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Superbase-catalyzed (KOH/DMSO suspension as a catalyst) vinylation of hydroxymethyl- and hydroxyethylferrocenes with terminal and internal alkynes (acetylene, propyne, phenylacetylene, 3-ethynylpyridine, 1-propyn-1-yl-benzene, diphenylacetylene) affords hitherto unknown vinyl ethers of ferrocene in 30-93% yields depending on the alkyne structure and the tuneable ratio of reactants/KOH/DMSO. The vinylation smoothly proceeds under mild conditions (70-90 C, 0.25-13 h). With unsubstituted acetylene the process is readily realized under atmospheric pressure (yield of the corresponding vinyl ethers is 81-90%) though under pressure (initial pressure at room temperature is 10-13 atm, maximum pressure is 13-16 atm at the reaction temperature) the yield is close to quantitative (93%). The synthesized compounds were characterized using 1H and 13C NMR, and IR spectroscopy, as well as X-ray diffraction analysis.

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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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Herein, we report the electrocatalytic voltammetry of holo and heme-free human sulfite oxidase (HSO) mediated by the synthetic iron complexes 1,2-bis(1,4,7-triaza-1-cyclononyl)ethane iron(III) bromide, ([Fe(dtne)]Br3.3H2O), potassium ferricyanide (K3[Fe(CN)6]), and ferrocene methanol (FM) at a 5-(4?-pyridinyl)-1,3,4-oxadiazole-2-thiol (Hpyt) modified gold working electrode. Holo HSO contains two electroactive redox cofactors, comprising a mostly negatively charged cyt b5 (heme) domain and a Mo cofactor (Moco) domain (the site of sulfite oxidation), where the surface near the active site is positively charged. We anticipated different catalytic voltammetry based on either repulsive or attractive electrostatic interactions between the holo or heme-free enzymes and the positively or negatively charged redox mediators. Both holo and heme-free HSO experimental catalytic voltammetry has been modeled by using electrochemical simulation across a range of sweep rates and concentrations of substrate and both positive and negatively charged electron acceptors ([Fe(dtne)]3+, [Fe(CN)6]3? and FM+), which provides new insights into the kinetics of the HSO catalytic mechanism. These mediator complexes have almost the same redox potential (all lying in the range +415 to +430 mV vs. NHE) and, thus, deliver the same driving force for electron transfer with the Mo cofactor. However, differences in the electrostatic affinities between HSO and the mediator have a significant influence on the electrocatalytic response.

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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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Electrical properties, such as charge propagation, dielectrics, surface potentials, conductivity, and piezoelectricity, play crucial roles in biomolecules, biomembranes, cells, tissues, and other biological samples. However, characterizing these electrical properties in delicate biosamples is challenging. Atomic Force Microscopy (AFM), the so called ?Lab on a Tip? is a powerful and multifunctional approach to quantitatively study the electrical properties of biological samples at the nanometer level. Herein, the principles, theories, and achievements of various modes of AFM in this area have been reviewed and summarized. Statement of Significance: Electrical properties such as dielectric and piezoelectric forces, charge propagation behaviors play important structural and functional roles in biosystems from the single molecule level, to cells and tissues. Atomic force microscopy (AFM) has emerged as an ideal toolkit to study electrical property of biology. Herein, the basic principles of AFM are described. We then discuss the multiple modes of AFM to study the electrical properties of biological samples, including Electrostatic Force Microscopy (EFM), Kelvin Probe Force Microscopy (KPFM), Conductive Atomic Force Microscopy (CAFM), Piezoresponse Force Microscopy (PFM) and Scanning ElectroChemical Microscopy (SECM). Finally, the outlook, prospects, and challenges of the various AFM modes when studying the electrical behaviour of the samples are discussed.

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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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Scanning electrochemical microscopy (SECM) and copper staining are combined to achieve visualisation of proteins on surfaces. Proteins are adsorbed on a polyvinylidene fluoride (PVDF) membrane or on a polyethylene terephthalate (PET) surface and stained using a standard protocol involving copper salts. Salts are then reduced to copper and detected by SECM with ferrocene methanol as a redox mediator in aqueous solution. During the SECM scan, the potential is held at a value at which the oxidation of the redox mediator occurs and a positive feedback current is detected when scanning over copper clusters. A negative feedback is observed elsewhere. This method enables unspecific protein adsorption mapping on polymeric membranes and into microchannels without any requirement of enzymatic activity or affinity to a labelled secondary reporter.

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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 surface of a platinum electrode has been modified with platinum nanoparticles (PtNPs) and the enzyme sulfite oxidase (SOx), was entrapped on its surface in an ultrathin polypyrrole (PPy) film. The PtNPs, with a diameter of 30?40 nm, were deposited on the Pt electrode by cycling the electrode potential 20 times from -200 to 200 mV at a sweep rate of 50 mV.s-1. Morphological evidence of the successful incorporation of SOx and the presence of PtNPs were obtained by scanning electron microscopy. Also, the electrochemical behavior of the PtNPs/PPy-SOx film was examined by cyclic voltammetry, chronopotentiometry, electrochemical impedance spectroscopy and potentiometry. Under optimized conditions, the biosensor achieved a sensitivity of 57.5 mV.decade-1, a linear response that extends from 0.75 to 65 muM of sulfite, a detection limit of 12.4 nM, and a response time of 3?5 s. The biosensor was successfully applied to the determination of sulfite in wine and beer samples. [Figure not available: see fulltext.]

