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Journal articles on the topic 'Ferrocene Chemistry'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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1

Snegur, Lubov V. "Modern Trends in Bio-Organometallic Ferrocene Chemistry." Inorganics 10, no. 12 (November 26, 2022): 226. http://dx.doi.org/10.3390/inorganics10120226.

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Organometallic sandwich compounds, especially ferrocenes, possess a wide variety of pharmacological activities and therefore are attracting more and more attention from chemists, biologists, biochemists, etc. Excellent reviews concerning biological aspects and design of ferrocene-modified compounds appear regularly in scientific journals. This brief overview highlights recent achievements in the field of bio-organometallic ferrocene chemistry from 2017 to 2022. During this period, new ferrocene-modified analogues of various bio-structures were synthesized, namely, betulin, artemisinin, steroids, and alkaloids. In addition, studies of the biological potential of ferrocenes have been expanded. Since ferrocene is 70 years old this year, a brief historical background is also given. It seemed to me useful to sketch the ‘ferrocene picture’ in broad strokes.

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2

Nakamura, E. "Bucky ferrocene. Hybrid of ferrocene and fullerene." Pure and Applied Chemistry 75, no. 4 (January 1, 2003): 427–34. http://dx.doi.org/10.1351/pac200375040427.

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The idea of “bucky ferrocene” intrigues chemists owing to its aesthetic beauty and to its polarized, extended conjugated system, but the idea has remained hypothetical. The synthesis of close analogs of Fe(C60Me5)Cp and Fe(C70Me3)Cp was achieved in two steps from [60] and [70]fullerenes, relying on an oxidative C–H bond activation starting with an iron(I) complex and the corresponding cyclopentadienyl precursors, respectively. The molecules can be regarded as members of a new organometallic conjugated system connected to a graphitic system. Numerous synthetic transformations and self-organization procedures that are known for the parent ferrocenes and fullerenes are expected to be employable toward productive use of the ferrocene/fullerene hybrid molecules in chemistry and materials sciences.

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3

Prokop, Petra, Rainer Richter, and Lothar Beyer. "Zur Reaktion von 2,4-Dioxo-4-ferrocenyl-butansäureethylester mit primären aromatischen Aminen / On the Reaction of Ethyl 2,4-Dioxo-4-ferrocenyl-butanoate with Primary Aromatic Amines." Zeitschrift für Naturforschung B 54, no. 7 (July 1, 1999): 849–57. http://dx.doi.org/10.1515/znb-1999-0705.

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Starting from ethyl 2,4-dioxo-4-ferrocenyl-butanoate (1) a series of new ferrocene derivatives has been prepared. While the reaction with o-phenylene diamine leads to two ferrocene-containing heterocyclic compounds, 4-ferrocenyl-3H-1,5-benzodiazepine-2-carbonic acid ethyl ester (3) and 3-(2-ferrocenyl-2-oxo-ethylidene)-3,4-dihydro-1H-quinoxalin-2-one · H20 (4), reactions with m- and p-phenylene diamine give both the mono- and disubstituted products 5 - 8, respectively. The conversion of 4 by Lawesson’s reagent results in 2-ferrocenvl-thieno[2,3- b]quinoxaline (9). The new compounds have been characterized by their 1H, 13C NMR, and mass spectra. The molecular structures of 4-ferrocenyl-4-oxo-2-phenylamino-but-2-enoic acid ethyl ester 2, and of 4 and 9 have been determined by X-ray crystal structure analysis.

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4

Apreutesei, Daniela, Gabriela Lisa, Natalia Hurduc, and Dan Scutaru. "Synthesis and un-isotherm kinetic study of some ferrocene acids." Open Chemistry 2, no. 4 (December 1, 2004): 553–62. http://dx.doi.org/10.2478/bf02482720.

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AbstractThe goal of this paper is to study thermal stability of some ferrocenes with acidic functional groups. Some other kinetic characteristics such as critical temperature and the rate constant corresponding to maximal degradation speed have been also evaluated. The type of functional units adjacent to the ferrocenyl unit determines thermal stability of ferrocene compounds. Groups with a powerful withdrawing effect determine a decreasing of the temperatures at which the material starts to lose weight. If a very long alkyl chain is connected to the ferrocene unit, a shielding effect in respect to the other carboxylic groups was observed, with an increase of the thermal stability.

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5

Rauf, Umair, Ghulam Shabir, Saba Bukhari, Fernando Albericio, and Aamer Saeed. "Contemporary Developments in Ferrocene Chemistry: Physical, Chemical, Biological and Industrial Aspects." Molecules 28, no. 15 (July 30, 2023): 5765. http://dx.doi.org/10.3390/molecules28155765.

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Ferrocenyl-based compounds have many applications in diverse scientific disciplines, including in polymer chemistry as redox dynamic polymers and dendrimers, in materials science as bioreceptors, and in pharmacology, biochemistry, electrochemistry, and nonlinear optics. Considering the horizon of ferrocene chemistry, we attempted to condense the neoteric advancements in the synthesis and applications of ferrocene derivatives reported in the literature from 2016 to date. This paper presents data on the progression of the synthesis of diverse classes of organic compounds having ferrocene scaffolds and recent developments in applications of ferrocene-based organometallic compounds, with a special focus on their biological, medicinal, bio-sensing, chemosensing, asymmetric catalysis, material, and industrial applications.

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6

Fleischer, Ivana, and Štefan Toma. "Synthesis of New Chiral 1,2-Disubstituted Ferrocenes." Collection of Czechoslovak Chemical Communications 69, no. 2 (2004): 330–38. http://dx.doi.org/10.1135/cccc20040330.

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Synthesis of six chiral 1,2-disubstituted ferrocene derivatives is described starting from (S)-{[2-(methoxymethyl)pyrrolidin-1-yl]methyl}ferrocene (2) and {[N-((1R,2S)-methoxy-1-methyl-2-phenethyl)-N-methylamino]methyl}ferrocene (3). Oxidation of the (N-substituted aminomethyl)ferrocenes with active MnO2 furnished the corresponding 2-substituted ferrocenecarbaldehydes.

