- Reuseable monolithic nanoporous graphite-supported nanocatalysts (Fe, Au, Pt, Pd, Ni, and Rh) from pyrolysis and galvanic transmetalation of ferrocene-based polyamide aerogels
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Polyamide aerogels with ferrocene as a monomer repeat unit were prepared in one step from ferrocene dicarboxylic acid and tris(4-isocyanatophenyl)methane. Pyrolysis at ≥800 °C yielded nanoporous carbons doped throughout with crystallites of α-Fe (about 50 nm in diameter), which in turn were shrouded in graphitic ribbons (a path akin to galvanic corrosion, whereas graphitic ribbons separated anodes (α-Fe particles) from cathodes (defects along the ribbons). The new metallic phases formed clusters of smaller crystallites (10-20 nm in diameter) on the graphitic ribbons, leaving behind empty cage-like formations previously occupied by the Fe(0) nanoparticles. All metal-doped carbons were monolithic and over 85% porous. Catalytic activity was demonstrated with the oxidation of benzyl alcohol to benzaldehyde catalyzed with carbon-supported Au or Pt, the reduction of nitrobenzene by hydrazine to aniline catalyzed with carbon-supported Fe, and two Heck coupling reactions of iodobenzene with styrene or butyl acrylate, catalyzed with carbon-supported Pd. The distinguishing feature of those catalysts was that they could be just picked up, for example, with a pair of tweezers, and redeployed in a new reaction mixture immediately, thus bypassing less efficient recovery processes like filtration.
- Saeed, Adnan M.,Wisner, Clarissa A.,Donthula, Suraj,Majedi Far, Hojat,Sotiriou-Leventis, Chariklia,Leventis, Nicholas
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- Synthesis of new ferrocene derivatives with a 4,5-dichloroisothiazole fragment
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Conjugates of ferrocene and 4,5-dichloroisothiazole were synthesized, where the ferrocene and isothiazole moieties are linked through various structural fragments. The acylation of ferrocene with 4,5- dichloroisothiazole-3-carbonyl chloride gave (4,5-dichloroisothiazol-3-yl) ferrocenyl ketone; the acylation of aminomethylferrocene furnished the corresponding amide. The esterification of ferrocene-1,1′-dicarboxylic acid with 4,5-dichloroisothiazol-3-yl-methanol resulted in the formation of the corresponding ester. The condensation of 1,1′-diacetylferrocene with 4,5-dichloroisothiazole-3-carbaldehyde afforded ferrocenophane containing 4,5-dichloroisothiazole moieties.
- Kletskov,Kolesnik,Dikusar,Zhukovskaya,Potkin
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- Use of Boolean and fuzzy logics in lactose glycocluster research
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Fuzzy logic systems can be exploited for defining the degrees of true or false binding between calcium mediated multivalent lactose and peanut agglutinin lectin, which are difficult to define with Boolean logic.
- Bavireddi, Harikrishna,Bharate, Priya,Kikkeri, Raghavendra
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- Large-scale preparation of 1,1′-ferrocenedicarboxylic acid, a key compound for the synthesis of 1,1′-disubstituted ferrocene derivatives
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Efficient and simple methods for the large-scale preparation of 1,1′-ferrocenedicarboxylic acid, fc(COOH)2, involving the sodium salts of cyclopentadienecarboxylic methyl and ethyl esters, Na(C 5H4COOR) (R = Me, Et), are presented. With fc(COOH) 2 at hand, the syntheses of various 1,1′-disubstituted compounds of the type fcX2 (X = CH2OH, COCl, CON 3, NCO, NHCOOMe, NHBoc, NH2) were optimized and scaled up. The X-ray crystal structures of fc(COOEt)2, fc(NCO) 2·1/2C6H6, and fc(NHCOOMe)2·MeOH are reported.
- Petrov, Alex R.,Jess, Kristof,Freytag, Matthias,Jones, Peter G.,Tamm, Matthias
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- Ferrocene Macrocyclic Schiff Base Complex: Synthesis, Structure and Recognition Properties for Dual Hg2+ and Cu2+
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A probe based on ferrocene structure has been designed, synthesized and elucidated from the single crystal X-ray method. It demonstrated fluorescence response to Hg2+ and Cu2+ in CH3OH. The results indicated that the title complex could be applied in the multianalyte detection. Binding ability of receptor 3 in CH3OH was tested for various cations (Fe3+, Co2+, Cu2+, Zn2+, Cd2+, Hg2+, Pb2+, and Ba2+ in water). The computed binding constants for Hg2+ and Cu2+ indicated a distinct absorbance shift. The receptor is an attractive array due to its distinct absorbance shift profile in a semi-aqueous phase, making it applicable in biology, environmental sciences and material chemistry.
- Liu, Xiaoju,Xiang, Yulin,Ma, Xiangrong,Ren, Guoyu,Gao, Liguo
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- Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells
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Malaria and cancer cause the death of millions of people every year. To combat these two diseases, it is important that new pharmaceutically active compounds have the ability to overcome multidrug resistance in cancer and Plasmodium falciparum strains. In search of effective anti-cancer and anti-malaria hybrids that possess improved properties compared to their parent compounds, a series of novel 1,2,4-trioxane-based hybrids incorporating egonol and/or ferrocene fragments were synthesized and tested in vitro against P. falciparum strains, CCRF-CEM cells and the multidrug-resistant P-glycoprotein-over-expressing CEM/ADR5000 cells. The most active compounds against P. falciparum strains were artesunic acid homodimers 12 and 13 (IC 50 of 0.32 and 0.30 nM, respectively), whereas novel hybrids 7 (1,2,4-trioxane-ferrocene-egonol), 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol) showed a remarkable cytotoxicity toward CCRF-CEM cells (IC50 of 0.07, 0.25 and 0.18 μM, respectively). A cooperative and synergistic effect of the three moieties 1,2,4-trioxane, ferrocene and egonol in hybrid molecule 7 is significant and is obviously stronger than in hybrids 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol), which comprises of only two of the three considered parent compounds. Interestingly, hybrid 9 containing a 1,2,4-trioxane and a ferrocene fragment has shown to be the most effective among the studied hybrids against the tested multidrug-resistant leukemia CEM/ADR5000 cells (IC50 of 0.57 μM) and possesses a degree of cross-resistance of 2.34.
- Reiter, Christoph,?apci Karag?z, Aysun,Fr?hlich, Tony,Klein, Volker,Zeino, Maen,Viertel, Katrin,Held, Jana,Mordmüller, Benjamin,Emirda? ?ztürk, Safiye,Anil, Hüseyin,Efferth, Thomas,Tsogoeva, Svetlana B.
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- New efficient artemisinin derived agents against human leukemia cells, human cytomegalovirus and Plasmodium falciparum: 2nd generation 1,2,4-trioxane-ferrocene hybrids
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In our ongoing search for highly active hybrid molecules exceeding their parent compounds in anticancer, antimalaria as well as antiviral activity and being an alternative to the standard drugs, we present the synthesis and biological investigations of 2nd generation 1,2,4-trioxane-ferrocene hybrids. In vitro tests against the CCRF-CEM leukemia cell line revealed di-1,2,4-trioxane-ferrocene hybrid 7 as the most active compound (IC50 of 0.01 μM). Regarding the activity against the multidrug resistant subline CEM/ADR5000, 1,2,4-trioxane-ferrocene hybrid 5 showed a remarkable activity (IC50 of 0.53 μM). Contrary to the antimalaria activity of hybrids 4-8 against Plasmodium falciparum 3D7 strain with slightly higher IC50 values (between 7.2 and 30.2 nM) than that of their parent compound DHA, hybrids 5-7 possessed very promising activity (IC50 values lower than 0.5 μM) against human cytomegalovirus (HCMV). The application of 1,2,4-trioxane-ferrocene hybrids against HCMV is unprecedented and demonstrated here for the first time.
- Reiter, Christoph,Fr?hlich, Tony,Zeino, Maen,Marschall, Manfred,Bahsi, Hanife,Leidenberger, Maria,Friedrich, Oliver,Kappes, Barbara,Hampel, Frank,Efferth, Thomas,Tsogoeva, Svetlana B.
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- Synthesis, crystal structure and properties of two novel ferrocenophane compounds
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The title compounds were synthesized via click reaction. They were characterized by IR, 1H-NMR, elemental analysis, UV, fluorescence in solution were also applied to characterise their photophysical characterization and single-crystal X-ray diffraction analysis. 1,1′-Ferrocene-dicarboxyl-{[(3-methylphenyl)-imino]di-2,1-ethanediyl} 1 (C23H23FeNO4) crystallizes in the monoclinic system, with a = 7.4261(13), b = 29.911(5), c = 9.8426(13) ?, α = 90°, β = 118.251(10)°, γ = 90°, V = 1925.8(5) ?3, 1,1′-Ferrocene-dicarboxyl-{[(2-methylphenyl)-imino]di-2,1-ethanediyl} 2 (C23H23FeNO4) crystallizes in the monoclinic system, with a = 15.4000 (15), b =7.9007 (8), c = 16.0776 (15) ?, α = 90°, β = 94.266 (2)°, γ = 90°, V = 1950.8 (3)? 3, Both 1 and 2 form 3D net structures, which are further linked to form 3D supramolecular net structures via intermolecular C?H···O, C?H···π and C?H···C stacking interactions, respectively. Fluorescent and UV-vis absorption spectra were also investigated.
- Liu, Xiaoju,Gao, Liguo,Ren, Guoyu,Ma, Yajun,Li, Jian,Yan, Biao
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- A functionalized Ag2S molecular architecture: Facile assembly of the atomically precise ferrocene-decorated nanocluster [Ag74S19(dppp)6(fc(C{O}OCH2CH2S)2)18]
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A ferrocene-based dithiol 1,1′-[fc(C{O}OCH2CH2SH)2] has been prepared and treated with a AgI salt to form the stable dithiolate compound [fc(C{O}OCH2CH2SAg)2]n (fc=[Fe
- Liu, Yiyi,Khalili Najafabadi, Bahareh,Azizpoor Fard, Mahmood,Corrigan, John F.
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- Synthesis of ferrocenylated-aminopyridines and ferrocenylated-aminothiazoles and their anti-migration and burning rate catalytic properties
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For overcoming the migration problems of ferrocene (Fc)-based burning rate catalysts (BRCs) as well as for enhancing burning rate (BR) of ammonium perchlorate (AP)-based propellants, ferrocenylated-amino pyridines (AP-Fcs) and ferrocenylated-amino thiazol
- Fahad, Shah,Khan, Amin,Lemenovskiy, Dmitry A.,Naveed, Kaleem-ur-Rehman,Nazir, Ahsan,Usman, Muhammad,Wang, Li,Yu, Haojie,Zarubin, Dmitry N.,Zhizhko, Pavel A.
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- Structure-Dependent Guest Recognition with Flexible Ferrocene-Based Aromatic Oligoamide β-Sheet Mimics
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A series of aromatic oligoamides incorporating an inherently flexible ferrocene dicarboxylic acid unit was synthesized. Solid state, solution, and computational studies on these systems indicated that the aromatic strands can adopt a syn parallel stacked conformation. This results in modular β-sheet-like molecular clefts that display structure-dependent recognition of small polar molecules. NMR and theoretical studies of the host–guest interaction support an in cleft binding mode and allowed the selectivity of the oligomers to be rationalized on the basis of minor changes in functional-group presentation on the edge of the aromatic strands.
- Liu, Ya-Zhou,Wang, Hu,Chan, Chieh-Kai,Mu, Xiao,Robeyns, Koen,Wang, Cheng-Chung,Singleton, Michael L.
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- Ferrocenes as potential chemotherapeutic drugs: Synthesis, cytotoxic activity, reactive oxygen species production and micronucleus assay
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Three new ferrocene complexes were synthesized with 4-(1H-pyrrol-1-yl)phenol group appended to one of the Cp ring. These are: 1,1′-4-(1H-pyrrol-1-yl)phenyl ferrocenedicarboxylate, ('Fc-(CO2-Ph-4-Py)2'), 1,4-(1H-pyrrol-1-yl)phenyl, 1′-carboxyl ferrocenecarboxylate ('Fc-(CO2-Ph-4-Py)CO2H') and 4-(1H-pyrrol-1-yl)phenyl ferroceneacetylate ('Fc-CH2CO2-Ph-4-Py'). The new species were characterized by standard analytical methods. Cyclic voltammetry experiments showed that Fc-CH2CO2-Ph-4-Py has redox potential very similar to the Fc/Fc+ redox couple whereas Fc-(CO2-Ph-4-Py)2 and Fc-(CO2-Ph-4-Py)CO2H have redox potentials of over 400 mV higher than Fc/Fc+ redox couple. The in vitro studies on Fc-(CO2-Ph-4-Py)2 and Fc-(CO2-Ph-4-Py)CO2H revealed that these two compounds have moderate anti-proliferative activity on MCF-7 breast cancer cell line. In contrast Fc-CH2CO2-Ph-4-Py which displayed low anti-proliferative activity. In the HT-29 colon cancer cell line, the new species showed low anti-proliferative activity. Cytokinesis-block micronucleus assay (CBMN) was performed on these ferrocenes and it was determined they induce micronucleus formation on binucleated cells and moderate genotoxic effects on the MCF-7 breast cancer cell line. There is a correlation between the IC50 values of the ferrocenes and the amount of micronucleus formation activity on binucleated cells and the reactive oxygen species (ROS) production on MCF-7 cell line.
- Pérez, Wanda I.,Soto, Yarelys,Ortíz, Carmen,Matta, Jaime,Meléndez, Enrique
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- 1,9-Dicarbonyl-2,8-dioxo-butyne-ester Ferrocenophane: Synthesis, Structure and Recognition Properties for Co2+ and Cu2+ Ions
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An efficient highly diluted synthetic approach to the synthesis of 1,9-dicarbonyl-2,8-dioxo-butyne ester ferrocenophane (L) has been developed. The title compound was characterized by IR, UV, FL, 1H NMR, spectroscopies, elemental analysis and so on. Furth
- Liu, Xiaoju,Ren, Guoyu,Ma, Xiangrong,Xiang, Yulin,Gao, Liguo,Ma, Xiaoyan
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- A nanostructured Fc(COCH3)2 film prepared using silica monolayer colloidal crystal templates and its electrochromic properties
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Since oxidation and reduction reactions mainly take place on surfaces, enlarging the specific surface of redox materials is the key to achieving excellent electrochemical performance. In this work, by using silica monolayer colloidal crystal templates (MCCTs), a nanostructured Fc(COCH3)2 film is prepared successfully, and such a nanostructure could exhibit the following unique electrochemical properties: the MCCTs could impede the aggregation tendency of Fc(COCH3)2 and possess high electrochemical activity; Fc(COCH3)2 enlarges the contact area and offers more active sites and faster electronic transmission channels. The structure, optical and electrochemical properties of the nanostructured Fc(COCH3)2 were tested and then compared with those of compact Fc(COCH3)2 films to evaluate the role of the nanoarchitecture. The unique structure design of the Fc(COCH3)2 film enables outstanding performance, showing a large transmittance change (ΔT) of 37% at 550 nm when switched between 0.5 V and -2.5 V, which is approximately ninefold higher than that of the compact Fc(COCH3)2 film (approximately 4%). Response times of coloration and bleaching are found to be only 16.15 s and 5.56 s. Furthermore, the nanostructured Fc(COCH3)2 film shows much better cycling stability than the compact one. The results indicate that the nanostructure could significantly improve the electrochemical performance of the Fc(COCH3)2 film due to the increase in electrochemical active sites and the enhancement of the D-to-A redox switch of ferrocene.
- Hua, Chunxia,Dou, Shuliang,Xu, Hongbo,Hou, Shuai,Zhang, Hangchuan,Zhang, Panpan,Gan, Yang,Zhao, Jiupeng,Li, Yao
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- Synthesis and Cation-Complexing Ability of Ferrocene or Ruthenocene Functionalized Crown Ethers Possessing 2,6-Pyridino Moieties
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Keto crown ethers that contain ferrocene or ruthenocene and 2,6-disubstituted pyridine unit as part of the major ring have been reported.These keto crown ethers were synthesized by a reaction of 1,1'-metallocenedicarbonyl dichloride (ferrocene or ruthenocene) with 2,6-bispyridine by using a high-dilution method.Their complexing ability with metal cations was measured by a solvent-extraction method, and was found to be poor with alkali metal cations but excellent with Ag(1+), In(3+), and Zr(4+) cations.
- Izumi, Takeo,Murakami, Satoshi,Kasahara, Akira
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- Synthesis and characterization of a redox-active ion channel supporting cation flux in lipid bilayers
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The synthesis, cation binding and transmembrane conductive properties of a novel synthetic ion channel containing a redox-active ferrocene unit are described. Fluorescence spectroscopy was used to demonstrate that the channel supports multiple ion coordin
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- Porphyrin-ferrocene conjugates for photodynamic and chemodynamic therapy
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Chemodynamic therapy can convert endogenous hydrogen peroxide (H2O2) at tumor localization into the toxic hydroxyl radical (OH) destroying tumor cells. Photodynamic therapy as a noninvasive method utilizes photosensitizers (PSs) to c
- Lei, Zhitao,Zhang, Xiaoyu,Zheng, Xiaohua,Liu, Shi,Xie, Zhigang
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- Synthesis and characterization of novel ferrocenyl heterocyclic compounds
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An efficient synthetic approach to the synthesis of ferrocenyl heterocyclic derivatives in dilute solutions has been developed. The new compounds were characterised by means of IR, UV, and 1H NMR, spectroscopy and elemental analysis. The structure of complex I was studied by X-ray single-crystal diffraction. The synthesized compounds have a potential of new enzyme models and molecular recognition hosts.
- Liu, Xiaoju,Ren, Guoyu,Ma, Xiangruo,Yan, Long,Jiao, Yurong,Ma, Yajun,Yang, Bingqin
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- Synthesis and X-ray crystal structure of two novel ester ferrocenophanes
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Two novel ester ferrocenophanes have been prepared by esterification of 1,1′-ferrocenedi(carbonyl chloride) with glycol and 1,4-butanediol, respectively. Both of them have been characterized by IR, elemental analysis, MALDI-TOF MS and 1H NMR spectroscopic methods, and their structures have been elucidated by X-ray diffraction. The intermolecular associations based on C - H?O hydrogen bonds have also been discussed. These molecules are assembled into chains, and the chains are further assembled into a 3D structure through several hydrogen bonds.
- Li, Tao,Yang, Bingqin,Gao, Bo
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- Synthesis of Ferrocene-Based Pyridinones through Rh(III)-Catalyzed Direct C-H Functionalization Reaction
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Synthesis of ferrocene-based pyridinones via Rh(III)-catalyzed annulation of ferrocenecarboxamides with internal alkynes has been developed using a directing group as the internal oxidant. This method displays good functional group tolerance and delivers ferrocene-based pyridinones generally in moderate to good yields. Additionally, an asymmetric reaction can be achieved in the presence of a chiral catalyst Rh1.
- Wang, Shao-Bo,Zheng, Jun,You, Shu-Li
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- Iron oxide decorated N-doped carbon derived from poly(ferrocene-urethane) interconnects for the oxygen reduction reaction
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We report the synthesis of mixed iron oxide particles decorated on nitrogen-doped carbon by forming covalent polyurethane linkages between ferrocene and phloroglucinol. Contrasting the electrostatic interactions and the physical cross-linking of the Fe/N/C precursors, here poly(ferrocene-urethane) (PFU) was acquired exclusively by (i) conversion of dicarboxylic acids present in ferrocene to azide linkages; and (ii) chemically linking the ferrocene-diazides to phloroglucinol through urethane bonds. The as obtained poly(ferrocene-urethane) was pyrolyzed under argon at elevated temperatures (600, 800 and 1000 °C) to yield iron oxide decorated N-doped carbon interconnects. The resultant porous materials were found to have the right balance of hierarchical porosity (micro-, meso- and macro-), and N-doping and iron oxide phases in and on the carbon matrices, respectively. Among the PFU samples pyrolyzed at different temperatures, the sample pyrolyzed at 800 °C displayed a more positive onset potential, a higher current density, and direct four electron transfer kinetics with a lesser yield of H2O2 (5.6%) on par with the commercially available Pt catalysts for the oxygen reduction reaction (ORR) in alkaline KOH solution. The superior electrocatalytic activity of PFU-800 can be traced to the synergistic effect between the iron oxide on and N-doping of the porous carbon nanostructures and the balanced hierarchial porosity. The developed non-Pt based electrocatalyst can be considered as a promising electrocatalyst in alkaline fuel cell applications.
- Premkumar, Viji,Chandrasekaran, Naveen,Madasamy, Kanagaraj,Kathiresan, Murugavel,Kanagavalli, Pandiyaraj,Senthil Kumar, Shanmugam
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- Synthesis and combustion catalytic activity of ferrocene-based energetic compounds
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Ammonium perchlorate (AP) is a common oxidizer in composite solid rocket propellants due to its excellent burning characteristics, good processability, and storability. Owing to their outstanding catalytic effects, ferrocene, and its derivatives have become the most widely used burning rate catalysts (BRCs). The addition of ferrocene and its derivatives to AP rendered performance optimization. In this study, azole-based ferrocenyl compounds were successfully synthesized. The compounds were characterized by single-crystal X-ray diffraction, UV-vis spectroscopy, and other techniques. The thermal degradation of AP catalyzed by these compounds was evaluated by differential scanning calorimetry and thermogravimetric analysis. Results revealed that the decomposition peak temperature of AP dramatically decreases and that the released heat of AP significantly increases with the new compounds as additives. Hence, the six azole-based ferrocenyl BR catalysts are favorable for the combustion catalytic activity.
- Huang, Shiqi,Yang, Rong,Wang, Jiaodan,Chang, Shuai,Gou, Xiaofeng,Hua, Chengwen,Zhao, Junlong
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- Redox-Triggered Chirality Switching and Guest-Capture/Release with a Pillar[6]arene-Based Molecular Universal Joint
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A chiral electrochemically responsive molecular universal joint (EMUJ) was synthesized by fusing a macrocyclic pillar[6]arene (P[6]) to a ferrocene-based side ring. A single crystal of an enantiopure EMUJ was successfully obtained, which allowed, for the first time, the definitive correlation between the absolute configuration and the circular dichroism spectrum of a P[6] derivative to be determined. The self-inclusion and self-exclusion conformational change of the EMUJ led to a chiroptical inversion of the P[6] moiety, which could be manipulated by both solvents and changes in temperature. The EMUJ also displayed a unique redox-triggered reversible in/out conformational switching, corresponding to an occupation/voidance switching of the P[6] cavity, respectively. This phenomenon is an unprecedented electrochemical manipulation of the capture and release of guest molecules by supramolecular hosts.
- Cheng, Guo,Chruma, Jason J.,Kanagaraj, Kuppusamy,Liang, Wenting,Su, Dan,Wu, Wanhua,Xiao, Chao,Yang, Cheng,Zhong, Zhihui,Zhou, Dayang
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- First examples of bispidine-ferrocene cyclophanes
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Two approaches for the syntheses of bispidine-ferrocene cyclophanes were reported. Both include the acylation of 1,5-dimethylbispidin-9-one (H2Bp) or its pendant amino-armed derivative by 1,1’-ferrocenoyl (Fc(CO)2) dichloride. The first approach allowed to isolate di-, tri- and pentameric cyclic oligomers of composition (BpFc(CO)2)n. The second one included the preliminary functionalization of H2Bp by N-protected glycine followed by deprotection and cyclization with Fc(COCl)2. The crystal structure of two new bispidine-ferrocene cyclophanes was established by single-crystal X-ray study. This study revealed the anti-conformation of amido-groups attached to the bispidine nitrogen atoms for both molecules. Various NMR techniques were applied to study the solution behavior of the macrocycles; the predominant anti-conformation in solution was also proved. The acyclic model compound Bp(FcCO)2 also showed only anti-conformer as revealed by VT-NMR and X-ray studies. Cyclic voltammetry study showed the difference in oxidation potentials of the Fc moiety within the row Bp(FcCO)2 – (BpFc(CO)2)2 – (BpFc(CO)2)3 with splitting of the oxidation curve in two later cases. The results obtained in this work will find an application in design and study of novel bispidine-ferrocene cyclophanes for the purposes of supramolecular sensing and catalysis.
- Churakov, A. V.,Gaisen, S. V.,Krut'ko, D. P.,Lemenovsky, D. A.,Medved'ko, A. V.,Minyaev, M. E.,Moiseeva, A. A.,Vatsadze, S. Z.,Wang, L.,Yu, H.
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supporting information
(2021/06/28)
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- Molecularly engineered oxygen deficient magnetite decorated carbon as electrocatalysts for oxygen reduction reaction
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Herein, we report the in situ synthesis of poly (ferrocene-urea) (PFUA) by reacting ferrocene diacylazide and tris (4-aminophenyl) amine. The formation of urea linkages between the precursors was confirmed by Fourier transform Infrared (FTIR) spectroscopy
- Adith, Ramakrishnan Velmurugan,Madasamy, Kanagaraj,Ebenezer, James,Mohanapriya, Nagarajan,Kosame, Saikiran,Ramesh, Balamurugan Kesani,Kathiresan, Murugavel,Kumar, Shanmugam Senthil,Chandrasekaran, Naveen
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- Redox-active binary eutectics: Preparation and their electrochemical properties
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Eutectics are emerging as promising candidate for electrochemical energy storage. However, the eutectics usually show high viscosity that usually arises from strong intermolecular interactions greatly limits their application. In this communication, we design and prepare two redox-active molecules that both are able to form binary eutectics with TBMA-TFSI. Combined experimental and computational studies indicate the intermolecular interaction is weakened after eutectic formation, resulting in decreased viscosity and enhanced ionization ratio of TBMA-TFSI without affecting the redox behaviors of the individual molecules. Further, the redox-active binary eutectic is used as solvent-free electrolyte for battery application.
- Chen, Hui,Niu, Zhihui,Zhao, Yu
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- Synthesis and Cytotoxicity of the Dihydroartemisinin Ester of 1,1′-Ferrocenedicarboxylic Acid
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The synthesis of the dihydroartemisinin ester of 1,1′-ferrocenedicarboxylic acid (III) is described. Results of in vitro studies of its effect on the viability of cell cultures of fibroblasts and tumor cells (K562, HEp-2, HeLa) are presented. The selectivity of III at a concentration of 125 μM was 1.2 times greater for myelogenous leukemia cells (K562) than for fibroblasts, indicating that its antiproliferative activity against tumor cells was selective and that in vivo studies of antitumor compound III were feasible, especially for cases of iron-deficiency anemia.
- Shaikhina,Semeikin,Gudovshchikov,Pavlik,Shimanovsky
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p. 536 - 539
(2021/10/01)
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- New π-Extended 1,1′-Disubstituted Ferrocenes with Thioate and Dithioate End Groups
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Extended π systems based on 1,1′-aryl or (2-arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of mole
- Butensch?n, Holger,Schmiel, Sinem-Fatma
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p. 2388 - 2401
(2021/06/25)
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- A [...] of highly dilute preparation method
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A [...] of highly dilute preparation method, comprises the following steps: step 1), in the added into the dry CH [...] in2 Cl2 , Pyridine and aniline derivatives stirring after; step 2), non-water treated CH2Cl2 dissolved 1, 1' - ferrocene dicarboxylic acyl chloride, to slowly dropping in the [...], after dropping the first reaction is carried out at room temperature, then slow heating, reflux; monitoring the reaction process for thin plate and, when one of the raw material point disappears, stopping the reaction; step 3), evaporate solution in dichloromethane, residual liquid water washing several times, the collected organic phase with anhydrous MgSO4 After drying the solvent evaporate under reduced pressure, then to admix the residual liquid in the silica gel, eluting agent selected: VPetroleum ether : VAcetic acid ethyl ester =3:1 elution, column purification, to obtain a final [...]. The invention can simplify the link flourishing synthetic process, improve its productive rate with the fluorescence intensity, save the process cost.
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Paragraph 0032; 0038; 0044; 0049
(2018/10/19)
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- Synthesis and characterization of ferrocenyl esters: Their anti-oxidant activity and DNA-binding ability
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In continuation to our work on biologically active material, some new ferrocenyl esters were prepared by condensation of 4-ferrocenyl phenol (ROH) with ferrocenyl dicarboxylic acid chlorides (DCC) at low temperature. The synthesized compounds (E1-E9) were characterized by analyzing their physical properties, FT-IR, 1H-NMR, UV-visible spectroscopic and cyclic voltammetric studies. The DPPH free radical scavenging assay was performed to explore their potential as antioxidant which showed that the E1 had maximum scavenging ability (77.11%) whereas E3 showed minimum (52%) compared with the standard. Cyclic voltammetric studies indicated that these compounds were electroactive in potential window of 2.0-0.0V. Binding mode found in these esters was an electrostatic interaction which is considered as strongest amongst all. Therefore, these compounds are considered to have DNA-binding capability and are potential DNA binders.
- Bukhari, Syeda Anam,Gul, Asghari,Akhter, Zareen,Bashir, Amna
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p. 375 - 382
(2018/06/06)
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- Method for preparing ferrocenyl phosphine oxide ligand
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The invention discloses a simple, convenient and quick preparation method for synthesizing a ferrocenyl phosphine oxide ligand. The method comprises the steps of firstly, carrying out a Friedel-Crafts acylation reaction on ferrocene which serves as a starting raw material so as to obtain acyl ferrocene, carrying out a reaction with p-toluenesulfonhydrazide so as to produce a ferrocenyl-containing p-toluenesulfonylhydrazone compound, and carrying out a reaction with a phosphorus oxide containing phosphorus-hydrogen bonds under the catalysis of copper to form a carbon-phosphorus bond, thereby obtaining the ferrocenyl phosphine oxide. According to the method disclosed by the invention, reaction steps are few, the operation is simple and convenient, the yield is high, and the tolerance to functional groups is very good. By the method, ferrocenyl phosphine oxide ligands containing a variety of different substituents can be synthesized.
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Paragraph 0022; 0026; 0030
(2017/10/11)
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- A ferrocene naphthyridine derivatives and its preparation and use
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The invention relates to a ferrocene naphthyridine derivative and preparation and an application thereof. The novel ferrocene naphthyridine derivative designed and synthesized by the invention is high in production rate and low in cost, and can effectively identify and absorb Hg in a liquid, also has a recognition effect on Cu, and has a broad application prospect in environmental purification.
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Paragraph 0057
(2017/08/25)
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- Ferrocenyl-based redox-reversible surfactant and preparation method of thereof
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The invention provides a ferrocenyl-based redox-reversible surfactant and a preparation method thereof, and relates to the field of redox switch type surfactants. The ferrocenyl-based redox-reversible surfactant is prepared from a precursor compound ferrocene, acetyl chloride, zinc amalgam, bromoundecanoic acid, thionyl chloride and trimethylamine as raw materials. The synthesized surfactant molecules are easy to prepare, the yield of the intermediate diacetylferrocene is effectively improved, a new feeding sequence is provided, and the problem of reduction of ferrocene due to oxidation reaction is effectively solved. The surfactant can be used as an electrode surface modification material for glucose detection.
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Paragraph 0020; 0021
(2018/01/19)
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- Ruthenium-Catalyzed Enantioselective Hydrogenation of Ferrocenyl Ketones: A Synthetic Method for Chiral Ferrocenyl Alcohols
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Highly effective asymmetric hydrogenation of various ferrocenyl ketones, including aliphatic ferrocenyl ketones as well as the more challenging aryl ferrocenyl ketones, was realized in the presence of a Ru/diphosphine/diamine bifunctional catalytic system. Excellent enantioselectivities (up to 99.8% ee) and activities (S/C = 5000) could be obtained. These asymmetric hydrogenations provided a convenient and efficient synthetic method for chiral ferrocenyl alcohols, which are key intermediates for a variety of chiral ferrocenyl ligands and resolving reagents.
- Lu, Bin,Wang, Qun,Zhao, Mengmeng,Xie, Xiaomin,Zhang, Zhaoguo
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p. 9563 - 9569
(2015/10/12)
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- CuI catalyzed Barbier type allylation of aldehyde in presence of S1,S2-dipyridin-2-yl ferrocene-1,1′-dicarbothioate as ligand
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Ferrocene based ligand S1 ,S2-dipyridin-2-yl ferrocene-1,1′-dicarbothioate has been prepared from 1,1′-ferrocene-dicarboxylic acid. The ligand has been used successfully in the SnCl2.2H2O mediated Barbier type a
- Kashyap, Bishwapran,Phukan, Prodeep
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p. 662 - 670
(2015/05/27)
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- Visual detection and removal of mercury ions by a ferrocene derivative
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New ferrocene naphthyridine derivatives were successfully synthesized. The di-substituted ferrocene derivative FecDN behaves as a selective visual chemosensor for mercury ions, exhibiting a rapid and clearly visible precipitation with good selectivity (precipitation) and sensitivity (0.01 μM). The interaction of the ferrocene derivatives and metal ions was investigated by ultraviolet-visible spectroscopy (UV-vis), electrochemical methods, 1H NMR, as well as infrared (IR), and energy dispersive X-ray spectroscopy (EDX). The application of FecDN in the detection and removal of mercury ions is very simple, rapid, and intuitive.
- Peng, Xiaoqian,He, Hanping,Xia, Jingping,Lou, Zhaowen,Chang, Gang,Zhang, Xiuhua,Wang, Shengfu
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p. 3541 - 3544
(2014/06/10)
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- Synthesis, molecular structure and properties of a ferrocene-based difluoropyrrolo-oxaborole derivative
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Reaction of 1,1′-ferrocenedicarbonyl chloride with 3-ethyl-2,4-dimethylpyrrole in DCM produced the half-way product, namely, the ferrocene bis(2-ketopyrrole) derivative 2 and not the expected bis(dipyrromethene) compound. The 2-ketopyrrole compound readily reacted with BF3·Et2O to produce the bis(difluoropyrrolo)-oxaborole compound, FBF, as a red/brown solid which was characterised by X-ray crystallography. 57Fe M?ssbauer spectra for 2 and FBF were consistent with low-spin iron(II) (d6) ferrocene derivatives. A cyclic voltammogram for 2 in acetonitrile revealed a reversible wave at +0.31 V vs. Fc+/Fc (ferrocene-based) and an irreversible wave at -2.38 V vs. Fc+/Fc (ketopyrrole-based). The electrochemical behaviour is severely perturbed by the chelation of the BF2 groups. Alterations to the electronic properties of 2 by formation of FBF are also evident in the absorption profiles. DFT calculations [B3PW91, 6-31G(3df)] support the observed changes in the electrochemistry findings and the M?ssbauer spectroscopic data. Reaction of 1,1′-ferrocenedicarbonyl chloride with 3-ethyl-2,4-dimethylpyrrole produces the bis(ketopyrrole) compound. Chelation of BF2 to the ketopyrrole units forms the difluoropyrrolo-oxaborole.
- Benniston, Andrew C.,Sirbu, Dumitru,Turta, Constantin,Probert, Michael R.,Clegg, William
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supporting information
p. 6212 - 6219
(2015/02/19)
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- A new ferrocene-based bulky pyridine as an efficient reusable homogeneous catalyst
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An effective approach to reusing a homogeneous catalyst has been demonstrated. A ferrocene-based bulky pyridine has been synthesized and utilized as a homogeneous catalyst for the synthesis of benzoylfumarates as well as for acetylation. After the reaction, the catalyst was separated by simple precipitation and reused without appreciable loss of activity. The Royal Society of Chemistry 2013.
- Kashyap, Bishwapran,Phukan, Prodeep
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p. 15327 - 15336
(2013/09/02)
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- Synthesis, characterization and morphological studies of some novel siloxane-based block copolymeric materials containing organometallic as well as organic polyesteramides
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A series of semi-aromatic diamine monomers (1,m-bis (4-amino benzoyloxy) alkanes; m = 2-6) having in-built ester linkages with variable methylene spacers were synthesized in two steps from aliphatic diols and p-nitrobenzoyl chloride and characterized by their melting points, elemental analysis, FTIR, 1H and 13C NMR spectroscopic studies. The diamines were then polymerized in-situ with ferrocene-based organometallic and terephthaloyl- as well as isophthaloyl-based organic acyl chlorides along with telechelic polydimethylsiloxane oligomer to produce a novel set of ferrocene-containing siloxane-based block copolymers and their organic analogues. The corresponding polyesteramides of the synthesized copolymers, without siloxane segment, were also prepared for comparative studies. The structural features of the organometallic and organic block copolymers along with their respective polyesteramides were confirmed by their physical properties and spectroscopic studies. The molecular parameters of all these materials were determined by static laser light scattering (LLS) technique and glass transition temperatures (Tg) were obtained by differential scanning calorimetry (DSC). The materials were soluble in sulphuric acid and partially soluble in common organic solvents at room temperature, yet become readily soluble upon N-trifluoroacetylation. The morphological information of the synthesized materials was obtained by X-ray diffraction and surface studies (SEM and AFM).
- Saif Ullah Khan, Muhammad,Akhter, Zareen,Iqbal, Naseer,Siddiq, Mohammad
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p. 312 - 328
(2013/10/01)
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- Ferrocene-tryptophan conjugate: An example of a redox-controlled reversible supramolecular nanofiber network
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In this study, the tryptophan derivative of ferrocene-1,1′- dicarboxylic acid self-assembles in toluene to form a supramolecular nanofibrillar network structure. The ferrocene bioconjugate based nanofibers are responsive toward oxidation/reduction and show thermo and redox reversibility. Interestingly, redox-induced reversible morphological transformations between nanofiber and spheroid were observed. The self-assembly was characterized by 1H NMR spectroscopy, FT-IR spectroscopy, UV-vis spectroscopy, circular dichroism (CD), and transmission electron microscopy (TEM).
- Adhikari, Bimalendu,Afrasiabi, Rouzbeh,Kraatz, Heinz-Bernhard
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p. 5899 - 5905
(2013/11/19)
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- Synthesis and characterization of a new dinuclear platinum(II) alkynyl complex with a ferrocene bridge and its interaction with silver ion
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A new dinuclear alkynyl platinum(II) complex with a ferrocene (Fc) bridge (Pt(II)-Fc-Pt(II)), referred as Sensor 1(1), was synthesized and characterized. The photophysical, luminescent and cation-binding properties were studied by UV-Vis spectrophotometric, fluorometric, 1H NMR titration methods, and the ESI-MS. Sensor 1 showed a significant luminescent quenching in the presence of silver ions (Ag+).
- Uahengo, Veikko,Zhou, Nana,Xiong, Bi,Cai, Ping,Hu, Kai,Cheng, Gongzhen
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p. 102 - 108
(2013/06/27)
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- Modification of Sn/S cages with bis-functionalized ferrocenyl units
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Bis-functionalized ferrocenyl units have been attached to organo-functionalized [(RFSn)4S6] double-decker clusters as criss-cross-type intramolecular straps. Two different ways of linking result in different crystal struct
- You, Zhiliang,Fenske, Dieter,Dehnen, Stefanie
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supporting information
p. 8179 - 8182
(2013/07/19)
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- Synthesis and characterization of a ferrocene-linked bis-fullerene[60] dumbbell
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A new [60]fullerene dumbbell consisting of two fulleropyrrolidines connected to a central ferrocene unit by amide linkages has been prepared and fully characterized by elemental analysis, 1H NMR, UV/Vis, fluorescence and mass spectrometry. The electrochemical properties as determined by cyclic voltammetry show ground state electronic communication between the ferrocene and the fullerene units. In addition, the preparaton of a ferrocene building block for an alternative linking approach is presented. The Royal Society of Chemistry 2012.
- Andersson, Claes-Henrik,Nyholm, Leif,Grennberg, Helena
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p. 2374 - 2381
(2012/03/22)
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- Efficient regio- and diastereo-controlled synthesis of 1,1′- and 1,1′,2,2′-functionalised ferrocenes and the formation of 2-oxa[3]ferrocenophanes
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The synthesis of a C2 symmetric 1,1′ ,2,2′-tetrasubstituted ferrocene system was discussed. The route involved the reduction of ferrocenyl carbonyl compounds which gave access to a range of alcohols, alkenes, alkanes, ethers, and 2-oxa[3]ferrocenophanes depending on the precise conditions used. The loss of optical activity of 1,1′-bis(hydroxymethyl)ferrocenes and 1,1′-bis(hydroxymethyl)ruthenocenes, which had been prepared by asymmetric reduction, was demonstrated in an acidic medium by extensive 1H NMR studies.
- Carroll, Michael A.,White, Andrew J.P.,Widdowson, David A.,Williams, David J.
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p. 1551 - 1557
(2008/10/08)
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- The effect of protonation on the spectroscopic and redox properties of a series of ferrocenoyl derivatives
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Five ferrocenoyl derivatives, containing pyridine (1-4) and benzene (5) moieties, were synthesised and characterised. The effect on the spectroscopic and redox properties of these compounds upon addition of H+ was studied, with NMR studies indicating that protonation took place at the pyridine nitrogens of 1-4. A crystal structure determination of the bis(amide) derivative 4 revealed the presence of two intramolecular hydrogen bonds; these remained intact in solution but were cleaved upon protonation. Protonation induced anodic shifts in the ferrocene-centred redox potential of ferrocene receptors 1, 2 and 4 and also changes in the electronic and NMR spectra of 1-4. A bathochromic shift in the lowest energy spin-allowed d-d band upon protonation was only observed for those compounds which also displayed a pronounced redox response.
- Carr, Jonathan D.,Coles, Simon J.,Hassan, William W.,Hursthouse, Michael B.,Malik, K. M. Abdul,Tucker, James H. R.
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- 1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reactions of ferrocene
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Friedel-Crafts acylations of ferrocene in 1-ethyl-3-methylimidazolium halogenoaluminate ionic liquids, [emim]I-(AlCl3)x are described.3 The effect of varying the "bulk" Lewis acidity of the ionic liquids used as solvents in these reactions and the effect of varying the relative amounts of acylating agent with respect to the amount of ferrocene in these reactions is also described. The use of a variety of different acylating agents in our studies demonstrates the scope of this reaction performed in these ionic liquid systems.
- Stark, Annegret,MacLean, Bonnie L.,Singer, Robert D.
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- Sequential Friedel-Crafts diacetylation of ferrocene: Interannular proton transfers as a mechanistic probe
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(Pentadeuteriocyclopentadienyl)cyclopentadienyliron(II), 4, was prepared by the sequential addition of lithium tris(trimethylsilyl)cyclopentadienide and lithium pentadeuteriocyclopentadienide to FeBr2 followed by fluoride-induced removal of the trimethylsilyl groups of the resulting ferrocene 3. Analysis of the deuterium content of the acetylferrocene 5 and the 1,1′-diacetylferrocene 7, obtained from the Friedel-Crafts acetylation of 4, reveals that the former is formed by initial exo attack of AlCl3-CH3COCl, whereas precomplexation of the electrophile at the metal center (endo attack) precedes the formation of the latter.
- Cunningham Jr., Allan F.
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p. 2480 - 2485
(2008/10/08)
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- Friedel-crafts acetylation of bis(trimethylsilyl)- and bis(tributylstannyl)ferrocene: implications on the mechanisms of acylation and proton exchange of ferrocene derivatives
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The first unequivocal examples of intermolecular Friedel-Crafts reactions of ferrocene derivatives proceeding via exo attack of the electrophile are reported. Treatment of 1,1′-bis(trimethylsilyl)-(5a) or 1,1′-bis(tributylstannyl)ferrocene (5b) with acetyl chloride in the presence of AlCl3 affords a mixture of three isomeric acetylferrocenes, 1′-acetyl- (6), 2-acetyl-(7), and 3-acetyl-1-(trialkylsilyl and -stannyl)ferrocene (8). Acetylation of 3,3′-dideutero-1,1′-bis(trimethylsilyl)ferrocene (5aD2) under identical conditions generates the corresponding dideuterated products 6aD2-8aD2. Both 6aD2 and 7aD2 contam 1.0 deuterium atom in each cyclopentadienyl ring whereas 8aD2 contains 05 deutenum atom in the substituted ring and 1.5 deuterium atoms in the unsubstituted ring. This demonstrates that the products are formed via exo attack of the electrophile followed by an intramolecular, interannular proton transfer. The lack of scrambling of the deuterium label also suggests that protonation of ferrocenes could also occur through the exo attack of a proton rather than direct protonation at the metal center.
- Cunningham Jr., Allan F.
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p. 4864 - 4870
(2007/10/02)
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