Synthesis Of Ferrocene Research Articles

Ansa–Ferrocene Derivatives as Potential Therapeutics

It has been known since the 1990s that the introduction of a ferrocenyl–type substituent into compounds with proven biological activity can improve their properties. More recently, it was also shown that a carbon bridge connecting the two cyclopentadienyl rings in ferrocene derivatives could enhance the biological properties of the new compounds compared to those without them. However, the synthesis of ferrocenes with this additional linker, known as ansa–ferrocenes, is more difficult due to advanced synthetic protocols and the phenomenon of planar chirality in ring–substituted compounds. As a result, research into the formation of hybrids, conjugates and other ansa–ferrocene derivatives has not been widely conducted. This review discusses the potential biological properties of these units, covering scientific articles published between 1980 and 2024.

Synthesis of Ferrocene−Cyclodextrin, Anthracene−Cyclodextrin, and Pyrene−Cyclodextrin [2]Rotaxane Conjugates and Their Intercomponent Behavior as Observed in NMR Spectroscopy

AbstractFerrocene, anthracene, and pyrene‐terminated alkynylated moieties were reacted with azidized beta‐cyclodextrin derivatives to form supramolecular structures under various conditions. While initial experiments concerning mono‐azidized beta‐cyclodextrin proved difficult to isolate and have limited solubility, their reaction with peracetylated mono‐azidized beta‐cyclodextrin was more facile. Introduction and threading of the macrocycle, dibenzo‐24‐crown‐8 (DB24C8), allowed for [2]rotaxane synthesis. These compounds were characterized by infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS). Among the compounds formed, the ferrocene‐capped species showed promising host‐guest inclusion complexation with the cyclodextrin cavity.

Model-based design and synthesis of ferrocene containing microgels

Modelling and synthesis go hand in hand to efficiently engineer copolymer microgels with various architectures: core–shell structures (with ferrocene mainly in the core or in the shell) and also microgels with homogeneous comonomer distribution.

Synthesis of ferrocene and azobenzene-based copolymers P(FHEMA-co-MAZOHE)s and their redox and photo-responsive properties

Herein, poly(2-(methacryloyloxy) ethyl ferrocene carboxylate-co-(methacrylohydroxyhexane azobenzene)s) (P(FHEMA-co-MAZOHE)s) were prepared by random copolymerization and were characterized by proton nuclear magnetic resonance (1H NMR) and gel permeation chromatography (GPC) to confirm the structures and molecular weights respectively. Thermal variations were analyzed by thermogravimetric (TG), differential thermogravimetric (DTG) and differential scanning calorimetry (DSC) techniques. Finally, redox and photo stimuli-responsive properties were confirmed by cyclic voltammetry (CV) and ultraviolet–visible spectroscopy (UV–vis) respectively. The results revealed that (P(FHEMA-co-MAZOHE)s) can be useful as information storage materials.

Synthesis of Ferrocene- and Azobenzene-Based Epoxy Polymer and Its Film Preparation and Surface Wrinkle Regulation

Synthesis of Ferrocene- and Azobenzene-Based Epoxy Polymer and Its Film Preparation and Surface Wrinkle Regulation

Donor Substituted Pyrazabole Monomers and Dimers: Design, Synthesis and Properties

AbstractWe report the design and synthesis of ferrocene and triphenylamine substituted D–π– A–π–D and D–π–A–π–A–π–D type of symmetrical pyrazabole monomers (3 and 5) and dimers (6 and 7). Their optical, thermal, electrochemical and computational properties were investigated. The electronic absorption spectra of pyrazaboles 3−7 exhibit absorption bands in UV region. The TGA study reveals that pyrazaboles 3−7 show good thermal stability and pyrazabole monomers are thermally more stable as compared to pyrazabole dimers. The electrochemical studies show that pyrazaboles 3−7 exhibits one reversible oxidation and two reduction waves. The theoretical investigation shows that the triphenylamine substituted pyrazaboles (5 and 7) exhibit low HOMO − LUMO gap values compared to ferrocenyl pyrazaboles (3 and 6).

