Synthesis, characterisation, electronic spectra and electrochemical investigation of ferrocenyl-terminated dendrimers

Villalonga-Barber, Carolina; Vallianatou, Kalliopi A.; Georgakopoulos, Spyros; Steele, Barry R.; Micha-Screttas, Maria; Levin, Efrat; Lemcoff, N. Gabriel

doi:10.1016/j.tet.2013.03.047

Cited by 12 publications

(8 citation statements)

References 60 publications

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“…The ketones used for the carbinol syntheses were purchased, prepared by literature procedures (vide infra), or prepared by the methods described in the Supporting Information. 1 H NMR (400 MHz), 19 F NMR (376 MHz), and 13 C NMR (101 MHz) spectra were recorded on a Bruker Avance III 400 spectrometer as CD 2 Cl 2 solutions at room temperature or in the solvent indicated. The spectra were referenced to the residual protonated solvent ( 1 H) or the solvent signal ( 13 C).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…This renders ferrocenyl derivatives the most prominent examples of metal–organic tritylium dyes . Vinylogously extended ferrocenyl tritylium cations and dendrimers that absorb in the near-infrared region have also been devised. − In 1979, Nesmeyanov and his co-workers reported ferrocenyl tritylium ions of the type FcC + (Ph)(C 6 H 4 R) (R = OMe, NMe 2 ; Fc = (η 5 -C 5 H 5 )Fe(η 5 -C 5 H 4 ), ferrocenyl) and noted the limited stability and rapid decomposition of the [BPh 4 ] − salt of the methoxy derivative, which precluded the further exploration of its properties . Our group has recently reported the electro- and solvatochromism of similar ferrocenyl diarylmethylium dyes FcC + Ar 2 (Ar = 4-NMe 2 C 6 H 4 , 4-OMeC 6 H 4 ( p -anisyl), 2-Me-4-OMe-C 6 H 3 ) as well as the pentamethylcyclopentadienide congener (η 5 -C 5 Me 5 )Fe(η 5 -C 5 H 4 )C + ( p -anisyl) 2 .…”

Section: Introductionmentioning

confidence: 99%

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4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C⁺Ar₂Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals

et al. 2020

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We report on seven 4-ferrocenylphenyl-substituted tritylium dyes Fc-C 6 H 4 -C + Ar 2 with either unlinked or interlinked aryl residues Ar, including congeners with six-membered (thio)xanthylium and seven-membered (dihydro)dibenzo[a,d]cycloheptatrienylium motifs. All complexes are intensely colored and show more or less intense absorption bands owing to charge transfer from the 4-ferrocenylphenyl donor to the C + Ar 2 acceptor unit as well as reversible electrochromism upon reduction and oxidation. The spectral profiles and redox potentials depend on whether or not the methylium center is incorporated into a 14-πelectron arene system. T-dependent EPR spectroscopy indicates that their one-electron-reduced neutral radicals dimerize. The ensuing monomer−dimer equilibria were studied by quantitative spincounting methods, which revealed an unexpectedly large extent of 85.0−99.6% of dimerization.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C⁺Ar₂Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals

et al. 2020

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“…Villalonga-Barber et al synthesized new dodecaferrocenyl dendrimer 53 using sixfold Huisgen cycloaddition. Each dendron containing four ferrocenyl groups has been synthesized by conventional synthetic methods in good yields [63]. The cyclic voltammetry studies revealed that they all undergo a reversible single-electron transfer process.…”

Section: Ferrocene Derivativesmentioning

confidence: 99%

“…Thus, in most of the cases, polymers are used, Figure 7. Ferrocene dendrimers with nonlinear optical properties [62,63].…”

Section: Fabrication Of Thin Films With Nlo Propertiesmentioning

confidence: 99%

Synthesis and Nonlinear Studies on Selected Organic Compounds in Nanostructured Thin Films

Cinteză¹,

Marinescu²

2018

Advanced Surface Engineering Research

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Organic compounds based on ferrocene, pyrazolone, and octahydroacridine exhibit high interest due to their unusual structure, with potential practical applications due to their special optical properties. Nonlinear optical (NLO) properties of some new synthesized derivatives are evaluated in relationship with the chemical structure by using DFT molecular modeling. In condensed state, ferrocene and other organic molecules were found in a staggered arrangement (D5d) as a nonpolar molecule, but the eclipsed (D5h) and twisted (D5) forms exhibit SHG capabilities. The molecular polarizability (α), first-order hyperpolarizabilities (β tot), dipole (μ tot), and quadrupole (Q) moments were computed. The NLO efficiency was assessed by the relationship between high (β tot)a n dl o wH O M O-L U M O energy gap. The nonlinear optical properties of some new synthesized compounds were evaluated in thin films with nanometric morphology obtained using various methods: Langmuir-Blodgett (LB) thin films, sol-gel deposition, and layer-by-layer deposition.

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“…19,20 Ferrocene has been decorated on the surface of spherical dendrimers of different nature looking for multivalent effects. [21][22][23][24] However, just a few examples have been reported concerning its link to the focal point of dendrons, [25][26][27][28] in which the ferrocene moieties are linked to poly(arylether) or poly(amido amine) dendrons and the study of their anti-cancer activities against AGS cell lines in the latter case. Carbosilane dendrimers have been shown to be effective scaffolds for therapeutic usefulness.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antibacterial behavior of water-soluble carbosilane dendrons containing ferrocene at the focal point

et al. 2015

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A series of novel water-soluble ammonium-terminated carbosilane dendrons containing a ferrocene unit at the focal point were synthesized, in order to combine the unique redox activity of ferrocene and the precisely designed structure of the dendrons with the aim to evaluate them as a new class of potential organometallic-based antibacterial compounds. The synthetic route is based on the initial amination of ferrocenecarboxaldehyde with carbosilane dendrons that contain allyl groups on the surface followed by reduction of the in situ prepared imine product, and the subsequent functionalization of the periphery with terminal amine groups by hydrosilylation reactions. Systems quaternized with HCl are soluble and stable in water or other protic solvents. The obtained compounds were spectrally and electrochemically (cyclic voltammetry) characterized, and diffusion-ordered spectroscopy experiments were conducted to determine the size of the dendritic wedges in solution. The antibacterial activity of these compounds was evaluated using Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli), which shows that the first and second generations of cationic dendrons are broad spectrum antibacterial agents, i.e. selective and effective in both bacterial strains.

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Synthesis, characterisation, electronic spectra and electrochemical investigation of ferrocenyl-terminated dendrimers

Cited by 12 publications

References 60 publications

4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C⁺Ar₂Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals

4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C⁺Ar₂Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals

Synthesis and Nonlinear Studies on Selected Organic Compounds in Nanostructured Thin Films

Synthesis, characterization and antibacterial behavior of water-soluble carbosilane dendrons containing ferrocene at the focal point

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Synthesis, characterisation, electronic spectra and electrochemical investigation of ferrocenyl-terminated dendrimers

Cited by 12 publications

References 60 publications

4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C+Ar2Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals

4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C+Ar2Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals

Synthesis and Nonlinear Studies on Selected Organic Compounds in Nanostructured Thin Films

Synthesis, characterization and antibacterial behavior of water-soluble carbosilane dendrons containing ferrocene at the focal point

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4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C⁺Ar₂Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals

4-Ferrocenylphenyl-Substituted Tritylium Dyes with Open and Interlinked C⁺Ar₂Entities: Redox Behavior, Electrochromism, and a Quantitative Study of the Dimerization of Their Neutral Radicals