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Special Issue "Ferrocene and Ferrocene-Containing Compounds"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organometallic Chemistry".

Deadline for manuscript submissions: closed (1 August 2018).

Special Issue Editor

Prof. Dr. Petr Štěpnička
Website
Guest Editor
Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech Republic
Interests: ferrocene ligands; phosphine ligands; hybrid phosphines; coordination chemistry; catalysis; structure elucidation.

Special Issue Information

Dear Colleagues,

The discovery of ferrocene in the early 1950s brought new life to coordination chemistry and also paved the way to establishing organometallic chemistry as a specific and independent chemical discipline. Since then, numerous studies have focused on the specific bonding principles and reactivity of the ferrocene molecule and possible applications of ferrocene and its derivatives in various fields ranging from the classical areas such as coordination chemistry, organic synthesis and electrochemistry to rapidly developing interdisciplinary fields of materials research, catalysis and biomedicine (and many others).

This Special Issue is intended to highlight the current trends and perspective research focused on ferrocene and ferrocene-containing compounds to demonstrate the enormous width of contemporary ferrocene chemistry and its huge application potential. Researchers studying various aspects of ferrocene chemistry are kindly invited to propose relevant state-of-the-art reviews and, mainly, research papers to be published in this Special Issue of Molecules.

Prof. Dr. Petr Štěpnička
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs), a 50% discount will apply to papers accepted for publication in the Special Issue "Ferrocene and Ferrocene-Containing Compounds". Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • ferrocene
  • synthesis
  • catalysis
  • materials chemistry
  • bioorganometallic chemistry
  • ferrocene ligands
  • organic synthesis
  • coordination chemistry

Published Papers (8 papers)

