluorobenzoyl chloride in the presence of calcium and barium hydroxides. On heating this compound in vacuum up to 170°C, elimination of HF takes place to give the intramolecular cyclization product, 1-phenyl-3-methyl-5,6,7,8-tetrafluorochromeno[2,3-c]pyrazol-4(1H)-one. The structures of Pfb-PMPH (HL1) and the cyclization product (L2) were determined by X-ray diffraction (CIF files CCDC nos. 1010331 (HL1), 1010332 (L2), 1010333 (VI), 1010334 (VII), 1010335 (VIII), 1010336 (IX), and 1010337 (X)). The reactions of Pfb-PMPH with lanthanide silylamides [(Me3Si)2N]3Ln in a THF solution give pyrazolonate complexes (Pfb-PMP)3Ln(THF) (Ln = Sm, Eu, Gd, Tb, Lu). The compounds react with Ph3PO to give the derivatives (Pfb-PMP)3Ln(OPPh3)2 · xEtOH, which were studied by X-ray diffraction. The synthesized lanthanide complexes are luminescent at room temperature and exhibit ligand- and metal-centered emission. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Journal of Coordination Chemistry Springer Journals

Synthesis, structure, and some properties of 1-phenyl-3-methyl-4-(2,3,4,5,6-pentafluorobenzoyl)pyrazol-5-one and its lanthanide complexes

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Publisher
Springer Journals
Copyright
Copyright © 2015 by Pleiades Publishing, Ltd.
Subject
Chemistry; Physical Chemistry; Inorganic Chemistry
ISSN
1070-3284
eISSN
1608-3318
D.O.I.
10.1134/S1070328415010091
Publisher site
See Article on Publisher Site

Abstract

A new 4-acylpyrazolone—1-phenyl-3-methyl-4-(2,3,4,5,6-pentafluorobenzoyl)-1H-pyrazole-5(4H)-one (Pfb-PMPH)—was prepared in a high yield by the reaction of 1-phenyl-3-methylpyrazol-5-one with pentafluorobenzoyl chloride in the presence of calcium and barium hydroxides. On heating this compound in vacuum up to 170°C, elimination of HF takes place to give the intramolecular cyclization product, 1-phenyl-3-methyl-5,6,7,8-tetrafluorochromeno[2,3-c]pyrazol-4(1H)-one. The structures of Pfb-PMPH (HL1) and the cyclization product (L2) were determined by X-ray diffraction (CIF files CCDC nos. 1010331 (HL1), 1010332 (L2), 1010333 (VI), 1010334 (VII), 1010335 (VIII), 1010336 (IX), and 1010337 (X)). The reactions of Pfb-PMPH with lanthanide silylamides [(Me3Si)2N]3Ln in a THF solution give pyrazolonate complexes (Pfb-PMP)3Ln(THF) (Ln = Sm, Eu, Gd, Tb, Lu). The compounds react with Ph3PO to give the derivatives (Pfb-PMP)3Ln(OPPh3)2 · xEtOH, which were studied by X-ray diffraction. The synthesized lanthanide complexes are luminescent at room temperature and exhibit ligand- and metal-centered emission.

Journal

Russian Journal of Coordination ChemistrySpringer Journals

Published: Feb 13, 2015

References

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