1273-86-5Relevant articles and documents
Synthesis and electronic properties of ferrocene-containing organic dyads
Watanabe, Motonori,Chang, Yuan Jay,Chou, Po-Ting,Staykov, Aleksandar,Shibahara, Masahiko,Sako, Katsuya,Ishihara, Tatsumi,Chow, Tahsin J.
, p. 1548 - 1551 (2015)
Novel ferrocene-oligothiophenylene-cyanoacrylic acid in the form of donor-spacer-acceptor dyads was synthesized. The compound with a single unit of thiophenylene showed the lowest energy transition in neutral state. For radical cations, the lowest energy transition appears red-shifted along with the increased number of thiophenylene units. These results suggested that the electronic structure of radical cations is significantly different from that of neutral molecules.
Click-chemistry approach to synthesis of functionalized isatin-ferrocenes and their biological evaluation against the human pathogen Trichomonas vaginalis
Singh, Amandeep,Zhang, David,Tam, Christina C.,Cheng, Luisa W.,Land, Kirkwood M.,Kumar, Vipan
, p. 1 - 4 (2019)
Copper-promoted azide-alkyne cycloadditions were attempted to synthesize a series of variedly functionalized 1H-1,2,3-triazole-linked isatin-ferrocene, ferrocenylmethoxy-isatin and isatin-ferrocenyl-chalcone conjugates. The synthesized scaffolds were assayed for their inhibitory activity against T. vaginalis as well as several common normal human flora bacteria. The observed inhibitory activities against T. vaginalis and undetectable inhibition of microflora bacteria suggest that these compounds may be specific against trichomonad protozoa and could serve as a new scaffold for synthesis of novel compounds against this important human pathogen.
Formylation of a metathesis-derived: Ansa [4]-ferrocene: A simple route to anticancer organometallics
Bretner, Maria,Buchowicz, W?odzimierz,Kamiński, Rados?aw,Koszytkowska-Stawińska, Mariola,Mazur, Maria,Mrozowicz, Micha?,Ochal, Zbigniew,Wińska, Patrycja
, p. 11504 - 11511 (2020)
Formylation of ansa[4]-ferrocene, obtained through the ruthenium-catalysed olefin metathesis, yields two separable, planar chiral 1,3-and 1,2-ansa-ferrocene aldehydes. Single-crystal X-ray structure analysis reveals that both regioisomers crystallize with spontaneous resolution of the racemate in the chiral P212121 space group with one molecule in the asymmetric unit. The major 1,3-isomer was further transformed into a conjugate with 1,2,3-triazole and uracil using click chemistry as the key synthetic step. This inorganic-organic hybrid displays anticancer activity (MCF-7, A549, MDA-MB-231 cell lines) with EC50 values comparable to those for cisplatin.
Bublitz, D. E.,Harris, G. H.
, p. 404 - 408 (1965)
Electrocatalytic hydrocarbon hydroxylation by ethylbenzene dehydrogenase from Aromatoleum aromaticum
Kalimuthu, Palraj,Heider, Johann,Knack, Daniel,Bernhardt, Paul V.
, p. 3456 - 3463 (2015)
We report the electrocatalytic activity of ethylbenzene dehydrogenase (EBDH) from the β-proteobacterium Aromatoleum aromaticum. EBDH is a complex 155 kDa heterotrimeric molybdenum/iron-sulfur/heme protein which catalyzes the enantioselective hydroxylation of nonactivated ethylbenzene to (S)-1-phenylethanol without molecular oxygen as cosubstrate. Furthermore, it oxidizes a wide range of other alkyl-substituted aromatic and heterocyclic compounds to their secondary alcohols. Hydroxymethylferrocenium (FM) is used as an artificial electron acceptor for EBDH in an electrochemically driven catalytic system. Electrocatalytic activity of EBDH is demonstrated with both its native substrate ethylbenzene and the related substrate p-ethylphenol. The catalytic system has been modeled by electrochemical simulation across a range of sweep rates and concentrations of each substrate, which provides new insights into the kinetics of the EBDH catalytic mechanism.
Physicochemical properties of nitrogen-doped carbon nanotubes from metallocenes and ferrocenyl imidazolium compounds
Labulo, Ayomide H.,Ngidi, Nonjabulo P.D.,Omondi, Bernard,Nyamori, Vincent O.
, p. 66 - 75 (2018)
Shaped carbon nanomaterials (SCNMs) were synthesized via the chemical vapour deposition (CVD) technique by using typical metallocenes (ferrocene, nickelocene, cobaltocene, and ruthenocene), and more interestingly, by use of novel ferrocenyl imidazolium derivatives, containing -Cl (FcImCl), -NO2 (FcImNO2) and -CH3 (FcImCH3) substituents as catalysts. Acetonitrile was applied both as a carbon and nitrogen source at temperatures 800–900 °C. The SCNMs, namely, carbon nanotubes (CNTs), carbon spheres (CS), carbon fibres (CF) and amorphous carbons (ACs) were obtained in varying ratios depending on the catalyst and carbon sources. The ferrocenyl imidazolium catalysts produced nitrogen-doped CNTs (N-CNTs) with bamboo-like structures. The yields of various reactions were temperature-dependent, with the highest amount of N-CNTs obtained at 850 °C. In all samples, the composition was mainly of CS and N-CNTs except for nickelocene at 800 °C that gave CFs as a “minor” product. Ferrocene and nickelocene in acetonitrile produced well-aligned N-CNTs while cobaltocene and ruthenocene gave 'spaghetti-like’ structures. In the case of ferrocenyl imidazolium catalyst, a coiled N-CNTs morphology was produced from FcImCl catalyst. Also, higher percentage of N-CNTs with traces of CS were obtained from the FcImCl and FcImCH3 catalysts in acetonitrile at 850 °C, while higher percentage of CS and AC were obtained for FcImNO2 catalyst. In all the catalysts, the use of acetonitrile promoted nitrogen-doping (samples with more disordered and with smaller outer-diameters). Thus, this study demonstrates that the synthesis of N-CNTs from nitrogen-containing ferrocenyl imidazolium compounds as catalyst sources, provided higher percentage of N-CNTs which can be suitable for various application.
MOESSBAUER STUDIES ON FERROCENE COMPLEXES. III. STRUCTURE OF FERROCENYL CARBENIUM IONS
Neshvad, G.,Roberts, R.M.G.,Silver, J.
, p. 85 - 92 (1981)
Moessbauer and NMR spectra are reported for ferrocenyl (Fc) carbenium ions, FcCH2+ (III+) and FcC+Me2 (II+) in frozen acidic media. 1H-NMR spectra showed no evidence of Fe-H bonded species.Moessbauer parameters
Activation by Oxidation: Ferrocene-Functionalized Ru(II)-Arene Complexes with Anticancer, Antibacterial, and Antioxidant Properties
Mu, Changhua,Prosser, Kathleen E.,Harrypersad, Shane,Macneil, Gregory A.,Panchmatia, Rikesh,Thompson, John R.,Sinha, Soumalya,Warren, Jeffrey J.,Walsby, Charles J.
, p. 15247 - 15261 (2018)
Organometallic Ru(II)-cymene complexes linked to ferrocene (Fc) via nitrogen heterocycles have been synthesized and studied as cytotoxic agents. These compounds are analogues of Ru(II)-arene piano-stool anticancer complexes such as RAPTA-C. The Ru center was coordinated by pyridine, imidazole, and piperidine with 0-, 1-, or 2-carbon bridges to Fc to give six bimetallic, dinuclear compounds, and the properties of these complexes were compared with their non-Fc-functionalized parent compounds. Crystal structures for five of the compounds, their Ru-cymene parent compounds, and an unusual trinuclear compound were determined. Cyclic voltammetry was used to determine the formal MIII/II potentials of each metal center of the Ru-cymene-Fc complexes, with distinct one-electron waves observed in each case. The Fc-functionalized complexes were found to exhibit good cytotoxicity against HT29 human colon adenocarcinoma cells, whereas the parent compounds were inactive. Similarly, antibacterial activity from the Ru-cymene-Fc compounds was observed against Bacillus subtilis, but not from the unfunctionalized complexes. In both cases, the IC50 values correlated quantitatively with the Fc+/0 reduction potentials. This is consistent with more facile oxidation to give ferrocenium, and subsequent generation of toxic reactive oxygen species, leading to greater cytotoxicity. The antioxidant properties of the complexes were quantified by a 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. EC50 values indicate that linking of the Ru and Fc centers promotes antioxidant activity.
A Stable Primary Phosphane Oxide and Its Heavier Congeners
Horky, Filip,Císa?ová, Ivana,?těpni?ka, Petr
, p. 1282 - 1285 (2021)
(Ferrocenylmethyl)phosphane (1) oxidation with hydrogen peroxide, elemental sulfur and grey selenium produced (ferrocenylmethyl)phosphane oxide 1O, sulfide 1S and selenide 1Se, respectively, as the first isolable primary phosphane chalcogenides lacking steric protection. At elevated temperatures, compound 1O disproportionated into 1 and (ferrocenylmethyl)phosphinic acid. In reactions with [(η6-mes)RuCl2]2, 1O underwent tautomerization into a phosphane complex [(η6-mes)RuCl2{FcCH2PH(OH)-κP}], whereas 1S and 1Se lost their P-bound chalcogen atoms, giving rise to the phosphane complex [(η6-mes)RuCl2(FcCH2PH2-κP)] (Fc=ferrocenyl, mes=mesitylene). No tautomerization was observed in the reaction of 1O with B(C6F5)3, which instead produced a Lewis pair FcCH2P(O)H2-B(C6F5)3. Phosphane oxide 1O added to C=O bonds of aldehydes and ketones and even to cumulenes PhNCE (E=O and S). However, both PH hydrogens were only employed in the reactions with aldehydes and cyanates.
Light-Triggered Metal Coordination Dynamics in Photoswitchable Dithienylethene-Ferrocene System
Adarsh, Nayarassery N.,Karmakar, Manisha,Mondal, Bijan,Pal, Adwitiya,Thakur, Arunabha
supporting information, p. 6086 - 6098 (2021/05/06)
The C2-symmetric photochromic molecule 3, containing dithienylethene (DTE) and ferrocene units connected by an alkyne bridge, represents a unique probe where a metal (Hg2+) binds with the central DTE moiety. Both photoisomerized states of 3 (open, 3o; closed, 3c) are found to interact with Hg2+ ion by the S atoms of the DTE core; however, the binding constants (from a UV-vis study) and DFT calculations suggest that the open isomer (3o) binds with the metal ion more strongly than that of the closed isomer (3c). Notably, the course of metal binding does not perturb the inherent photoisomerization properties of the DTE core and the photoswitchability persists even in the metal-coordinated form of 3, however, with a comparatively slower rate. The quantum yields for photocyclization (φo→c) and photocycloreversion (φc→o) in the free form are 0.56 and 0.007, respectively, whereas the photocyclization quantum yield in the Hg2+ complexed species is 0.068, 8.2 times lower than the photocyclization quantum yield (φo→c) of free 3o. Thus, the rate of photoisomerization can be modulated by a suitable metal coordination to the DTE core. The dynamics of photoswitchability in the metal-coordinated form of DTE has been explored by experimental means (UV-vis and electrochemical studies) as well as quantum chemical calculations.
Azide-alkyne cycloaddition en route to ferrocenyl-methoxy-methyl-isatin-conjugates: Synthesis, anti-breast cancer activities and molecular docking studies
Rani, Anu,Singh, Gurjot Inder,Kaur, Ramandeep,Palma, Gabriella,Perumal, Shanen,Kaur, Mandeep,Ebenezer, Oluwakemi,Awolade, Paul,Singh, Parvesh,Kumar, Vipan
, (2019/12/23)
A series of 1H-1,2,3-triazole linked Ferrocenyl-methoxy-methyl-Isatin conjugates was synthesized and assayed for their anti-proliferative activities against estrogen-responsive as well as estrogen non-responsive cell lines. The non-cytotoxic conjugate 7l, with an optimum combination of octyl chain as spacer and methyl-substituent at the C-5 position of isatin, proved to be a promising hit with an IC50 value of 14.62 μM against MCF-7 and 79.63 μM against MDA-MB-231 cells, respectively. The observed anti-proliferative activities of active conjugates were further corroborated via docking studies carried out on estrogen receptor subtypes α and β.