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7

Rajakumar, Perumal, Ramasamy Anandhan, and Ayyavoo Kannan. "1,2,3-Triazole Ferrocenyldendrimers Through Click Chemistry Approach and their Optical and Electrochemical Properties." Australian Journal of Chemistry 65, no. 10 (2012): 1457. http://dx.doi.org/10.1071/ch12166.

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Novel ferrocenyl dendrimers with ferrocene as a surface group and with triazole as a bridging unit have been synthesised through click chemistry. The increasing numbers of triazole and ferrocenyl units at the antenna increase the light absorbing ability. The electrochemical behaviour changes with increasing ferrocenyl and triazole units.

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8

Sobociková, Marie, Petr Štěpnička, Daniele Ramella, and Martin Kotora. "Synthesis of 1-Alkanoyl-1'-(trifluoroacetyl)ferrocenes." Collection of Czechoslovak Chemical Communications 71, no. 2 (2006): 190–96. http://dx.doi.org/10.1135/cccc20060190.

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Synthesis of the first representatives of mixed acyl(perfluoroacyl)ferrocenes, 1-acetyl-1'-(trifluoroacetyl)ferrocene (3a) and 1-propionyl-1'-(trifluoroacetyl)ferrocene (3b), by stepwise Friedel-Crafts acylation is described. A comparison of redox potentials of acetylferrocene, (trifluoroacetyl)ferrocene, and 3a as determined by cyclic voltammetry shows that the substitution effect is not purely additive.

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9

Sinha, Neeta. "Synthesis of 3-Ferrocenyl Isocoumarins." Oriental Journal Of Chemistry 36, no. 05 (October 25, 2020): 976–79. http://dx.doi.org/10.13005/ojc/360527.

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The derivatives of 3-ferrocenyl isocoumarin were synthesized by the condensation of substituted homothphalic anhydride with ferrocene using phosphoric acid or anhydrous aluminium chloride as cyclising agent. Substituted homophthalic acid did not condense with ferrocene so homophthalic acids were converted into their anhydride and then allowed to react with ferrocene in the presence of polyphosphoric acid or in the presence of anhydrous aluminium chloride using dichloromethane as the solvent to give 3-ferrocenyl isocoumarins. 7-Methoxy, 6-methyl, 5,7-dihydroxy, 6,7-dimethoxy and 5,7-dimethoxy derivatives of 3-ferrocenyl isocoumarin were synthesized. All the compounds were characterised by melting point determination, elemental and spectral analysis.

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10

Montes-González, Ingrid, Ambar M. Alsina-Sánchez, Juan C. Aponte-Santini, Sara M. Delgado-Rivera, and Geraldo L. Durán-Camacho. "Perspectives of ferrocenyl chalcones: synthetic scaffolds toward biomedical and materials science applications." Pure and Applied Chemistry 91, no. 4 (April 24, 2019): 653–69. http://dx.doi.org/10.1515/pac-2018-0802.

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Abstract Ferrocene and its derivatives constitute versatile and interesting scaffolds for the global chemical enterprise due to its multiple applications that range from biomedical to materials science. Ferrocenyl derivatives are the leading compounds in our research for the syntheses and characterization as well as their potential biological applications. Among them, our recent focus has been in ferrocenyl chalcones as a framework for further derivatization. The proposed modifications consist on the incorporation of heterocyclic moieties into the ferrocenyl chalcone core. This can be afforded either by introducing a heterocyclic aromatic moiety as a substituent or functionalizing the α-β unsaturated system. Another modification explored is the formation of ammonium or pyridinium salts to increase water solubility. Studied ferrocenyl chalcones exhibit remarkable stability, physical, and electrochemical properties. These factors have led the approaches for them to be precursors of biologically active compounds (cancer, bacteria, malaria, and neurobiological diseases). Moreover, other potential applications include molecular materials, redox-sensors, and polymers. Our goal in this mini review is to highlight the chemistry of ferrocene derivatives with particular prominence to those ferrocenyl chalcones studied in our laboratory and their applications. Moreover, we are providing a background on ferrocene, chalcones, and ferrocenyl chalcones, emphasizing the methodologies with preeminent yields.

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11

Turrin, Cédric-Olivier, Eric Manoury, and Anne-Marie Caminade. "Ferrocenyl Phosphorhydrazone Dendrimers Synthesis, and Electrochemical and Catalytic Properties." Molecules 25, no. 3 (January 21, 2020): 447. http://dx.doi.org/10.3390/molecules25030447.

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The discovery of ferrocene is often associated with the rapid growth of organometallic chemistry. Dendrimers are highly branched macromolecules that can be functionalized at will at all levels of their structure. The functionalization of dendrimers with ferrocene derivatives can be carried out easily as terminal functions on the surface, but also at the core, or at one or several layers inside the structure. This review will focus on phosphorhydrazone dendrimers functionalized with ferrocene derivatives, on the surface, at the core, at all layers or within a single layer inside the structure. The first part will describe the synthesis; the second part will concern the electrochemical properties; and the last part will give several examples concerning catalysis, with complexes of ferrocenyl phosphines used as terminal functions of dendrimers.

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12

Sørensen, Thomas, and Merete Nielsen. "Synthesis, UV/vis spectra and electrochemical characterisation of arylthio and styryl substituted ferrocenes." Open Chemistry 9, no. 4 (August 1, 2011): 610–18. http://dx.doi.org/10.2478/s11532-011-0040-8.

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AbstractTwo series of substituted ferrocenes were synthesised using either the Horner-Wadsworth-Emmons reaction or monolithiation of ferrocene. The series consist of arylthio- and styryl-ferrocenes with different substituents in the para position of the aryl rings of the systems. The electronic communication was investigated by comparing the substituent effects in absorption spectroscopy and in cyclic voltammetry. A small substituent effect was found in the electronic transitions of the styryl substituted ferrocenes. The oxidation of the ferrocene derivatives showed clear substituent effects as illustrated by the linear Hammett plots. The effect was shown to be an order of magnitude larger in the arylthio-systems than in the styryl systems. It is suggested that the reason behind the large effect is a direct sulfur-iron orbital overlap.

