49547-67-3

Upstream product

• 102-54-5 ferrocene 
• 609-65-4 o-chlorobenzoyl chloride 

Downstream Products

• 89670-29-1 (+/-)-α-hydroxy(2-chlorobenzyl)ferrocene 
• 287180-12-5 (2-chlorobenzyl)ferrocene 
• 638222-80-7 [FcC(OTMS)(CN)(o-ClC₆H₄)] 
• 1271-42-7 ferrocenecarboxylic acid 

Relevant academic research and scientific papers

Ferrocenyl Janus mixed-dendron stars and their stabilization of Au and Ag nanoparticles

Janus molecular architectures have recently attracted attention due to their structures and properties that differ from those of traditional symmetric structures. Herein, two new small redox-reversible mixed-dendron star-shape molecules containing three ferrocenyl groups have been synthesized by linking two distinct dendrons using an esterification reaction. These organometallic nano structures were characterized by 1H and 13C NMR, MS, IR and UV–vis. spectroscopies and cyclic voltammetry confirming the number of ferrocenyl groups and AFM and DLS showing micellar assemblies. Au and Ag nanoparticles were stabilized in the presence of a mixed-dendron structure having amidoferrocene termini upon reaction of the nanoparticle metal precursor with NaBH4. Compared reactions of the two star-molecules with HAuCl4 showed a slow redox reaction leading to Au nanoparticles only with the star-molecule terminated with triazolyferrocene termini, which is taken into account by the difference of their redox potentials.

Independent Quantification of Electron and Ion Diffusion in Metallocene-Doped Metal-Organic Frameworks Thin Films

The chronoamperometric response (I vs t) of three metallocene-doped metal-organic frameworks (MOFs) thin films (M-NU-1000, M = Fe, Ru, Os) in two different electrolytes (tetrabutylammonium hexafluorophosphate [TBAPF6] and tetrabutylammonium tetrakis(pentafluorophenyl)borate [TBATFAB]) was utilized to elucidate the diffusion coefficients of electrons and ions (De and Di, respectively) through the structure in response to an oxidizing applied bias. The application of a theoretical model for solid state voltammetry to the experimental data revealed that the diffusion of ions is the rate-determining step at the three different time stages of the electrochemical transformation: an initial stage characterized by rapid electron diffusion along the crystal-solution boundary (stage A), a second stage that represents the diffusion of electrons and ions into the bulk of the MOF crystallite (stage B), and a final period of the conversion dominated only by the diffusion of ions (stage C). Remarkably, electron diffusion (De) increased in the order of Fe 6 1- as the counteranion in all the stages of the voltammogram, demonstrating the strategy to modulate the rate of electron transport through the incorporation of rapidly self-exchanging molecular moieties into the MOF structure. The De values obtained with larger TFAB1- counteranion were generally in agreement with the previous trend but were on average lower than those obtained with PF6 1-. Similarly, the ion diffusion coefficient (Di) was generally higher for TFAB1- than for PF6 1- as the ions diffuse into the crystal bulk, due to the high degree of ion-pair association between PF6 1- and the metallocenium ion, resulting in a faster penetration of the weakly associated TFAB1- anion through the MOF pores. These structure-function relationships provide a foundation for the future design, control, and optimization of electron and ion transport properties in MOF thin films.

Nitro-imidazoles in ferrocenyl alkylation reaction. Synthesis, enantiomeric resolution and in vitro and in vivo bioeffects

Ferrocenylalkyl nitro-imidazoles (4a-h, 5a-h) were prepared via the regiospecific reaction of the α-(hydroxy)alkyl ferrocenes, FcCHR (OH) (1a–h; Fc = ferrocenyl; R = H, Me, Et, Pr, i-Pr, Ph, ortho-Cl-Ph, ortho-I-Ph), with nitro-imidazoles in aqueous organic medium (H2O-CH2Cl2) at room temperature in the presence of HBF4, within several minutes in good yields. X-ray structural data for racemic (R,S)-1-N-(benzyl ferrocenyl)-2-methyl-4-nitroimidazole (5f) were determined. The resulting enantiomers were resolved into enantiomers by analytical HPLC on modified amylose or cellulose chiral stationary phases. The viabilities of 4b, 4d, 5b, 5c in vitro, and in experiments in vivo antitumor effects of 1-N-ferrocenylethyl-4-nitroimidazole (4b) against murine solid tumor system Ca755 carcinoma were evaluated.

Synthesis of the ferrocenyl analogue of clotrimazole drug

The ferrocenyl analogue of clotrimazole, in which the metallocene fragment replaces one of the phenyl rings in the triphenylmethane system, and a related isomer were prepared through the direct substitution of a methoxygroup in the α-position to ferrocene with imidazole in the key step. The obtained ferrocenyl derivatives were spectroscopically characterized and in a preliminary assay for bioactivity their cell growth inhibitory activity on two different human cancer cell lines was evaluated. In comparison with the parent drug the ferrocene analogues displayed about two-fold increase of cytotoxicity on HT29 colorectal cancer cells, whereas comparable activity was displayed against MCF-7 breast cancer cell line.

Ruthenium-Catalyzed Enantioselective Hydrogenation of Ferrocenyl Ketones: A Synthetic Method for Chiral Ferrocenyl Alcohols

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.

Syntheses, third-order optical nonlinearity and DFT studies on benzoylferrocene derivatives

A series of benzoylferrocene derivatives were synthesized and their third-order nonlinear optical (NLO) properties were evaluated in N,N-dimethyl-formamide at 800 nm using femtosecond degenerate four-wave mixing. The third-order NLO susceptibilities of synthesized compounds were 3.065-7.859 × 10-13 esu, with the response times in 49-70 fs. The second-order hyperpolarizabilities of the molecules of the compounds were 1.018-2.611 × 10-31 esu. The Density Functional Theory was used to calculate these benzoylferrocene derivatives. The theoretical study showed that the third-order NLO properties were increased with the increasing electron-withdrawing ability, which is accordance with the decreasing energy gap between the highest occupied and the lowest unoccupied molecular orbital. With the increasing of electron-withdrawing ability, the transferred charge to the substituent was increased and the affection on the electronic reallocate was increased. The experiment and theoretical results showed that the benzoylferrocene derivatives had potential nonlinear optical applications.

SUBSTITUTED BENZOYLFERROCENE ANIONIC PHOTOINITIATORS

The present invention relates to anionic photoinitiator compounds, compositions containing them, and methods of using them having the structure: wherein X and Y are independently selected from the group consisting of a direct single bond and -C(=O)-, wher

Efficient regio- and diastereo-controlled synthesis of 1,1′- and 1,1′,2,2′-functionalised ferrocenes and the formation of 2-oxa[3]ferrocenophanes

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.

Efficient photodissociation of anions from benzoyl-functionalized ferrocene complexes

Spectroscopic and photochemical studies of several benzoyl-functionalized ferrocene complexes in nonaqueous solvents are reported. Bands observed above 300 nm in the electronic absorption spectrum of the unsubstituted complex, Fe(n5-C5H5)2, and assigned to ligand field transitions shift to longer wavelengths and intensify upon introduction of a benzoyl group into one or both cyclopentadienide rings. Such .behavior suggests that these transitions have acquired some charge-transfer character. Visible-light (546 nm) irradiation of l.l'-dibenzoyl-ferrocene, III, dissolved in CH3CN, CH3OH, or ethyl α-cyanopropionate causes ring-metal cleavage to produce the benzoylcyclopentadienide ion, C6H5C(O)C5H4-, and the corresponding half-sandwich cationic complex, Fe[(n5-C5H4)C(O)C6H 5](S)3+ (S is solvent). The disappearance quantum yield, odis, for III is 0.45 in CH3OH and 0.28 in ethyl α-cyanopropionate and is unaffected by the presence of dissolved O2, added H2O (10 000 ppm), or added methanesulfonic acid (30 ppm). l,l′-Dibenzoylferrocenes containing substitutents on both phenyl rings undergo photoinduced ring-metal cleavage in CH3OH with odis values very similar to that of III, while monobenzoyl-ferrocenes are appreciably less photoreactive. A mechanism that accommodates the photochemical behavior of benzoyl-functionalized ferrocene complexes is discussed. In addition, a previous suggestion concerning the role of III in the photoinitiated anionic polymerization of an α-cyanoacrylate monomer is reconsidered in light of the present study.

13C CHEMICAL SHIFTS AND CARBONYL STRETCHING FREQUENCIES AS STRUCTURAL PROBES FOR FERROCENYL KETONES

13C chemical shifts (δ(CO)) have been measured for a series of aromatic ferrocenyl ketones (FcCOC6H4X) and some sterically hindered analogues (FcCOR, R=mesityl, anthracyl, t-Bu, adamantyl).The shifts correlated quite well with those of the corresponding benzophenones.From the carbonyl carbon shifts (δ(CO)), estimates were made of the interplanar angle between the carbonyl sp2 and the phenyl ring planes.Substituent effects of the Cp ring carbons are discussed.The solution (CCl4) infrared spectra of the derivatives were obtained and the carbonyl stretching frequency (ν(CO)) was found to correlate roughly with δ(CO).Estimates were also made of the interplanar angle between the cyclopentadienyl ring plane and the carbonyl plane, for sterically hindered ketones using δ(CO) values.