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Research

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Open AccessArticle
Ferrocene-Containing Sterically Hindered Phosphonium Salts
Molecules 2018, 23(11), 2773; https://doi.org/10.3390/molecules23112773 - 25 Oct 2018
Cited by 6
Abstract
The synthesis and physical properties of the series of the ferrocenyl-containing sterically hindered phosphonium salts based on di(tert-butyl)ferrocenylphosphine is reported. Analysis of voltamogramms of the obtained compounds revealed some correlations between their structures and electrochemical properties. The elongation of the alkyl [...] Read more.
The synthesis and physical properties of the series of the ferrocenyl-containing sterically hindered phosphonium salts based on di(tert-butyl)ferrocenylphosphine is reported. Analysis of voltamogramms of the obtained compounds revealed some correlations between their structures and electrochemical properties. The elongation of the alkyl chain at the P atom as well as replacement of the Br anion by [BF4] shifts the ferrocene/ferrocenium transition of the resulting salts into the positive region. DFT results shows that in the former case, the Br anion destabilizes the corresponding ion pair, making its oxidation easier due to increased highest occupied molecular orbital (HOMO) energy. Increased HOMO energy for ion pairs with the Br ion compared to BF4 are caused by contribution of bromide atomic orbitals to the HOMO. The observed correlations can be used for fine-tuning the properties of the salts making them attractive for applications in multicomponent batteries and capacitors. Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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Open AccessArticle
Ferrocene-Containing Impiridone (ONC201) Hybrids: Synthesis, DFT Modelling, In Vitro Evaluation, and Structure–Activity Relationships
Molecules 2018, 23(9), 2248; https://doi.org/10.3390/molecules23092248 - 03 Sep 2018
Cited by 4
Abstract
Inspired by the well-established clinical evidence about the interplay between apoptotic TRAIL (tumour necrosis factor-related apoptosis-inducing ligand) mechanism and reactive oxygen species (ROS)-mediated oxidative stress, a set of novel ONC201 hybrids containing the impiridone core and one or two differently positioned ferrocenylalkyl groups [...] Read more.
Inspired by the well-established clinical evidence about the interplay between apoptotic TRAIL (tumour necrosis factor-related apoptosis-inducing ligand) mechanism and reactive oxygen species (ROS)-mediated oxidative stress, a set of novel ONC201 hybrids containing the impiridone core and one or two differently positioned ferrocenylalkyl groups were synthesised in our present work. These two types of residues have been implicated in the aforementioned mechanisms associated with cytotoxic activity. A straightforward, primary amine-based synthetic approach was used allowing the introduction of a variety of N-substituents into the two opposite regions of the heterocyclic skeleton. Reference model compounds with benzyl and halogenated benzyl groups were also synthesised and tested. The in vitro assays of the novel impiridones on five malignant cell lines disclosed characteristic structure-activity relationship (SAR) featuring significant substituent-dependent activity and cell-selectivity. A possible contribution of ROS-mechanism to the cytotoxicity of the novel metallocenes was suggested by density functional theory (DFT)studies on simplified models. Accordingly, unlike the mono-ferrocenylalkyl-substituted products, the compounds containing two ferrocenylalkyl substituents in the opposite regions of the impiridone core display a much more pronounced long-term cytotoxic effect against A-2058 cell line than do the organic impiridones including ONC201 and ONC212. Furthermore, the prepared bis-metallocene derivatives also present substantial activity against COLO-205- and EBC-1 cell lines. Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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Open AccessArticle
Probing the Anticancer Action of Novel Ferrocene Analogues of MNK Inhibitors
Molecules 2018, 23(9), 2126; https://doi.org/10.3390/molecules23092126 - 23 Aug 2018
Cited by 8
Abstract
Two novel ferrocene-containing compounds based upon a known MNK1/2 kinase (MAPK-interacting kinase) inhibitor have been synthesized. The compounds were designed to use the unique shape of ferrocene to exploit a large hydrophobic pocket in MNK1/2 that is only partially occupied by the original [...] Read more.
Two novel ferrocene-containing compounds based upon a known MNK1/2 kinase (MAPK-interacting kinase) inhibitor have been synthesized. The compounds were designed to use the unique shape of ferrocene to exploit a large hydrophobic pocket in MNK1/2 that is only partially occupied by the original compound. Screening of the ferrocene analogues showed that both exhibited potent anticancer effects in several breast cancer and AML (acute myeloid leukemia) cell lines, despite a loss of MNK potency. The most potent ferrocene-based compound 5 was further analysed in vitro in MDA-MB-231 (triple negative breast cancer cells). Dose–response curves of compound 5 for 2D assay and 3D assay generated IC50 values (half maximal inhibitory concentration) of 0.55 µM and 1.25 µM, respectively. Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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Open AccessArticle
Synthesis and Coordination Behavior of a Flexible Bis(phosphinoferrocene) Ligand
Molecules 2018, 23(8), 2054; https://doi.org/10.3390/molecules23082054 - 16 Aug 2018
Cited by 1
Abstract
A symmetrical flexible bis(phosphinoferrocene) derivative, viz. bis[1′-(diphenylphosphino)ferrocenyl]methane (1), was prepared and studied as a ligand in Pd(II) and Au(I) complexes. The reactions of 1 with [PdCl2(cod)] (cod = cycloocta-1,5-diene) and [Pd(μ-Cl)(LNC)]2 (LNC = [2-(dimethylamino-κN [...] Read more.
A symmetrical flexible bis(phosphinoferrocene) derivative, viz. bis[1′-(diphenylphosphino)ferrocenyl]methane (1), was prepared and studied as a ligand in Pd(II) and Au(I) complexes. The reactions of 1 with [PdCl2(cod)] (cod = cycloocta-1,5-diene) and [Pd(μ-Cl)(LNC)]2 (LNC = [2-(dimethylamino-κN)methyl]phenyl-κC1) produced bis(phosphine) complex trans-[PdCl2(12P,P′)] (4), wherein the ligand spans trans positions in the square-planar coordination sphere of Pd(II) and the tetranuclear, P,P-bridged complex [(μ(P,P′)-1){PdCl(LNC)}2] (5), respectively. In reactions with the Au(I) precursors [AuCl(tht)] and [Au(tht)2][SbF6] (tht = tetrahydrothiophene), ligand 1 gave rise to tetranuclear Au2Fe2 complex [(μ(P,P′)-1)(AuCl)2] (6) and to symmetrical macrocyclic tetramer [Au4(μ(P,P′)-1)4][SbF6]4 (7). All compounds were characterized by spectroscopic methods. In addition, the structures of compound 1, its synthetic precursor bis[1′-(diphenylphosphino)ferrocenyl]methanone (3), and all aforementioned Pd(II) and Au(I) complexes were determined by single-crystal X-ray diffraction analysis (some in solvated form). Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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Open AccessArticle
Synthesis and Light-Induced Actuation of Photo-Labile 2-Pyridyl-1,2,3-Triazole Ru(bis-bipyridyl) Appended Ferrocene Rotors
Molecules 2018, 23(8), 2037; https://doi.org/10.3390/molecules23082037 - 14 Aug 2018
Cited by 2
Abstract
To realise useful control over molecular motion in the future an extensive toolbox of both actionable molecules and stimuli-responsive units must be developed. Previously, our laboratory has reported 1,1′-disubstituted ferrocene (Fc) rotor units which assume a contracted/π-stacked conformation until complexation of cationic metal [...] Read more.
To realise useful control over molecular motion in the future an extensive toolbox of both actionable molecules and stimuli-responsive units must be developed. Previously, our laboratory has reported 1,1′-disubstituted ferrocene (Fc) rotor units which assume a contracted/π-stacked conformation until complexation of cationic metal ions causes rotation about the Ferrocene (Fc) molecular ‘ball-bearing’. Herein, we explore the potential of using the photochemical ejection of [Ru(2,2′-bipyridyl)2]2+ units as a stimulus for the rotational contraction of new ferrocene rotor units. Fc rotors with both ‘regular’ and ‘inverse’ 2-pyridyl-1,2,3-triazole binding pockets and their corresponding [Ru(2,2′-bipyridyl)2]2+ complexes were synthesised. The rotors and complexes were characterised using nuclear magnetic resonance (NMR) and ultraviolet (UV)-visible spectroscopies, Electro-Spray Ionisation Mass Spectrometry (ESI–MS), and electrochemistry. The 1,1′-disubstituted Fc ligands were shown to π-stack both in solution and solid state. Density Functional Theory (DFT) calculations (CAM-B3LYP/6-31G(d)) support the notion that complexation to [Ru(2,2′-bipyridyl)2]2+ caused a rotation from the syn- to the anti-conformation. Upon photo-irradiation with UV light (254 nm), photo-ejection of the [Ru(2,2′-bipyridyl)2(CH3CN)2]2+ units in acetonitrile was observed. The re-complexation of the [Ru(2,2′-bipyridyl)2]2+ units could be achieved using acetone as the reaction solvent. However, the process was exceedingly slowly. Additionally, the Fc ligands slowly decomposed when exposed to UV irradiation meaning that only one extension and contraction cycle could be completed. Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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Open AccessArticle
Trapping para-Quinone Methide Intermediates with Ferrocene: Synthesis and Preliminary Biological Evaluation of New Phenol-Ferrocene Conjugates
Molecules 2018, 23(6), 1335; https://doi.org/10.3390/molecules23061335 - 01 Jun 2018
Cited by 2
Abstract
The reaction of para-hydroxybenzyl alcohols with ferrocene in the presence of a catalytic amount of InCl3 provided ferrocenyl phenol derivatives, an interesting class of organometallic compounds with potential applications in medicinal chemistry. This transformation exhibited a reasonable substrate scope delivering the [...] Read more.
The reaction of para-hydroxybenzyl alcohols with ferrocene in the presence of a catalytic amount of InCl3 provided ferrocenyl phenol derivatives, an interesting class of organometallic compounds with potential applications in medicinal chemistry. This transformation exhibited a reasonable substrate scope delivering the desired products in synthetically useful yields. Evidence of involvement of a para-quinone methide intermediate in this coupling process was also provided. Preliminary biological evaluation demonstrated that some of the ferrocene derivatives available by this methodology exhibit significant cytotoxicity against several cancer cell lines with IC50 values within the range of 1.07–4.89 μM. Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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Open AccessArticle
Enantiomerically Enriched 1,2-P,N-Bidentate Ferrocenyl Ligands for 1,3-Dipolar Cycloaddition and Transfer Hydrogenation Reactions
Molecules 2018, 23(6), 1311; https://doi.org/10.3390/molecules23061311 - 30 May 2018
Cited by 2
Abstract
Novel complexes of 1,2-P,N-bidentate ferrocenyl ligands with AgOAc or with [RuCl2(PPh3)3] as catalysts have been studied in asymmetric synthesis. The catalytic activity of these systems have been studied in [3+2]-cycloaddition of azomethine ylides with olefins and the asymmetric transfer hydrogenation of ketones. Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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Review

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Open AccessReview
Ferrocenes as Building Blocks in Molecular Rectifiers and Diodes
Molecules 2018, 23(7), 1551; https://doi.org/10.3390/molecules23071551 - 27 Jun 2018
Abstract
Ferrocenes have recently been reported as components of a number of molecular circuits. This short review covers reports of ferrocenes in molecular rectifiers and diodes which have appeared in the last 10 years. Full article
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
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