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13

Wu, Jinsheng, Xiaolong Li, Mingyu Yang, Yujie Gao, Qianru Lv, and Baohua Chen. "Convenient synthesis of ferrocene amines via Cu-catalyzed coupling reaction." Canadian Journal of Chemistry 86, no. 9 (September 1, 2008): 871–74. http://dx.doi.org/10.1139/v08-096.

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An efficient copper-catalyzed Ullmann-type cross-coupling reaction without ligand of iodo-ferrocene with amines has been reported. In this process, a range of ferrocenyl amine compounds have been prepared in moderate to good yields.Key words: amines, iodo-ferrocene, cross-coupling, copper, Ullmann coupling.

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14

Gilbert, Austin B., Matthew R. Crawley, Trevor J. Higgins, Yuguang C. Li, David F. Watson, and Timothy R. Cook. "Exploring the Emergent Redox Chemistry of Pd(II) Nodes with Pendant Ferrocenes: From Precursors, through Building Blocks, to Self-Assemblies." Inorganics 11, no. 3 (March 15, 2023): 122. http://dx.doi.org/10.3390/inorganics11030122.

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Energy-relevant small molecule activations and related processes are often multi-electron in nature. Ferrocene is iconic for its well-behaved one-electron chemistry, and it is often used to impart redox activity to self-assembled architectures. When multiple ferrocenes are present as pendant groups in a single structure, they often behave as isolated sites with no separation of their redox events. Herein, we study a suite of molecules culminating in a self-assembled palladium(II) truncated tetrahedron (TT) with six pendant ferrocene moieties using the iron(III/II) couple to inform about the electronic structure and, in some cases, subsequent reactivity. Notably, although known ferrocene-containing metallacycles and cages show simple reversible redox chemistry, this TT undergoes a complex multi-step electrochemical mechanism upon oxidation. The electrochemical behavior was observed by voltammetric and spectroelectrochemical techniques and suggests that the initial Fc-centered oxidation is coupled to a subsequent change in species solubility and deposition of a film onto the working electrode, which is followed by a second separable electrochemical oxidation event. The complicated electrochemical behavior of this self-assembly reveals emergent properties resulting from organizing multiple ferrocene subunits into a discrete structure. We anticipate that such structures may provide the basis for multiple charge separation events to drive important processes related to energy capture, storage, and use, especially as the electronic communication between sites is further tuned.

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15

Ermolaev, Vadim V., Liliya R. Kadyrgulova, Mikhail N. Khrizanforov, Tatiana P. Gerasimova, Gulnaz R. Baembitova, Anna A. Lazareva, and Vasili A. Miluykov. "Conductive Mediators in Oxidation Based on Ferrocene Functionalized Phosphonium Ionic Liquids." International Journal of Molecular Sciences 23, no. 24 (December 8, 2022): 15534. http://dx.doi.org/10.3390/ijms232415534.

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Herein, the synthesis of ferrocene-containing salts is presented. Acylation of ferrocene (Fc) according to the Friedel–Crafts method led to ω-bromoacyl ferrocenes. The ω-bromoacyl ferrocenes were subsequently introduced to quaternization reaction with tri-tert-butyl phosphine, which resulted in phosphonium salts. Obtained phosphonium salts were characterized by physical methods. The electrochemical properties of phosphonium salts were studied by cyclic voltammetry (CV). It was found that the replacement of n-butyl fragments at the phosphorus atom by tert-butyl leads to a more anodic potential shift. In contrast to isolobal structures Fc-C(O)(CH2)nP+(n-Bu)3X− and Fc-(CH2)n+1P+(n-Bu)3X−, the CV curves of Fc-C(O)(CH2)nP+(t-Bu)3X− and Fc-(CH2)n+1P+(t-Bu)3X− did not show a large discrepancy between forward and reverse currents. The transformation of the C=O groups to CH2 fragments had a significant effect on the electrochemical properties of ferrocene salts, the oxidation potential of which is close to that of pure ferrocene.

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16

Gao, Li Ming, Ramón Hernández, Jaime Matta, and Enrique Meléndez. "Synthesis, Structure, Electrochemistry, and Cytotoxic Properties of Ferrocenyl Ester Derivatives." Metal-Based Drugs 2009 (March 24, 2009): 1–8. http://dx.doi.org/10.1155/2009/420784.

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A series of ferrocenyl ester complexes, varying the lipophilic character of the pendant groups, was prepared and characterized by spectroscopic and analytical methods. The syntheses of Fe(C5H4CO2CH3)2, Fe(CpCOOCH3) (CpCOO CH2CH3), and Fe(CpCOOCH2CH3)2 are reported. The solid-state structure of Fe(C5H4CO2CH3)2 has been determined by X-ray crystallography. Fe(C5H4CO2CH3)2 has the cyclopentadienyl rings virtually in an eclipsed conformation with the pendant groups not completely opposite to each other. Cyclic voltammetry characterization showed that the functionalized ferrocenes oxidize at potentials, Epa, higher than ferrocene as a result of the electro withdrawing effect of the pendant groups on the cyclopentadienyl ligand. The cytotoxicities of Fe(C5H4CO2CH2CH2OH)2, Fe(C5H4CO2CH2CH=CH2)2, Fe(C5H4CO2CH3)2, Fe(CpCOOCH3)(CpCOOCH2CH3), and Fe(CpCOOCH2CH3)2 in colon cancer HT-29 and breast cancer MCF-7 cell lines were measured by the MTT biological viability assay and compared to ferrocene and ferrocenium. Fe(C5H4CO2CH2CH=CH2)2 showed the best IC50 values, 180(10) μM for HT-29 and 190(30) μM for MCF-7 cell lines, with cytotoxicities similar to ferrocenium. The cytotoxic data suggest that as we increase the lipophilic character of the functionalized ferrocene, the cytotoxicity improves approaching to the cytotoxic activity of ferrocenium.