Synthesis of ferrocene- and azobenzene-based compounds for anion recognition

A series of ferrocene- and azobenzene-based compounds with acyl amine groups attached were designed and synthesized to explore their potential application in anion recognition. Their electro- and photo-properties, and the effect of nitro and amine substituents of the benzene ring on anion recognition were studied by UV-vis absorption spectroscopy (UV) and cyclic voltammetry (CV). The results showed that a nitro group substituent has a positive effect on the binding affinity and sensitivity, which might be due to the strong hydrogen bonding interaction between the receptor and the guest, while an amino group substituent has a negative effect on the sensitivity. Furthermore, the shift in the UV-vis absorption spectra was observed as a color change, which can be used for the naked-eye detection of F− and H2PO 4 − .

Synthesis and Electrochemical Characterization of Metallocene–PNA Oligomers

AbstractThe synthesis of ferrocene‐ and cobaltocenium–PNA conjugates with C‐terminal cysteine residues by solid phase methods is described. Melting points with complementary DNA reveal that both metallocenes stabilize the duplex, although to a different extent. The effect is more pronounced when there is an overhang of the DNA at the PNA amino terminus. The conjugates were studied by electrochemical methods in solution. They were also immobilized on Au microelectrodes in self‐assembled monolayers (SAMs) and further characterized electrochemically on the surface. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

Synthesis of ferrocenes with ene-terminus via water-promoted Barbier-like carbonyl allylation using bimetallic copper(II)/tin(II) reagent

Barbier-type γ-regiospecific allylation of formylferrocene ( 1) with allyl bromides in the presence of stannous chloride dihydrate and catalytic cupric chloride in dichloromethane–water (1:1) afforded corresponding ferrocenyl dienes FcCHC(R 1)C(R 2)CH 2 ( 3– 6). On the other hand, similar reactions of 1,1′-bis-formylferrocene ( 2) yielded oxa-bridged [3]-ferrocenophanes having allyl pendants Fc[CH 2C(R 2)CH(R 1)CH-μ(O)-CHCH(R 1)C(R 2)CH 2] ( 8– 11). The latter appear to result from the dehydration of intermediate homoallylic alcohols. Dehydration could be arrested in case of reaction of 1 and 2 with 1-bromo-3-methyl-but-2-ene, which results in the formation of homoallylic alcohols FcCH(OH)C(Me 2)CHCH 2 ( 7) and Fc[CH(OH)C(Me 2)CHCH 2] 2 ( 12), respectively. All the reactions completely fail in absence of water.

A New Preparation of Perdeuterated Ferrocene

A new synthesis of ferrocene- d10 using acid catalysed exchange is described.

Lipase-mediated resolution of 2-hydroxymethyl-1-iodoferrocene: synthesis of ferrocenes and biferrocenes with planar chirality

Racemic 2-hydroxymethyl-1-iodoferrocene (±)- 1 was subjected to esterification in the presence of lipase from Candida antarctica (Novozym ® 435) to afford (1 S,2 S)-2-acetoxymethyl-1-iodoferrocene (−)- 2 having 89% ee and unreacted (1 R,2 R)-2-hydroxymethyl-1-iodoferrocene (+)- 1 in enantiopure form. A single enantiomer of 2-hydroxymethyl-1-iodoferrocene gave easy access to new ferrocenes and biferrocenes possessing only planar chirality.

