12085-68-6Relevant articles and documents
Design, synthesis and fungicidal activity studies of 3-ferrocenyl-N-acryloylmorpholine
Chen, Peiqi,Liu, Chunjuan,Hu, Jianfeng,Zhang, Hao,Sun, Ranfeng
, p. 113 - 121 (2018)
Ferrocene and its derivatives have been widely used in many fields and also used to modify and improve the performance. Particularly, their low toxicity also attract much attention in medical and pesticide fields. In order to get fungicides with higher biological activity, ferrocenyl groups were introduced into the skeleton of dimethomorph instead of phenyl groups and a series of 3-ferrocenyl-N-acryloylmorpholine were synthesized. The fungicidal bioassay results indicated that most of compounds showed moderate fungicidal activities against 14 kinds of agricultural pathogenic fungi and some compounds displayed higher fungicidal activities than that of dimethomorph. Intrestlingly, compounds 5(Z) exhibited better fungicidal activity against Sclerotinia sclerotiorum than that of compound 5(E).
Synthesis of a diferrocenylvinylidene complex by migration of a ferrocenyl substituent
Korb, Marcus,Moggach, Stephen A.,Low, Paul J.
, p. 4251 - 4254 (2021)
An unusual 1,2-ferrocenyl migration has been observed following reactions of [Ru(dppe)Cp][BArF4] with diferrocenylacetylene, extending the scope of group rearrangments beyond methyl (Wagner-Meerwein) and phenyl entities. Ferrocene-containing bis(alkynes) RCCArCCR (R = Fc, Ar = 1,4-phenylene; R = Ph, Ar = 1,1′-ferrocenylene) gave bimetallic bis(vinylidene) complexes following two consecutive rearrangements.
New π-Conjugated Ferrocenyl-Substituted Heterocyclic Systems Containing Electron-Deficient Aromatic Nitrogen Heterocycles
Antuf’eva,Dmitriev,Maiorova,Mokrushin,Galeev,Shklyaeva,Abashev
, p. 1350 - 1357 (2018)
A series of ferrocenyl-substituted methyl ketones and chalcones were synthesized and converted to unsymmetrical 4,6-disubstituted pyrimidin-2-amines and 2-(1H-pyrrol-1-yl)pyrimidines in which the ferrocene fragment is separated from the pyrimidine ring by
Iodine catalysed unprecedented synthesis of ferrocenated thiols and bis-dithianes: Chemoselectivity and smart phone based metal sensing application
Ali, Munsaf,Joshi, Raj K.,Sahoo, Suban K.,Srivastava, Avinash K.,Upadhyay, Yachana
, (2020)
Acetalisation of (2-Formyl-1-chlorovinyl)ferrocene with various acyclic and cyclic thiols leads to the synthesis of a variety of ferrocenated mono-, bis- and di-thianes. The series of ferrocene-substituted thiols is synthesized for the first time. The excellent yield of both the thiols and dithianes compounds was obtained under mild reaction conditions in the catalytic presence of molecular iodine. Also, the chemoselective acetalisation of (2-Formyl-1-chlorovinyl)ferrocene, 2-(1,3-dioxan-2-yl)-1-ferrocenylethanone and 2-(1,3-dioxolan-2-y1)-1-ferrocenylethanone towards 1,2- and 1,3-dithiols shows formation of different products. It is also noticed that the transthioacetalisation of 1,3-O,O acetal or 1,2-O,O acetal is dominant over acetalisation of ketones. The mono/dithiane compounds show the promising applications in the optical sensing of Hg2+ at remarkably low concentrations.
The synthesis, structural characterization and biological evaluation of novel N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters as anticancer agents
Harry, Andy G.,Murphy, James P.,O'Donovan, Norma,Crown, John,Rai, Dilip K.,Kenny, Peter T.M.
, p. 379 - 388 (2017)
A series of N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters 4–18 were prepared by coupling para-(ferrocenyl) ethynyl benzoic acid 3 to the amino acids GABA(OMe), GABA(OEt) and the dipeptide esters GlyGly(OMe), GlyGly(OEt), Gly-L-Ala(OMe), Gly-L-Ala(OEt), Gly-D-Ala(OMe), Gly-D-Ala(OEt), Gly-L-Leu(OEt), Gly-L-Phe(OEt), SarGly(OMe), SarGly(OEt), Sar-L-Ala(OEt), L-ProGly(OEt) and L-Pro-L-Ala(OEt) using the standard N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of I.R., UV-Vis, 1H NMR, 13C NMR, DEPT-135, 1H-13C COSY (HMQC) spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Selected compounds 5, 7, 9, 11, 16, 17 and 18 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.8–8.3 μM.