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17

Frey, Guido D., and Stephan D. Hoffmann. "Synthesis of ferrocenyl aryl ethers via Cu(I)/phosphine catalyst systems." Zeitschrift für Naturforschung B 70, no. 1 (January 1, 2015): 65–70. http://dx.doi.org/10.1515/znb-2014-0178.

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AbstractFerrocenyl aryl ethers can be synthesized in good yields by Cu(I)/phosphine-catalyzed coupling reactions from iodoferrocene or 1,1′-dibromoferrocene and various phenols in toluene, using Cs2CO3 or K3PO4 as a base. For the first time a solid-state structure of a ferrocenyl-1,1′-diaryl ether [1,1′-di(4-tert-butylphenoxy)ferrocene] has been determined from single-crystal X-ray data. The mixed ferrocenyl aryl ether 1-(4-tert-butylphenoxy)-1′-(2,4-dimethylphenoxy)ferrocene was prepared in a two-step synthetic protocol.

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18

Honegger, Philipp, Alexander Roller, and Michael Widhalm. "Synthesis and characterization of enantiopure planar–chiral phosphorus-linked diferrocenes." Acta Crystallographica Section C Structural Chemistry 77, no. 3 (February 25, 2021): 152–60. http://dx.doi.org/10.1107/s2053229621001996.

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In the course of an ongoing synthetic project on cyclic diferrocenylphosphines, we obtained a group of planar–chiral diferrocenyl compounds useful as precursors for subsequent cyclization. Here we report the crystal structures of two symmetric compounds [(FcA)2(Ph)P], one of which contains four stereogenic centres (two C chiral and two planar chiral centres), i.e. 1,1′-(phenylphosphanediyl)bis{(2S p)-2-[(1R)-1-(acetyloxy)ethyl]ferrocene}, [Fe2(C5H5)2(C24H25O4P)], and the other phosphine sulfide is a purely planar–chiral compound (two planar chiral centres), i.e. bis[(2S p)--2-ethenylferrocen-1-yl]phenylphosphane sulfide, [Fe2(C5H5)2(C20H17PS)]. Owing to the stereocentres present, reactions performed on [(FcA)2(Ph)P]-type compounds strongly favour one ferrocene unit over the other due to diastereoselectivity. Furthermore, we present four related structures where the ferrocene units are not identical [(FcA)(FcB)(Ph)P]. These are {(2S p)-2-[(1R)-1-(acetyloxy)ethyl]ferrocen-1-yl}[(2S p)-2-ethenylferrocen-1-yl]phenyl-(S)-phosphine sulfide, [Fe2(C5H5)2(C22H21O2PS)], [(2S p)-2-ethenylferrocen-1-yl]{(2S p)-2-[(1R)-1-hydroxyethyl]ferrocen-1-yl}phenyl-(S)-phosphine sulfide, [Fe2(C5H5)2(C20H19OPS)], {(2S p)-2-[(1R)-1-(acetyloxy)ethyl]ferrocen-1-yl}{(2S p)-2-[(1R)-1-hydroxyethyl]ferrocen-1-yl}phenyl-(R)-phosphine sulfide, [Fe2(C5H5)2(C22H23O3PS)], and {(2S p)-2-[(1R)-1-benzylamino)ethyl]ferrocen-1-yl}[(2S p)-2-ethenylferrocen-1-yl]phenyl-(S)-phosphine sulfide, [Fe2(C5H5)2(C27H26NPS)]. All of the structures are accessible in one step from known precursors.

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19

Toma, Štefan, Martin Putala, and Marta Sališová. "Ultrasound-accelerated synthesis of ferrocene-containing pyrimidine derivatives." Collection of Czechoslovak Chemical Communications 52, no. 2 (1987): 395–98. http://dx.doi.org/10.1135/cccc19870395.

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The base-catalysed addition of thiourea to ferrocene analogues of chalcones is faster and more selective when the reaction mixture is sonicated than when merely heated. 4-Aryl-6-ferrocenyl- and 6-aryl-4-ferrocenyl-3,4-dihydropyrimidine-2(1H)-tyhiones were isolated in 58-79% yields.

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20

Mou, Qi, Ruyuan Zhao, Ruihan Niu, Seiya Fukagawa, Taiki Shigeno, Tatsuhiko Yoshino, Shigeki Matsunaga, and Bo Sun. "Cp*Ir(iii)/chiral carboxylic acid-catalyzed enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates." Organic Chemistry Frontiers 8, no. 24 (2021): 6923–30. http://dx.doi.org/10.1039/d1qo01344k.

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An achiral Cp*Ir(iii)/chiral carboxylic acid-catalysed enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates was achieved, providing planar chiral alkylated ferrocenes in up to 94 : 6 er.

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21

Srivastava, Prakash C., Sangeeta Bajpai, Rajesh Kumar, Shikha Srivastava, Vikas Singh, Shrinkhala Dwivedi, and Ray J. Butcher. "Synthesis and characterization of bis(ferrocenylcarboxylato)telluranes." Canadian Journal of Chemistry 85, no. 7-8 (July 1, 2007): 534–39. http://dx.doi.org/10.1139/v07-073.

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A convenient route to the synthesis of the first bis(ferrocenyl carboxylato) telluranes has been developed. Reactions of 1,1,2,3,4,5,6-heptahydro-1,1-(dihydroxo)tellurane and 1,1,2,3,4,5-hexahydro-1,1-(dihydroxo)tellurophene with ferrocene carboxylic acid give 1,1,2,3,4,5,6-heptahydro-1,1-bis(ferrocenyl carboxylato)tellurane (3) and 1,1,2,3,4,5,-hexahydro-1,1-bis(ferrocenyl carboxylato)tellurophene (5), respectively. The X-ray structure of 3 shows that it contains a tellurium heterocycle (C5H10Te), present in a chair conformation, sandwiched between two ferrocene units with carboxylate groups acting as spacers. Compound 3 also exhibits modest second harmonic generation (SHG) efficiency. The electrochemical studies of 3 and 5 through cyclic voltammetry show only one oxidation wave, indicating the presence of independent redox centers leading to reversible single-step two-electron redox systems.Key words: tellurane, ferrocenylcarboxylate, SHG efficiency, electrochemistry.