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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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Hydrogen peroxide (H2O2) is an important target material for detecting biomolecules including acetylcholine (ACh), glutamate (Glu), and glucose. In this study, we report on H2O2 detection under biological environments based on the redox reaction. The redox potential change caused by the reaction between the electron mediators of ferrocenes and H2O2 catalyzed by horseradish peroxidase (HRP) was measured using a gold electrode connected to a source follower circuit. The mediators were either dissolved in sample solutions using ferrocenyl methanol (FcMeOH) or immobilized on the sensor surface in the form of 11-ferrocenyl-1- undecanethiol (11-FUT). H2O2 detection under biological environments was demonstrated in both samples. The overall outputs in the 11-FUT-immmobilzed electrodes were lower than those in the samples with dissolved FcMeOH. The detection range of H2O2 was from 10-5 to 10-3 M for the samples with dissolved FcMeOH, while it was from 10-4 to 10-2 M for the 11-FUT-immobilized electrodes. It was suggested that the oxidation of the mediators by H2O2 insufficiently took place in the 11-FUT-immobilized electrodes, leading to the lower outputs.

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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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This study describes the molecular-level design of a new type of filtration membrane made of crosslinked cyclodextrins?inexpensive macrocycles of glucose, shaped like hollow truncated cones. The channel-like cavities of cyclodextrins spawn numerous paths of defined aperture in the separation layer that can effectively discriminate between molecules. The transport of molecules through these membranes is highly shape-sensitive. In addition, the presence of hydrophobic (cavity) and hydrophilic (ester-crosslinked outer part) domains in these films results in high permeances for both polar and nonpolar solvents.

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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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Diaphorase (DI) works as an effective catalyst for the electrochemical oxidation and reduction of NAD with the aid of several quinones or flavins as electron transfer mediators. The redox kinetics between DI and mediators have been expressed by a Butler-Volmer-type equation. NAD-dependent L-lactate dehydrogenase (LDH) catalyzing the redox reaction between L-lactate and pyruvate was coupled to the DI-catalyzed NAD redox system to achieve better understanding of mediated two-enzyme-linked bioelectrocatalysis with reversible characteristics. Under the conditions where the concentration polarization of NAD due to the DI-catalyzed electrochemical reaction is suppressed by the LDH reaction, the NAD concentration dependence of the catalytic current was expressed by an approximate equation involving the enzyme kinetics between DI and NAD. The suppression of the NAD concentration polarization is also useful to observe steady-state catalytic waves of an uphill reaction between DI and the mediator. The oxidation reaction involving the uphill electron transfer from L-lactate to NAD+ is susceptible to a inhibition from pyruvate due to the reversible characteristics of LDH. The present knowledge has led to the strategy to realize a two-way bioelectrocatalysis for the reduction of pyruvate and the oxidation of L-lactate. New potentiometry for the detection of the solution potential governed by the electrochemically inactive pyruvate/L-lactate redox couple has also been demonstrated based on the reversible characteristics of the DI-DLH-linked bioelectrocatalytic system.

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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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Regioselectivity of ferrocenylalkylation reaction of mercaptoheterocycles with ferrocenylcarbinoles in biphasic aqueous-organic media was studied. The structures of compounds were assigned on the basis of NMR spectra and 1H/13C heteronuclear correlations. X-ray determination of molecular structures of 1-(ferrocenyl(phenyl)methyl)pyrrolidine-2-thione 5f, 4, 5-dihydro-1-(1-ferrocenylmethyl)-1H-imidazole-2-thiol 7a and 4, 5-dihydro-1-(1-ferrocenyl-2methylpropyl)-1H-imidazole-2-thiol 7e were carried out.

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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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A series of ferrocene-appended half-sandwiched iridium(III) phenylpyridine complexes have been designed and synthesized. These complexes show better anticancer activity than cisplatin widely used in clinic under the same conditions. Meanwhile, complexes could effectively inhibit cell migration and colony formation. Complexes could interact with protein and transport through serum protein, effectively catalyzing the oxidation of nicotinamide-adenine dinucleotid and inducing the accumulation of reactive oxygen species (ROS, 1O2), which confirmed the anticancer mechanism of oxidation. Furthermore, laser scanning confocal detection indicates that these complexes can enter cells followed by a non-energy-dependent cellular uptake mechanism, effectively accumulating in the lysosome (Pearson’s colocalization coefficient: ?0.90), leading to lysosome damage, and reducing the mitochondrial membrane potential (MMP). Taken together, ferrocene-appended iridium(III) complexes possess the prospect of becoming a new multifunctional therapeutic platform, including lysosome-targeted imaging and anticancer drugs.

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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