Synthesis of tetracyanoethylene-substituted ferrocene and its device properties
Kivrak, Arif,Zobi, Cengiz,Torlak, Yasemin,?aml?soy, Ye?im,Ku?, Mahmut,Kivrak, Hilal
, (2018)
Small organic molecules are promising candidates for cheaper, flexible and good-performance sources for organic solar cells (OSCs) due to their easy fabrication, low cost and slightly cheaper processing. However, the lower power conversion efficiency of OSCs is the main problem for their applications. Ferrocene structures could be the best candidates for the active layers of OSCs due to their unique properties such as thermal and chemical stability. The electrochemical, electro-optical and solar cell performances of 2,5-dicyano-3-ferrocenyl-4-ferrocenylethynylhexa-2,4-dienedinitrile (DiCN-Fc) structures were investigated. First, the electrochemical and electro-optical properties were examined for finding the highest occupied and lowest unoccupied molecular orbital values and bandgap of DiCN-Fc. The best photovoltaic performance was obtained with 7?wt% of DiCN-Fc loading, with a power conversion efficiency of about 4.27%. In the light of our investigations, ferrocenyl-substituted small organic molecules could contribute to the development of organic photovoltaic devices.
Novel ferrocene-labeled propargyl amines via CuI multicomponent amination/alkynylation
Srivastava, Suman
, p. 6469 - 6471 (2019)
An efficient synthesis of ferrocene-tagged propargyl amine derivatives via one-pot three-component domino amination/alkynylation in water is reported. The synthesis involves a single Cu(i) catalyst without addition of a ligand, has broad substrate applicability and gives excellent yields.
Synthesis, linear and nonlinear optical properties of thermally stable ferrocene-diketopyrrolopyrrole dyads
Kaur, Sarbjeet,Dhoun, Sugandha,Depotter, Griet,Kaur, Paramjit,Clays, Koen,Singh, Kamaljit
, p. 84643 - 84656 (2015)
A set of new ferrocene-diketopyrrolopyrrole (Fc-DPP) conjugated dyads was synthesized and their optical, nonlinear optical (NLO) and electrochemical properties were investigated. The second-order nonlinear polarizabilities were determined using hyper-Rayleigh scattering with femtosecond pulsed laser light at 840 nm. The dyads exhibited structure dependent NLO response, which could be explained by correlating optical as well as electrochemical data. In the latter case, it is shown that the amplitude of the Fc based one-electron redox process of D-π-A type dyads is doubled in the dyads of the type D-π-A-π-D, where the acceptor (DPP) is flanked by two Fc donors.
Colchicine metallocenyl bioconjugates showing high antiproliferative activities against cancer cell lines
Kowalczyk, Karolina,B?auz, Andrzej,Ciszewski, Wojciech M.,Wieczorek, Anna,Rychlik, B?azej,Plazuk, Damian
, p. 17041 - 17052 (2017)
A series of ferrocenyl and ruthenocenyl conjugates with colchicine bearing a 1,2,3-triazole moiety were synthesized and their anticancer properties were evaluated. We found that the most potent metallocenyl derivatives Rc4 and Rc5 are 6-7 times more cytotoxic toward HepG2 cells, while Fc4 and Fc5 are two times more cytotoxic toward HCT116 cells as colchicine. We also found that compounds Fc4, Fc5, Rc1 and Rc3-Rc5 are able to induce apoptosis, while compound Fc2 arrests mitosis.
Preparation of Bodipy-ferrocene dyads and modulation of the singlet/triplet excited state of bodipy: Via electron transfer and triplet energy transfer
Wu, Xueyan,Wu, Wenting,Cui, Xiaoneng,Zhao, Jianzhang,Wu, Mingbo
, p. 2843 - 2853 (2016)
Modulation of the singlet/triplet excited state of a fluorophore is becoming more important for molecular switches, molecular memory devices, chemical or biological sensors and controllable photodynamic therapy (PDT) etc. Boron-dipyrromethene (Bodipy)-ferrocene (Fc) dyads were prepared for reversible electrochemical switching of the singlet excited state (fluorescence), as well as the triplet excited states of Bodipy. The photophysical properties of the dyads were studied using steady-state UV-vis absorption spectroscopy, fluorescence, electrochemical characterization, time-resolved fluorescence and nanosecond transient absorption spectroscopies. The fluorescence of the Bodipy moieties in the dyads was quenched significantly, due to the photo-induced electron transfer (PET). This conclusion was supported by electrochemical characterization and calculation of the Gibbs free energy changes of PET. We demonstrated that the fluorescence of the Bodipy moiety can be reversibly switched ON and OFF by electrochemical oxidation of the Fc moiety (Fc/Fc+). Furthermore, we proved that the Fc moiety is efficient for quenching of the triplet excited states of Bodipy. Two quenching mechanisms, PET and triplet-triplet-energy transfer (TTET), are responsible for the intramolecular and intermolecular quenching of the triplet excited states of the diiodoBodipy unit.
