Cyclic voltammetry of ferrocene-containing β-diketones as a tool to obtain group electronegativities. The structure of 3-ferrocenoyl-1,1,1-trifluoro-2-hydroxyprop-2-ene

Plessis, W.C. du; Erasmus, Johannes J.C.; Lamprecht, G. J.; Conradie, Jeanet; Cameron, T. Stanley; Aquino, Manuel A.S.; Swarts, Jannie C.

doi:10.1139/cjc-77-3-378

Cited by 7 publications

(12 citation statements)

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“…1 In ferrocenyl-containing chalcones, one (or more) of the aromatic rings are replaced with a ferrocenyl group. 2 The catalytic, 3-5 electrochemical 6-10 and structural properties, 6,11,12 of ferrocene and its derivatives, like ferrocenyl-containing chalcones, have been studied with a variety of different techniques. However, characterization by means of X-ray photoelectron Spectroscopy (XPS) is unvisited for these complexes.…”

Section: Introductionmentioning

confidence: 99%

Electronic effects of group fragments on the XPS of Fe 2p and 3p photoelectron lines of ferrocenyl-containing chalcones

Erasmus

2017

S.Afr.j.chem.

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A series of ferrocenyl-containing chalcones, Fc-CO-CH=CH-C 6 H 4 R, with the R-group on the para-position on the phenyl ring and R = OCH 3 (1), CH 3 (2), C 6 H 5 (3), tBu (4), H (5), Br (6) and CF 3 (7) were subjected to an X-ray photoelectron spectroscopy (XPS) study. The linear relationships obtained between the Gordy-scale group electronegativity of molecular fragment R, ÷ R , and the maximum binding energies of the Fe 2p 3/2 and the Fe 3p 3/2 photoelectron lines, confirmed communication between the iron atom of the ferrocene moiety and the molecular fragments, R, of 1-7. These relationships illustrated that the influence of the electronic properties of the molecular fragments are more pronounced in the Fe 3p photoelectron lines than in the Fe 2p photoelectron lines.

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Section: Introductionmentioning

confidence: 99%

Electronic effects of group fragments on the XPS of Fe 2p and 3p photoelectron lines of ferrocenyl-containing chalcones

Erasmus

2017

S.Afr.j.chem.

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“…Initially, we investigated the unique redox behavior of 1,3-ferrocenyl-2-buten-1-one (DFcB) [8], which has two nonequivalent redox centers. Two pairs of well-defined and nearly symmetric redox peaks in the CV, which are corresponding to two consecutive electron transfer steps [8,9]. In our recent studies of 1,3,5-triferrocenylbenzene, it has been confirmed that strong intramolecular electronic communications exist among the three ferrocene centers [10,11].…”

Section: Introductionmentioning

confidence: 82%

“…The thin-film approach has been proven to be powerful in studying the redox properties of hydrophobic compounds [4][5][6][7][8][9][10], for which the conventional electrochemical method (i.e., carrying out electrochemical measurements in bulk electrolyte) has its challenges. The low solubility of these molecules makes it difficult to obtain strong signals in aqueous electrolyte; when an organic solvent was used, the signal may be distorted by the high solvent resistance.…”

Section: Introductionmentioning

confidence: 99%

“…While the redox behavior of multi-center ferrocenyl derivatives was systematically investigated [8][9][10][11][12][13], it is interesting to expand such studies with the investigation of their heterocyclic counterparts. In addition, the recent development of new and efficient coupling methods involving heterocycles such as pyridines and pyrimidines have rendered the access to a new class of ferrocene coupled pyrimidines possible; nonetheless, their electrochemical and spectroscopic properties have not yet been well characterized [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

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Unique Intramolecular Electronic Communications in Mono-ferrocenylpyrimidine Derivatives: Correlation between Redox Properties and Structural Nature

Xiang

Noel

Shao

et al. 2015

Electrochimica Acta

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“…The two observed waves for compounds 1, 3, 4 and 6 are associated with the typical symmetrical dimers which produce a mixed valent transition upon reduction or oxidation. Reductions Table 2 Selected bond lengths (Å) and angles ( ) for compounds 4 and 5. potentials on the side groups of symmetrical complexes that generate mixed valent intermediates have been reported [49]. These systems either allow electron delocalization from direct metal-metal interaction or through the bridge path.…”

Section: Electrochemical Studiesmentioning

confidence: 99%

Synthesis, crystal structures and electrochemical properties of ferrocenyl imidazole derivatives

Labulo

Omondi

Nyamori

2019

Heliyon

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Six ferrocenyl imidazole derivatives substituted with -Cl, -NO2 and -CH3 on the 2-position of the 1H-imidazole ring have been synthesized. Of the six compounds, the di-substituted ferrocenes, i.e. compounds 4 (1,1′-ferrocenylmethyl(2-chloroimidazole)), 5 (1,1′-ferrocenyl(2-nitroimidazole)), and 6 (1,1′-ferrocenylmethyl(2-methylimidazole)) are reported for the first time. The structure-property relationships of compounds 4, 5 and 6 were investigated by means of UV-visible, FTIR, 1H-NMR, 13C-NMR spectroscopy and electrochemical studies. UV-visible analysis in acetonitrile showed that the π -π* band of compounds 2 (1-ferrocenylmethyl(2-nitroimidazole)) and 5 appeared at longer wavelength compared to 1 (1-ferrocenylmethyl(2-chloroimidazole)), 3 (1-ferrocenylmethyl(2-methylimidazole)), 4 and 6. This phenomenon is due to the different electronics around the imidazole moieties. In cyclic voltammetry analysis, all compounds exhibited a quasi-reversible redox wave for the ferrocenyl and imidazole moieties. Density functional theoretical (DFT) calculations with the B3LYP/6-311+G(d) basis set were performed on compounds 1–6, and the calculated HUMO-LUMO band gap energies correlated with those obtained from electrochemical and spectroscopic data. The X-ray crystallographic analysis highlighted the effect of electron-withdrawing and electron-donating substituents on the conformation of the cyclopentadienyl rings attached to the ferrocenyl moiety.

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Cyclic voltammetry of ferrocene-containing β-diketones as a tool to obtain group electronegativities. The structure of 3-ferrocenoyl-1,1,1-trifluoro-2-hydroxyprop-2-ene

Cited by 7 publications

References 0 publications

Electronic effects of group fragments on the XPS of Fe 2p and 3p photoelectron lines of ferrocenyl-containing chalcones

Electronic effects of group fragments on the XPS of Fe 2p and 3p photoelectron lines of ferrocenyl-containing chalcones

Unique Intramolecular Electronic Communications in Mono-ferrocenylpyrimidine Derivatives: Correlation between Redox Properties and Structural Nature

Synthesis, crystal structures and electrochemical properties of ferrocenyl imidazole derivatives

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