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22

Shi, Yan-Chao, Rong-Fei Yang, De-Wei Gao, and Shu-Li You. "Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes." Beilstein Journal of Organic Chemistry 9 (September 18, 2013): 1891–96. http://dx.doi.org/10.3762/bjoc.9.222.

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When Boc-L-Val-OH was used as a ligand for the enantioselective Pd(II)-catalyzed annulation of N,N-substituted aminomethyl ferrocene derivatives with diarylethynes, ferrocenes with planar chirality could be achieved with excellent enantioselectivity (up to 99% ee).

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23

Blömker, Tobias, Philipp Böckmann, Gerald Kehr, Roland Fröhlich, and Gerhard Erker. "Synthesis and Reactions of Ferrocenyl-capped Long-chain Alkynes." Zeitschrift für Naturforschung B 64, no. 6 (June 1, 2009): 587–94. http://dx.doi.org/10.1515/znb-2009-0602.

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Alkyl-substituted acetylenes and diacetylenes with terminal ferrocenyl groups were synthesised starting from ferrocene. The reactivity of the triple bonds in the resulting compounds was used to prepare cobalt-alkyne complexes. Cyclotrimerisation of the monoacetylene resulted in a hexa-substituted benzene derivative with six pending ferrocenyl groups.

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24

Auch, Tanja-Corinna, Holger Braunschweig, Krzysztof Radacki, Rainer Sigritz, Ulrich Siemeling, and Sascha Stellwag. "Synthesis and Crystal Structure of 1,3-Diphenyl-2-ferrocenyl-1,3,2-diazabora-[ 3]ferrocenophane." Zeitschrift für Naturforschung B 63, no. 7 (July 1, 2008): 920–22. http://dx.doi.org/10.1515/znb-2008-0718.

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25

Wrackmeyer, Bernd, Udo Dörfler, Joachim Rinck, and Max Herberhold. "Borylation of 1,1′-Dibromoferrocene and Alkylferrocenes." Zeitschrift für Naturforschung B 49, no. 10 (October 1, 1994): 1403–6. http://dx.doi.org/10.1515/znb-1994-1016.

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Abstract1,1′-Dibromoferrocene (1) and alkylferrocenes (ethylferrocene 2a, n-butyiferrocene 2b) react stepwise with an excess of boron tribromide in hexane to give first the monoborylated ferrocenes (3, 5a, 6a) followed by the diborylated ferrocenes (4, 7a, 8a). In the case of 4, two diastereomers are obtained. The triborylated ferrocene derivatives 9a,b are obtained in high yield as the final products. The proposed structures of all borylated ferrocenes are supported by a consistent set of 1H, 13C and 11B NMR data.

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26

Maria Azeem, Maria Azeem, Jahangeer Ali Patujo Jahangeer Ali Patujo, Saira Fatima Saira Fatima, Amin Badshah Amin Badshah, and Laiba Saleem and Saif ur Rehman Laiba Saleem and Saif ur Rehman. "New Ferrocene Based Thiourea and Guanidines: Synthesis, Structural Elucidation, Aggregation Properties, DNA Binding Studies, and DFT calculations." Journal of the chemical society of pakistan 41, no. 6 (2019): 1126. http://dx.doi.org/10.52568/000817/jcsp/41.06.2019.

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One new ferrocenyl thiourea and four new ferrocene-based alkyl guanidines have been successfully synthesized and well characterized by FT-IR, 1H and 13C NMR. Aggregation properties of ferrocene-based guanidines have been assessed by determining their critical micelles concentration through tensiometry and UV-Visible spectroscopy in the ethanol solution. The results obtained through both the techniques were in close agreement. DFT calculations were performed to calculate the charges distribution, EHOMO, ELUMO and band gaps of synthesized compounds which were further supported through UV-Visible spectroscopy. Due to the ability of ferrocene and guanidine compounds to bind with DNA, their DNA binding studies were performed through cyclic voltammetry and UV-Visible spectroscopy. Binding constant values of the guanidine derivatives are higher than the thiourea and have a linear dependence on the lipophilicity.

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27

van Staveren, Dave R., and Nils Metzler-Nolte. "Bioorganometallic Chemistry of Ferrocene." Chemical Reviews 104, no. 12 (December 2004): 5931–86. http://dx.doi.org/10.1021/cr0101510.

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28

Togni, Antonio. "70 Years Ferrocene!" CHIMIA International Journal for Chemistry 75, no. 9 (September 15, 2021): 805–6. http://dx.doi.org/10.2533/chimia.2021.805.

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Some of the most important features of ferrocene chemistry – structure, reactivity, redox properties, and applications – are presented. Their value in the context of conveying many fundamental aspects of molecular chemistry is considered.

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29

Supej, Michael J., Elizabeth A. McLoughlin, Jesse H. Hsu, and Brett P. Fors. "Reversible redox controlled acids for cationic ring-opening polymerization." Chemical Science 12, no. 31 (2021): 10544–49. http://dx.doi.org/10.1039/d1sc03011f.

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A class of ferrocene-derived acid catalysts whose acidity can be altered through reversible oxidation and reduction of the ferrocenyl moiety to chemically and electrochemically control the ROP of cyclic esters is reported.

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30

Jia, Zhen-Sheng, Qiang Yue, Ya Li, Xue-Tao Xu, Kun Zhang, and Bing-Feng Shi. "Copper-catalyzed monoselective C–H amination of ferrocenes with alkylamines." Beilstein Journal of Organic Chemistry 17 (September 28, 2021): 2488–95. http://dx.doi.org/10.3762/bjoc.17.165.

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A copper-catalyzed mono-selective C–H amination of ferrocenes assisted by 8-aminoquinoline is presented here. A range of amines, including bioactive molecules, were successfully installed to the ortho-position of ferrocene amides with high efficiency under mild conditions. A range of functionalized ferrocenes were compatible to give the aminated products in moderate to good yields. The gram-scale reaction was smoothly conducted and the directing group could be removed easily under basic conditions.

