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In this work, the photosensitizing properties of ferrocene (Fc)-based compounds FcCH2CS3CH2Fc (1) and FcCH 2SSCH2Fc (2) were investigated and significant enhancement in the light harvesting efficiency was observed compared to those achieved with previously reported compounds from our lab. The compounds were fully characterized by spectroscopy and X-ray crystallography, and their electrochemical properties studied. DSSCs based on these dyes display efficiencies comparable to those of a standard cell based on N719 under similar experimental conditions. These studies demonstrate that ferrocenyl-based sulfur rich compounds with proper orientation of the Fc groups assisted via suitable linkers, together with desired redox properties and visible region electronic absorption features could constitute a new class of photosensitizers targeting light driven reactions.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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The phosphorus-chiral diphosphine 1,1?-bis(1-naphthylphenylphosphino)ferrocene (1a) and its new electronically modified derivatives 1b-d bearing methoxy and/or trifluoromethyl groups in para positions of the phenyl rings were investigated as ligands in rhodium-catalyzed (asymmetric) hydroformylation. Depending on ligand basicity, high-pressure NMR and IR characterization of the respective (diphosphine) rhodium dicarbonyl hydride precursor complexes revealed subtle differences in the occupation of bis-equatorial (ee) and equatorialapical (ea) coordination geometries. The high ee:ea ratio of the four complexes contrasted with the clear ea preference observed for the related achiral compound dppf (1,1?-bis-(diphenylphosphino)ferrocene). In the hydroformylation of styrene the best result (50% ee) was obtained by employing the best pi-acceptor ligand 1c, incorporating two p-trifluoromethyl substituents. Substrate electronic variations using 4-methoxystyrene and 4-chlorostyrene showed a pronounced influence on turnover frequencies, branched/linear aldehyde product ratios, and enantiodiscrimation, whereas in the hydroformylation of 1-octene ligand electronic perturbations did affect only the rate, but not the selectivity of the reaction.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Acylferrocenes reacted with samarium diiodide in the presence of water to give the corresponding (alpha-hydroxyalkyl)ferrocenes or alkylferrocenes depending on the reaction time and temperature. On treatment with samarium diiodide in the absence of water, ferrocenecarbaldehyde underwent a reductive coupling to give pinacols, whereas acetylferrocene yielded 3,3-diferrocenyl-2-butanone and 2,3-diferrocenyl-2-butene via the subsequent rearrangement and deoxygenation.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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We propose an analytical method based on electrochemical collisions to detect individual graphene oxide (GO) sheets in an aqueous suspension. The collision rate is found to exhibit a complex dependence on redox mediator and supporting electrolyte concentrations. The analysis of multiple collision events in conjunction with numerical simulations allows quantitative information to be extracted, such as the molar concentration of GO sheets in suspension and an estimate of the size of individual sheets. We also evidence by numerical simulation the existence of edge effects on a 2D blocking object.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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A number of 1,1?-bis(benzo-1,3-dithiol-2-ylidene)ferrocene derivatives 7a-b and 12-14 based on the strong electron donating ability of 1,3-dithiole and ferrocene moieties were synthesized as new pi-donors. The structure and physical properties of these compounds were characterized both by experimental techniques and spectral analysis. These new classes of donor compounds were obtained in very high yields based on modification of the Wittig-Horner reaction and the 1,3-dithiole rings were separated by conjugated spacers including aryl-ferrocenyl- aryl. The electrochemical properties of the new compounds have been studied in comparison to DB-TTF 4 analogues, and the parent ferrocene donor by cyclic voltammetry (CV), using Pt electrode as the working electrode in CH2Cl2 solutions at room temperature. Three subsequent oxidation processes are observed as three oxidation waves associated only with two reduction processes. Polycrystalline samples of 14a-b are conducting sigma rt 14a=0.2 S cm-1 and sigma rt 14b=4.8×10-4 S cm-1) respectively, while compounds 15 and 16 were found essentially as insulator (sigma rt<10-10 S cm-1). We very much hope you enjoy reading the articles and that you will join us to present your own research about 1273-94-5, you can contact me at any time and look forward to more communication. Recommanded Product: 1273-94-5

Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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A new series of donor-bridge-acceptor (D-B-A) compounds consisting of pi-conjugated oligofluorene (oFL) bridges between a ferrocene (Fc) electron-donor and a fullerene (C60) electron-acceptor have been synthesized. In addition to varying the length of the bridge (i.e., mono- and bi-fluorene derivatives), four different ways of linking ferrocene to the bridge have been examined. The Fc moiety is linked to oFL: 1) directly without any spacer, 2) by an ethynyl linkage, 3) by a vinylene linkage, and 4) by a p-phenylene unit. The electronic interactions between the electroactive species have been characterized by cyclic voltammetry, absorption, fluorescence, and transient absorption spectroscopy in combination with quantum chemical calculations. The calculations reveal exceptionally close energy-matching between the Fc and the oFL units, which results in strong electronic-coupling. Hence, intramolecular charge-transfer may easily occur upon exciting either the oFLs or Fcs. Photoexcitation of Fc-oFL-C60 conjugates results in transient radical-ion-pair states. The mode of linkage of the Fc and FL bridge has a profound effect on the photophysical properties. Whereas intramolecular charge-separation is found to occur rather independently of the distance, the linker between Fc and oFL acts (at least in oFL) as a bottleneck and significantly impacts the intramolecular charge-separation rates, resulting in beta values between betaCS 0.08 and 0.19 A-1. In contrast, charge recombination depends strongly on the electron-donor-acceptor distance, but not at all on the linker. A value of betaCR (0.35±0.01 A-1) was found for all the systems studied. Oligofluorenes prove, therefore, to be excellent bridges for probing how small structural variations affect charge transport in D-B-A systems. Finely tuned transfer: Chemical modification of the oligo-fluorene linkers between Fc and C60 units enables fine-tuning of photoinduced charge-transfer processes in new donor-bridge-acceptor conjugates (see illustration). Copyright

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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The super electrophilicity of a shelf-stable, easily prepared trifluoromethylthiolating reagent N-trifluoromethylthio-dibenzenesulfonimide 7 was demonstrated. Consistent with the theoretical prediction, 7 exhibits reactivity remarkably higher than that of other known electrophilic trifluoromethylthiolating reagents. In the absence of any additive, 7 reacted with a wide range of electron-rich arenes and activated heteroarenes under mild conditions. Likewise, reactions of 7 with styrene derivatives can be fine-tuned by simply changing the reaction solvents to generate trifluoromethylthiolated styrenes or oxo-trifluoromethylthio or amino-trifluoromethylthio difunctionalized compounds in high yields.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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New open-chain tetraamines containing ferrocene, 1,1?-bis(5-methyl-2,5-diazahexyl)ferrocene L1 and 1,1?-bis(2,5-diazahexyl)ferrocene L2, have been synthesized and characterized. Their protonation behaviour has been studied by potentiometric titrations in water (0.1 mol dm-3 KNO3, 25C). The co-ordination ability of L1 towards the divalent metal ions Ni2+, Cu2+, Zn2+, Cd2+ and Pb2+ has also been studied. It forms both mono-and bi-nuclear complexes with Ni2+, Cu2+, Zn2+ and Cd2+ whereas only mononuclear species were found for Pb2+. The electrochemical behaviour of L1 has been studied in CH2Cl2 and water, E1/2 is pH-dependent and from the E1/2 vs. pH curve the protonation constants of oxidized L1 (FeIII) were determined. Similar electrochemical experiments were carried out for L1-H+-M2+ systems. The good agreement between the E1/2 vs. pH and z vs. pH curves (z = average charge calculated from potentiometric data) appears to suggest that the ferrocene-substrate interaction is mainly electrostatic.

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Negative-feedback scanning electrochemical microscopy (SECM) is successfully applied to visualize spatially resolved differences in the topography of coated metal samples upon exposure to aqueous electrolyte solutions of different composition. This method allows the investigation of the uptake of reactants from the electrolyte phase through the polymeric matrix to the metal/polymer interface to be performed even at early exposures. Yet, the method must be carefully checked to discard transport processes from the organic matrix into the solution phase, such as those related to lixiviation. In this later case, the topography of the polymer layer may evolve with time accordingly, not longer exclusively responding to the uptake by the polymer matrix of components from the electrolyte phase. Furthermore, lixiviated species may also react with the SECM tip, eventually leading to the continuous modification of the active surface area of the electrode during the measurements. In this work, the effect of lixiviation from a nickel foil coated with plasticized PVC (PVC Plastisol) on its topographic characterization by SECM was investigated.

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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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 pi -pi* 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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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion