Chemical and electrochemical oxidation studies on new copper(I) ferrocenyl-functionalised β-diketonates

Jakob, Alexander; Joubert, Chris C.; Rüffer, Tobias; Swarts, Jannie C.; Lang, Heinrich

doi:10.1016/j.ica.2013.11.019

Cited by 9 publications

(15 citation statements)

References 77 publications

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“…4 as a representative example. The cyclic voltammograms of the complexes display three oxidative responses in the potential range 0.0-0.8 V. The anodic wave observed at 0.22 V, with the corresponding cathodic wave at 0.02 V, is attributed to the Cu I/II couple, which is in agreement with similar reports on Cu(I) complexes[47][48][49][50]. The two quasi-reversible anodic processes observed at 0.62 and 0.73 V are due to the oxidation of the benzene rings of triphenylphosphine and the Br -anion[48,50].…”

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confidence: 90%

Synthesis, characterization and X-ray crystal structure of copper(I) complexes of the 2-(2-quinolyl)benzothiazole ligand. Electrochemical and antibacterial studies

et al. 2015

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confidence: 90%

Synthesis, characterization and X-ray crystal structure of copper(I) complexes of the 2-(2-quinolyl)benzothiazole ligand. Electrochemical and antibacterial studies

et al. 2015

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“…1 and 2, while selected bond lengths and angles are listed in Table 3. Compound 1 crystallizes in the monoclinic system with space group P2 1 /c, while complex [19,20,24,48,49]. By contrast, the binuclear unit of 2 exhibits two pentacoordinated Cu(II) centers in a square pyramidal (4+1) coordination geometry (Fig.…”

Section: Description Of the Molecular And Crystal Structuresmentioning

confidence: 99%

Doubly phenoxide-bridged binuclear copper(II) complexes with ono tridentate schiff base ligand: Synthesis, structural, magnetic and theoretical studies

et al. 2015

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International audienceThe tridentate ONO-donor Schiff base ligand H2L, derived from the condensation of 1-anisyl-1,3-butanedione and 2-aminophenol, was generated in situ and reacted with Cu(NO3)2*3H2O to yield two doubly phenoxo bridged di-copper(II) complexes depending on the nitrogenous base used. [Cu2L2] (1) is obtained in 85% and 75% yield in the presence of pyridine or 4-picoline, respectively, and [(py-tBu)2Cu2L2] (2) is isolated in 75% yield in the presence of 4-tert-butylpyridine. Compounds 1 and 2 were characterized in the solid-state by elemental analysis and FT-IR spectroscopy. Single crystal X-ray diffraction study reveals that in 1 the two four-coordinated copper atoms adopt a square planar geometry, whereas in 2 each Cu(II) metal ion shows a five coordinate square pyramidal (ONO,N + O) geometry. In each dimer, two μ-phenolic oxygen atoms bridge the two half-units forming a planar Cu2O2 core. EPR studies in fluid solutions indicate that the dimeric structure of 1 and 2 is destroyed upon dissolution. In the solid-state, 1 is EPR silent, whereas 2 presents an unresolved broad resonance (ΔH peak-to-peak = 71.5 G) with g = 2.071 at 298 K, along with the triplet state (S = 1) signature at g = 4.181. Variable temperature (2-300 K) magnetic susceptibility measurements exhibit strong antiferromagnetic interactions between the Cu(II) centers with a J value of −397 cm−1 for 1, while no interaction operates between the two spins localized on Cu(II) metal ions in 2. Ab initio calculations were also performed to supplement the experimental results

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“…The IR spectra are characterized by the appearance of CO vibrations typical for β-diketones ( 5 – 7 , 9 ) or metal β-diketonates ( 10 – 12 ) in the range of 1500–1680 cm −1 [ 39 , 40 , 102 , 103 ]. For the respective diferrocenyl pyrazoles 13 – 15 , representative vibrations could be observed for the N-H (3392 cm −1 ), N-C (ca.…”

Section: Resultsmentioning

confidence: 99%

“…200 ppm. For the ferrocenyl groups, in total, four signals are observed between 65–80 ppm, which is typical for the C 5 H 4 and C 5 H 5 perimeters ( Section 4 ) [ 36 , 37 , 38 , 39 , 40 , 41 ].…”

Section: Resultsmentioning

confidence: 99%

“…In addition, they received great interest in the synthesis of (hetero)multimetallic complexes [ 23 , 24 , 25 , 26 , 27 , 28 , 29 ] as catalysts in organic synthesis [ 30 , 31 , 32 ] and as anticancer drugs (especially copper and rhodium β-diketonates) [ 33 , 34 , 35 ]. Recently, they gained topical attention in the study of electron transfer processes, when, for example, redox-active groups such as ferrocenyls are present, i.e., in zirconium, hafnium, copper(I), copper(II), manganese, ruthenium, rhodium(I), and aluminum β-diketonate complexes [ 36 , 37 , 38 , 39 , 40 , 41 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Electrochemistry of Diferrocenyl β-Diketones, -Diketonates, and Pyrazoles

Lehrich

Mahrholdt²,

Korb³

et al. 2020

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The synthesis of FcC(O)CH(R)C(O)Fc (Fc = Fe(η5-C5H4)(η5-C5H5); R = H, 5; nBu, 7; CH2CH2(OCH2CH2)2OMe, 9), [M(κ2O,O′-FcC(O)CHC(O)Fc)n] (M = Ti, n = 3, 10; M = Fe, n = 3, 11; M = BF2, n = 1, 12), and 1-R’-3,5-Fc2-cC3HN2 (R’ = H, 13; Me, 14; Ph, 15) is discussed. The solid-state structures of 5, 7, 9, 12, 13, 15, and 16 ([TiCl2(κ2O,O′-PhC(O)CHC(O)Ph)2]) show that 7 and 9 exist in their β-diketo form. Compound 13 crystallizes as a tetramer based on a hydrogen bond pattern, including one central water molecule. The electrochemical behavior of 5–7 and 9–16 was studied by cyclic and square-wave voltammetry, showing that the ferrocenyls can separately be oxidized reversibly between −50 and 750 mV (5–7, 9, 12–15: two Fc-related events; 10, 11: six events, being partially superimposed). For complex 10, Ti-centered reversible redox processes appear at −985 (TiII/TiIII) and −520 mV (TiIII/TiIV). Spectro-electrochemical UV-Vis/NIR measurements were carried out on 5, 6, and 12, whereby only 12 showed an IVCT (intervalence charge-transfer) band of considerable strength (νmax = 6250 cm−1, Δν½ = 4725 cm−1, εmax = 240 L·mol−1·cm−1), due to the rigid C3O2B cycle, enlarging the coupling strength between the Fc groups.

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Chemical and electrochemical oxidation studies on new copper(I) ferrocenyl-functionalised β-diketonates

Cited by 9 publications

References 77 publications

Synthesis, characterization and X-ray crystal structure of copper(I) complexes of the 2-(2-quinolyl)benzothiazole ligand. Electrochemical and antibacterial studies

Synthesis, characterization and X-ray crystal structure of copper(I) complexes of the 2-(2-quinolyl)benzothiazole ligand. Electrochemical and antibacterial studies

Doubly phenoxide-bridged binuclear copper(II) complexes with ono tridentate schiff base ligand: Synthesis, structural, magnetic and theoretical studies

Synthesis, Characterization, and Electrochemistry of Diferrocenyl β-Diketones, -Diketonates, and Pyrazoles

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