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31

Butler, Ian R., and Jean-Louis Roustan. "The synthesis of dipridyl- and 1,10-phenanthrolylferrocenes and bis-N,N′-(2,2′-dipyridyl(6-ferrocenyl-N,N′-2,2′-dipyridyl))ruthenium dichloride." Canadian Journal of Chemistry 68, no. 12 (December 1, 1990): 2212–15. http://dx.doi.org/10.1139/v90-339.

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Ferrocenyldipyridyls and ferrocenyl-o-phenanthrolines have been synthesized by the direct reaction of lithioferrocenes with the appropriate dipyridine or 1,10-phenanthroline. The spectroscopic properties of these potential new ligands are described and the synthesis of bis-2,2′-dipyridyl(6-ferrocenyl-2,2′-dipyridyl)ruthenium dichloride, 8, in its hydrated form is reported. Keywords: ferrocene, dipyridine, phenanthroline, ruthenium.

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32

El-Zohry, Maher F. "Nonconventional Friedel-Crafts Chemistry. VII. On Homoannular and Heteroannular Reactions of Ferrocene with Bifunctional Moieties under Friedel-Crafts Conditions." Collection of Czechoslovak Chemical Communications 58, no. 5 (1993): 1203–7. http://dx.doi.org/10.1135/cccc19931203.

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The utilization of ferrocene in the organic synthesis and its uses in Friedel-Crafts chemistry, together with our interest in this area, prompted us to investigate the reaction of ferrocene with halo acid chlorides and α,β-unsaturated acid chlorides under different Friedel-Crafts conditions with the aim to employ these reactions in the syntheses of polycyclic ferrocene derivatives.

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33

Stevanović, Dragana, Jovana Bugarinović, Marko Pešić, Anka Todosijević, Goran A. Bogdanović, and Ivan Damljanović. "Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction." RSC Advances 11, no. 57 (2021): 36208–14. http://dx.doi.org/10.1039/d1ra07619a.

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34

Wrackmeyer, Bernd, Heidi E. Maisel, and Max Herberhold. "N-Ferrocenyl Amines Bearing Boryl and Silyl Substituents at the Nitrogen Atom, Studied by 57Fe NMR Spectroscopy." Zeitschrift für Naturforschung B 56, no. 12 (December 1, 2001): 1373–75. http://dx.doi.org/10.1515/znb-2001-1221.

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Abstract A series of ferrocene sandwich compounds such as N-ferrocenyl amine, Fc-NH2 (1), the Nsilylated derivatives Fc-NH -SiMe3 (2), Fc- NH -SiMe2H (3), (Fc-NH )2SiMe2 (4), the N-silyl- N-boryl derivatives Fc-N(SiMe3)(9-BBN) (5) (9-BBN = 9-borabicyclo[3.3.1]nonyl) and Fc- N(SiMe3)BEt2 (6), and the N-borylated derivatives Fc-NH -(9-BBN) (7) and Fc-NH -BEt2 (8) were studied by 57Fe NMR spectroscopy. The δ57Fe data reveal that CFcN(pp)π interactions lead to 57Fe nuclear magnetic deshielding (with respect to ferrocene) which is attenuated if competing BN(pp)π bonding becomes efficient (7, 8).

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35

Wrackmeyer, Bernd, Udo Dörfler, and Max Herberhold. "Notizen: Zur Synthese mehrfach borylierter Ferrocene/Synthesis of Polyborylated Ferrocenes." Zeitschrift für Naturforschung B 48, no. 1 (January 1, 1993): 121–23. http://dx.doi.org/10.1515/znb-1993-0124.

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Ferrocene reacts with an excess of boron triiodide or boron tribromide in hexane solution to give mixtures of 1,3,1′-tris- and 1,3,1′,3′-tetrakis- (dihalogenoboryl)ferrocene. The borylation proceeds stepwise, the intermediates being essentially the known dihalogenoborylferrocene and 1,1′-bis- (dihalogenoboryl)ferrocene compounds, although small am ounts of 1,3-bis(dihalogenoboryl)- ferrocene can also be identified. 1H, 11B and 13C NMR data are given.

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36

DAGANI, RON. "FIFTY YEARS OF FERROCENE CHEMISTRY." Chemical & Engineering News 79, no. 49 (December 3, 2001): 37–38. http://dx.doi.org/10.1021/cen-v079n049.p037.

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37

Štěpnička, Petr. "The Multifaceted Chemistry of Ferrocene." European Journal of Inorganic Chemistry 2017, no. 2 (December 29, 2016): 215–16. http://dx.doi.org/10.1002/ejic.201601409.

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38

Sokolov, Viatcheslav I., Marina N. Nefedova, Tatiana V. Potolokova, and Vasily V. Bashilov. "Fullerenes covalently linked to transition metals with organic ligands." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 275–78. http://dx.doi.org/10.1351/pac200173020275.

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Synthesis of molecules combining both fullerene and metallocene moieties separated by some spacer is discussed in connection with the possible intramolecular charge transfer. Two new kinds of spacers, =CH-CO- and -Pd-P-, have been introduced by using the corresponding reactions. Reaction of diazoacetyl ferrocene and cymantrene with C60 has been studied in detail and products characterized. 1,1'-Bis (diazoacetyl) ferrocene gave with C60 1:1 adduct to which the ansa-structure has been assigned on the basis of 1H and 13C NMR spectra. Palladium-h2-C60 complex with a bidentate ferrocenyl diphosphine as a ligand has been also prepared.

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39

Ward, Jon, Saif Al-Alul, Shane Harrypersad, and Daniel A. Foucher. "Synthesis and characterization of a polyferrocenyldistannane." Canadian Journal of Chemistry 92, no. 6 (June 2014): 525–32. http://dx.doi.org/10.1139/cjc-2013-0463.

