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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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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 atomic bond and molecular polarizabilities of some ferrocene derivatives have been calculated using variational method and delta-function electronic wave functions.Scales have been presented, where the derivatives are classified in order of their polarization properties.Common trends and patterns of behaviour are recognized and 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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Vinyl silyl ethers and disiloxanes can now be prepared from aryl-substituted alkenes and related substrates using a silyl-Heck reaction. The reaction employs a commercially available catalyst system and mild conditions. This work represents a highly practical means of accessing diverse classes of vinyl silyl ether substrates in an efficient and direct manner with complete regiomeric and geometric selectivity.

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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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57Fe NMR-spectra of 28 mono and disubstituted ferrocenes with a natural abundance of 57Fe have been measured relative to internal ferrocene.Most of the resonances appear at the high frequency side.The shielding influence of the various substituents is discussed qualitatively. 57Fe shifts are very sensitive to ring tilting as occurring in <3>ferrocenophanes. – Keywords: 57Fe Shifts; Hybridization influence on chemical shifts; Ring tilting

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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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Four new ferrocenyl-flavone complexes were obtained via palladium-catalyzed Heck cross-coupling reactions; (E)-6-ferrocenylvinyl-chromen-4-one (4), (E)-6-ferrocenylvinyl-2-methyl-chromen-4-one (5), (E)-6-ferrocenylvinyl-2- phenyl-chromen-4-one (6) and (E)-6-ferrocenylvinyl-chromen-4-one-3-propionic acid (7). All compounds were characterized by 1H NMR, 13C NMR, IR spectroscopy, high resolution-MS, elemental analysis and cyclic voltammetry. The molecular structure of derivatives 4 and 6 was also confirmed by X-ray crystallography. The biological activity of the complexes was rationalized on the basis of their anticancer and antibacterial properties. The anticancer activity of ferrocenyl-flavones 4 e7 against established human cell lines derived from hematological and solid tumors has been evaluatedin vitro. The following cell lines were investigated: MCF-7 (estrogen receptor-responsive breast adenocarcinoma), MDA-MB-231 (estrogen receptor-negative breast adenocarcinoma), HepG2 (hepatocellular carcinoma) and CCRF-CEM (T lymphoblast-like polymorph cells). All investigated ferrocenyl-flavones show cytotoxicity against CCRF-CEM cell line. The antibacterial activity of the four ferrocenyl-flavones against Gram-positive methicillin-sensitive Staphylococcus aureus (MSSA), methicillin-resistant S. aureus (MRSA), vancomycin-resistant S. aureus (VRSA) and Staphylococcus epidermidis bacterial strains was determined. Our experiments show antibacterial activity for the carboxylic acid derivative 7 against all tested Gram-positive bacterial strains while no activity was detected for the ferrocene-free 6-bromo-chromen-4-one-3-propionic acid.

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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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The quartz crsytal microbalance (QCM) technique is applied to a study of ion and solvent content within poly(vinylferrocene) (PVF) as a function of redox state in various supporting electrolytes.It is concluded that in ClO4(-) and PF6(-) containing electrolytes the oxidation of the film occurs with little and no change in solvent content of the film, respectively.These findings are in agreement with previously postulated phaselike behavior for this system.Multiple peaks are observed in the voltammetry of the PVF film in Cl(-) containing eletrolytes.Based on the concurrent QCM measurements the structure in the voltammetric response is proposed to result from the electrochemically induced dissolution or delamination of the film and a new charge transport (diffusional) situation which results from loss of the film from the surface.The QCM technique is shown to be a powerful tool for the study of process which result in mass changes at solid/liquid interfaces, especially electrode surfaces.

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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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The development of pyridylidene-Cu-complexes and their application in Cu/Pd-catalyzed heteroarylboration of alkenylheteroarenes is reported. The significance of 1,1?-heteroarylalkanes as building blocks for drug discovery, as well as the straightforward and modular sequence to prepare the pyridylidene-Cu-complexes, makes this catalyst and it applications attractive for chemical synthesis. Furthermore, chiral variants of the pyridylidene-Cu-complexes have been prepared and utilized in the enantioselective arylboration of E-alkenes, further demonstrating the value and potential of this class of catalysts.

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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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The first realization of the amino-trimethylenemethane chemistry is reported using a deprotonation strategy to simplify the synthesis of the amino-trimethylenemethane donor in two steps from commercial and inexpensive materials. A broad scope of cycloaddition acceptors (seven different classes) participated in the chemistry, chemo-, regio-, diastereo-, and enantioselectively generating various types of highly valuable complex amino cycles. Multiple derivatization reactions that further elaborated the initial amino cycles were performed without isolation of the crude product. Ultimately, we applied the amino-trimethylenemethane chemistry to synthesize a potential pharmaceutical in 8 linear steps and 7.5 % overall yield, which previously was achieved in 18 linear steps and 0.6 % overall yield.

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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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We describe in this report a systematic electrochemical characterization of the ion-solvent coupling mechanisms of poly(vinyl ferrocene) (PVF) in pure ionic liquid (IL) and 0.1 M IL aqueous solutions. Our study showed that the unique solvation and ionic properties of ILs significantly affected the break-in process and the ion-solvent transport mechanisms of PVF redox switching. A square model that emphasized both faradaic and nonfaradaic processes of PVF was used to explain the unique irreversible break-in effect in the pure ILs. The electrochemical quartz crystal microbalance technique was used to characterize the PVF redox processes in 0.1 M 1-butyl-3-methyl imidazolium tetrafluoroborate and 0.1 M methanesulfonate ILs in which an obvious difference of cyclic voltammogram was observed. Our results suggested the existence of strong IL-polymer interaction in 0.1 M methanesulfonate IL solutions, i.e., not only the anions but also the IL molecules interacted with the PVF matrix. The cations were later removed from the PVF matrix to balance the excessive positive charge in PVF oxidation. Our study confirmed that IL was not only an electrolyte but also a solvent in PVF redox switching processes. Various types of interactions between PVF and the IL, including dispersion, dipole induction, dipole orientation, hydrogen-bonding, or ionic/charge-charge interactions, could significantly change the PVF redox dynamics. Thus, IL tremendous diversity in structural and chemical properties and their distinctive properties offer us an excellent opportunity to explore IL-polymer interactions and to dynamically control the conductive polymer relaxation processes and their redox switching mechanism for various applications.

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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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An asymmetric synthesis of various trifluoromethyl cyclopropanes from olefins, such as vinyl ferrocene, vinyl ethers, vinyl amines, vinyl carbamates and dienes, was achieved by using Ru(ii)-Pheox catalysts. This catalytic system can function at a low catalyst loading (3 mol%) compared with those reported previously, and the desired cyclopropane products are obtained in high yields with excellent diastereoselectivity (up to >99:1) and enantioselectivity (up to 97% ee).

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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