Synthesis and properties of novel substituted 4,5,6,7-tetrahydroindenes and selected metal complexes

The synthesis of a complete series of substituted 4,5,6,7-tetrahydroindenes (4,5,6,7-tetrahydroindene, 1; 1-methyl-, 1,3-dimethyl- and 1,2,3-trimethyl-4,5,6,7-tetrahydroindene, 2–4) is reported. The synthesis of ferrocenes (bd8–11) from these substituted cyclopentadienes is described. The electrochemistry of these ferrocenes indicates that these complexes are more readily oxidized than ferrocene and that the effect of methyl or alkyl substituents on the ease of oxidation is additive. A single crystal X-ray structure of two of the ferrocenes, bis(1,3-dimethyl-4,5,6,7-tetrahydroindenyl)iron(II), 10, and bis(1,2,3-trimethyl-4,5,6,7-tetrahydroindenyl)iron(II), 10, indicates that steric hindrance causes the alkyl substituents to be bent away from the plane of the cyclopentadienyl ring. However, the structures differ in that the cyclopentadienyl rings in 10 are staggered wheras those in 11 are eclipsed. The synthesis of the cyclopentadienyltricarbonylmethyl compounds of molybdenum and tungsten from 3 and 4 is also described.

ChemInform Abstract: Synthesis of Ferrocene and Cobaltocene Electrode Films by Electropolymerization and Their Spectral and Electrochemical Properties.

AbstractElectroreduction of (I)‐(IV) in MeCN solutions leads to deposition of stable electroactive polymeric films such as (V) (from (I)) on glassy‐carbon and indium tin oxide coated glass electrodes.

Synthesis of ferrocene and cobaltocene electrode films by electropolymerization and their spectral and electrochemical properties

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of ferrocene and cobaltocene electrode films by electropolymerization and their spectral and electrochemical propertiesHiroshi Nishihara, Mitsuhiko Noguchi, and Kunitsugu AramakiCite this: Inorg. Chem. 1987, 26, 17, 2862–2867Publication Date (Print):August 1, 1987Publication History Published online1 May 2002Published inissue 1 August 1987https://doi.org/10.1021/ic00264a029RIGHTS & PERMISSIONSArticle Views785Altmetric-Citations34LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-Alerts Get e-Alerts

Question of thermodynamics of the direct synthesis of ferrocene

Question of thermodynamics of the direct synthesis of ferrocene

Production of organometallic polymers by the interfacial technique. XXX. Synthesis of oligomeric ferrocene containing tin polyesters

AbstractThe synthesis of ferrocene containing polyesters is reported along with particular reaction and substituent dependencies. Synthesis is rapid being completed within 30 seconds. Yield increases when either reactant is in excess. Yield decreases for alkyl magnified image substituents on the tin in the order methyl > ethyl > t‐butyl > n‐octyl and I > Br > Cl for halide substituents on tin.

Amino derivatives of metals and metalloids : III. Metal amines as reagents for synthesis of organometallics; especially the reactions of aminostannanes with protic species

(Dialkylamino)trialkylstannanes, R 3Sn-NR′ 2, are very reactive reagents. With protic species HA, including hydrogen chloride, water, alcohols, ammonia and primary and secondary amines, diphenylphosphine, diphenylarsine, acetylene and monosubstituted acetylenes, cyclopentadiene and indene, they readily eliminate amine R′ 2NH and afford organotin products of formula R 3Sn-A. Nitriles and nitro-compounds, with α-hydrogen atoms, and acetone are believed to behave similarly in the primary step but side-reactions also are prominent. The great facility of reaction is, in the main, attributed to a weak SnN, bond and it is predicted that these reactions are capable of wide extension not only into the domain of organotin-amino compounds, but also into similar derivatives of other, particularly the more electropositive, metals. This is demonstrated by a synthesis of ferrocene from an iron diethylamide and cyclopentadiene. The amino-derivatives of the elements are very briefly surveyed.

Preparation of cyclopentadienylmetals via cyclopentadienylthallium

1. The synthesis of cyclopentadienyl compounds of Hg, Cr, Fe, Co, and Ni via cyclopentadienylthallium and the halides of the corresponding metals in tetrahydrofuran has been described. 2. The yields of dicyclopentadienyliron, dicyclopentadienylmercury, and dicyclopentadienylcobalt were close to quantiative; in other cases (Cr, Ni) they were about 20%. 3. Both anhydrous ferrous chloride and anhydrous ferric chloride may be used for the synthesis of ferrocene; in the latter case the yield is greater.