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The distannyl-bridged poly bis(dimethylstannyl)ferrocene, 5, was synthesized through either the metal-catalyzed intermolecular dehydrogenative condensation of the bis(dimethylstannyl)ferrocene, 6, or the ring-opening polymerization of the distannane-bridged [2]ferrocenophane, 7. Both polymerization strategies yielded compounds displaying NMR (1H, 13C, 119Sn) evidence for a distannane bridged polymer. A modest moderate molecular weight (GPC; Mw = 9.5 × 104 Da, PDI = 1.76) was found for polymer 5 prepared by dehydrogenative condensation. Polymer 5 displayed electronic communication (≈ 0.2 V) between neighbouring iron centers, similar to those reported for monobridged ferrocenyl stannane polymers. Polymer 5 was further characterized by UV–vis spectroscopy, elemental analysis, and modeled with the related distannyl-8 and tristannyl-9 bisferrocenes using DFT at the SDD level of theory.

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40

Hassani, Mina, Amanda Leda, Weronika Porolnik, Michal Falkowski, Tomasz Rębiś, Jaroslaw Piskorz, Lukasz Popenda, et al. "Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents." Molecules 28, no. 13 (July 5, 2023): 5215. http://dx.doi.org/10.3390/molecules28135215.

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Ferrocene is useful in modern organometallic chemistry due to its versatile applications in material sciences, catalysis, medicinal chemistry, and diagnostic applications. The ferrocene moiety can potentially serve many purposes in therapeutics and diagnostics. In the course of this study, (6-bromo-1-oxohexyl)ferrocene was combined with dimercaptomaleonitrile sodium salt to yield a novel maleonitrile derivative. Subsequently, this compound was subjected to an autocyclotetramerization reaction using the Linstead conditions in order to obtain an octaferrocenyl-substituted magnesium(II) sulfanyl porphyrazine. Following that, both compounds—the maleonitrile derivative and the porphyrazine derivative—were subjected to physicochemical characterization using UV-Vis, ES-TOF, MALDI-TOF, and one-dimensional and two-dimensional NMR spectroscopy. Moreover, the sulfanyl porphyrazine was subjected to various photophysical studies, including optical absorption and emission measurements, as well as the evaluation of its photochemical properties. Values of singlet oxygen generation quantum yields were obtained in different organic solvents. The electrochemical properties of the synthesized compounds were studied using cyclic voltammetry. According to the electrochemical results, the presence of electron-withdrawing oxohexyl groups attached to ferrocene afforded significantly more positive oxidation potentials of the ferrocene-based redox process up to 0.34 V vs. Fc+/Fc.

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41

Bandyopadhyay, Uchchhal, Basker Sundararaju, Rinaldo Poli, Eric Manoury, and Jean-Claude Daran. "Synthesis and crystallographic studies of 2-(diphenylphosphinothioyl)-2-(3-oxobut-1-en-yl)ferrocene." Acta Crystallographica Section E Crystallographic Communications 77, no. 8 (July 30, 2021): 853–56. http://dx.doi.org/10.1107/s205698902100760x.

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As a follow-up to our research on the chemistry of disubstituted ferrocene derivatives, the synthesis and the structure of the title compound, 2-(diphenylphosphinothioyl)-2-(3-oxobut-1-en-yl)ferrocene, [Fe(C5H5)(C21H18OPS)], are described. The molecule is built up from a ferrocene unit disubstituted by an S-protected diphenylphosphine group and by a methylvinylketone chain. The crystal structure features weak C—H...O and C—H...S interactions, which build a two-dimensional network. This structure is compared to that of the related disubstituted diphenylphosphino ferrocene.

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42

McAdam, C. John, and Jim Simpson. "Synthesis, crystal structure and Hirshfeld surface analysis of 1-ferrocenylundecane-1,11-diol." Acta Crystallographica Section E Crystallographic Communications 78, no. 2 (January 7, 2022): 149–53. http://dx.doi.org/10.1107/s205698902101358x.

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The racemic title compound, [Fe(C5H5)(C16H27O2)], comprises an α,ω-diol-substituted undecyl chain with a ferrocenyl substituent at at one terminus. The alkane chain is inclined to the substituted ring of the ferrocene grouping by 84.22 (13)°. The ferrocene rings are almost eclipsed and parallel. The crystal structure features O—H...O and C—H...O hydrogen bonds and C—H...π contacts that stack the molecules along the c-axis direction. A Hirshfeld surface analysis reveals that H...H interactions (83.2%) dominate the surface contacts.

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43

Shekurov, Ruslan P., Mikhail N. Khrizanforov, Almaz A. Zagidullin, Almaz L. Zinnatullin, Kirill V. Kholin, Kamil A. Ivshin, Tatiana P. Gerasimova, et al. "The Phosphinate Group in the Formation of 2D Coordination Polymer with Sm(III) Nodes: X-ray Structural, Electrochemical, and Mössbauer Study." International Journal of Molecular Sciences 23, no. 24 (December 8, 2022): 15569. http://dx.doi.org/10.3390/ijms232415569.

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A coordination polymer has been synthesized using ferrocene-based ligand-bearing phosphinic groups of 1,1′-ferrocene-diyl-bis(H-phosphinic acid)), and samarium (III). The coordination polymer’s structure was studied by both single-crystal and powder XRD, TG, IR, and Raman analyses. For the first time, the Mössbauer effect studies were performed on ferrocenyl phosphinate and the polymer based on it. Additionally, the obtained polymer was studied by the method of cyclic and differential pulse voltammetry. It is shown that it has the most positive potential known among ferrocenyl phosphinate-based coordination polymers and metal–organic frameworks. Using the values of the oxidation potential, the polymer was oxidized and the ESR method verified the oxidized Fe(III) form in the solid state. Additionally, the effect of the size of the phosphorus atom substituent of the phosphinate group on the dimension of the resulting coordination compounds is shown.

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44

Muzalevskiy, Vasily M., Aleksei V. Shastin, Alexandra D. Demidovich, Namiq G. Shikhaliev, Abel M. Magerramov, Victor N. Khrustalev, Rustem D. Rakhimov, Sergey Z. Vatsadze, and Valentine G. Nenajdenko. "A new approach to ferrocene derived alkenes via copper-catalyzed olefination." Beilstein Journal of Organic Chemistry 11 (November 3, 2015): 2072–78. http://dx.doi.org/10.3762/bjoc.11.223.

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A new approach to ferrocenyl haloalkenes and bis-alkenes was elaborated. The key procedure involves copper catalyzed olefination of N-unsubstituted hydrazones, obtained from ferrocene-containing carbonyl compounds and hydrazine, with polyhaloalkanes. The procedure is simple, cheap and could be applied for the utilization of environmentally harmful polyhalocarbons. The cyclic voltammetry study of the representative examples of the synthesized ferrocenyl alkenes shows the strong dependence of the cathodic behavior on the amount of vinyl groups: while for the monoalkene containing molecules no reduction is seen, the divinyl products are reduced in several steps.

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45

Artetxe, Beñat, Amaia Iturrospe, Pablo Vitoria, Estibaliz Ruiz-Bilbao, José S. Garitaonandia, and Juan Gutiérrez-Zorrilla. "A Charge-Transfer Salt Based on Ferrocene/Ferrocenium Pairs and Keggin-Type Polyoxometalates." Molecules 23, no. 12 (November 30, 2018): 3150. http://dx.doi.org/10.3390/molecules23123150.

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A new hybrid inorganic-organometallic salt has been obtained from the reaction of the Keggin-type silicotungstate anion with ferrocene in a water/methanol mixture as a result of the partial oxidation of ferrocene molecules to ferrocenium cations. Single-crystal X-ray diffraction analysis reveals the presence of four ferrocenium (FeIII) cations and one ferrocene (FeII) molecule per plenary Keggin anion in the crystal structure of [FeIII (Cp)2]4[SiW12O40]·[FeII(Cp)2]·2CH3OH (1). Compound 1 thus constitutes the first example in the literature in which ferrocenium and ferrocene species coexist in the structure of a polyoxometalate-based salt. The two crystallographically independent ferrocenium species in the asymmetric unit of 1 exhibit different configurations: One displays an eclipsed conformation with ideal D5h symmetry, whereas the conformation in the other one is staggered D5d. The crystal packing of 1 can be best described as an organometallic sub-lattice of ferrocenium and ferrocene species linked by a network of π-π interactions that generates rectangular cavities of about 14 × 10 Å in which strings of Keggin anions and methanol molecules are hosted, further connected to each other via weak OPOM···CMeOH-OMeOH···OPOM type hydrogen bonds. The charge-transfer nature of the salt has been studied by solid-state diffuse reflectance UV-Vis spectroscopy and the presence of magnetically isolated FeIII/FeII centres has been confirmed by Mössbauer spectroscopy. A topological study carried out on all of the pristine ferrocenyl species deposited in the Cambridge Structural Database (CSD) has allowed two main conclusions to be drawn: (1) these species tend to adopt extreme conformations (either eclipsed or staggered) with less than a 15% of examples showing intermediate states and (2) the oxidation state of the iron centres can be unequivocally assigned on the basis of a close inspection of the Fe···Cp distances, which allows ferrocene neutral molecules and ferrocenium cations to be easily distinguished.

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46

Gibson, Vernon C., Nicholas J. Long, Andrew J. P. White, Charlotte K. Williams, and David J. Williams. "Hang-gliding with Ferrocenes: Unusual Coordination Chemistry of 1,1‘-Bis(mesitylthio)ferrocene." Organometallics 19, no. 21 (October 2000): 4425–28. http://dx.doi.org/10.1021/om0004388.

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47

Jia, Lixiang, Xiaobing Liu, An-An Zhang, Tao Wang, Yuanzhao Hua, Heng Li, and Lantao Liu. "Synthesis of planar chiral ferrocenes via a Pd(0)-catalyzed syn-carbopalladation/asymmetric C–H alkenylation process." Chemical Communications 56, no. 11 (2020): 1737–40. http://dx.doi.org/10.1039/c9cc06529f.

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The Pd(0)-catalyzed tandem intermolecular syn-carbopalladation/asymmetric C–H alkenylation reaction of N-ferrocenyl propiolamides with aryl iodides has been realized, generating planar chiral ferrocene[1,2-d] pyrrolinones in good yields.

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48

Kumar, Manoj, Shashi Sharma, Hardeep Singh Tuli, and Rajshree Khare. "A Novel Synthesis, Characterization and Biological Studies of Ferrocenyl Substituted Pyrazoles." Asian Journal of Chemistry 31, no. 12 (November 16, 2019): 2729–32. http://dx.doi.org/10.14233/ajchem.2019.22161.

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It has been discovered that ferrocenyl substituted heterocyclic compounds have wide scope of restorative methodology. The combination of ferrocenyl substituted pyrazole is the new class in these compounds with upgraded natural activity. This work center around blend of ferrocenyl substituted pyrazoles through novel course. The combination of 1-phenyl-3-ferrocenyl-pyrazole was examined including addition-cyclocondensation like response conditions. The response continued through three phases using of expansion cyclo-buildup of acetyl ferrocene with phenyl hydrazine pursued by cyclizing reagent iodine with NaHCO3. In both syntheses, each time single product isolated having good yields (87 and 79 %). Ferrocenyl substituted pyrazoles were examined by spectroscopic techniques (1H NMR, IR, MS) and their biological properties have been screened.

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49

Ürgüt, Ozan Süleyman, Aydin Tavman, and Muazzez Gürgan Eser. "Synthesis, Characterization and Antibacterial Activities of Ferrocene Ligands and Their Binuclear Complexes." Chemistry Journal of Moldova 17, no. 2 (December 2022): 73–83. http://dx.doi.org/10.19261/cjm.2022.957.

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6-Chloro-2-ferrocenyl-1H-benzimidazole and (E)-((4-chloro-2-hydroxyphenylimino)methyl)ferrocene ligands and their Fe(III), Co(II), Cu(II), Zn(II) and Pd(II) complexes were synthesized. The structure of ligands and metal complexes has been investigated by different methods. In addition, magnetic moment, molar conductivity measurements and antibacterial activity of the ligands and the complexes were investigated.

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50

Rockett, Bernard W., and George Marr. "Ferrocene." Journal of Organometallic Chemistry 318, no. 1-3 (January 1987): 231–96. http://dx.doi.org/10.1016/s0022-328x(00)99380-x.

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