Synthesis and electro-spectroelectrochemistry of ferrocenyl naphthaquinones

Yucel, Baris; Şanlı, Bahar; Soylemez, Huseyin; Yılmaz, İsmail

doi:10.1016/j.tet.2010.12.057

Cited by 14 publications

(23 citation statements)

References 118 publications

(5 reference statements)

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“…The processes are similar to typical CVs of benzoquinone, naphthoquinone, and ferrocene derivatives in aprotic organic solvents without water and acidic ingredients. 4,5,[39][40][41] On the other hand, the electrochemistry of Fc-cnq-1b is similar to that of Fc-cnq-1a under the same conditions ( Figure 2B). Compared to the CVs of Fc-cnq-1a (blue line) and Fc-cnq-1b (red line) in Figure 3, the first reduction potential of Fc-cnq-1a shifted to the cathodic region because of more electron-donating oxygen atoms in case of Fccnq-1a.…”

Section: Mechanistic Aspects Of Ion Pair Formationmentioning

confidence: 94%

“…The 1 Ep and 2 Ep values of Fc-cnq-1a and Fc-cnq-1b showed a good agreement with those of the ferrocenyl naphthoquinones bearing different substituents in the same experimental conditions. 4,5 For the ferrocene molecule, under our experimental conditions, E 1/2 of Fc + /Fc was calculated as E 1/2 = 0.069 V ( E p = 0.085 V) at the scan rate of 0.100 V s −1 , which can be used as a criterion for electrochemical reversibility. 5,[42][43][44] The redox processes of Fc-cnq-1a and Fc-cnq-1b were examined as a function of potential scan rate in order to ascertain the mode of mass transport.…”

Section: Mechanistic Aspects Of Ion Pair Formationmentioning

confidence: 99%

“…The first chemically reversible process at E 1 yields a monoanion radical (semiquinone) product and the second generally at least quasi-reversible process at a more negative potential, E 2 , produces dianion species at customary scan speeds. [1][2][3][4][5] The potentials of these reductions depend on the polarity of solvents, the nature of the supporting electrolyte and the presence of acidic additives, reflecting respectively non-specific solvation energies, ion-pairing and protonation. [1][2][3][4][5] Few studies have been devoted to exploring the ion-pair formation processes between the electrochemically reduced quinones and the cationic species, including some alkali metals and alkaline earth metal cations in aprotic solvents.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3][4][5] The potentials of these reductions depend on the polarity of solvents, the nature of the supporting electrolyte and the presence of acidic additives, reflecting respectively non-specific solvation energies, ion-pairing and protonation. [1][2][3][4][5] Few studies have been devoted to exploring the ion-pair formation processes between the electrochemically reduced quinones and the cationic species, including some alkali metals and alkaline earth metal cations in aprotic solvents. [6][7][8][9] For these studies, some well-known electrochemical methods such as cyclic voltammetry (CV) and pulse-electrolysis stopped-flow were used to explore the mechanistic aspects of the electrochemical reduction of quinones in the presence of metal ions such as Na + , Mg +2 and Ba +2 .…”

Section: Introductionmentioning

confidence: 99%

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Beryllium ion sensing through the ion pair formation between the electrochemically reduced ferrocenyl naphthoquinone radicals and $$\hbox {Be}^{2+}$$ ions

et al. 2019

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We explored the mechanistic aspects of ion pair formation between electrochemically reduced radicals (Fc-cnq-1a • − /Fc-cnq-1b • −) and dianions (Fc-cnq-1a 2− /Fc-cnq-1b 2−) of ferrocenyl naphthoquinones (Fc-cnq-1a and Fc-cnq-1b) and several metal ions by cyclic voltammetry (CV), square wave voltammetry (SWV) and spectroelectrochemistry, for the first time. The experiments demonstrated that Fc-cnq-1a 2− /Fc-cnq-1b 2− were moderately affected with Na + , K + and Cs + by slightly shifting to the anodic side, but were strongly influenced with Li + ion. Fc-cnq-1a • − /Fc-cnq-1b • − were not affected by alkali metal ions, indicating no ion pair formation between the radicals and these ions. Fc-cnq-1a 2− /Fc-cnq-1b 2− was not evolved in the presence of Be 2+ , Mg 2+ and Ca 2+ , but Fc-cnq-1a • − /Fc-cnq-1b • − appeared with their cathodic waves, and participated with intermediates, [(Fc-cnq-1b) 2 • −-Be 2+ and [(Fc-cnq-1a) • −-Cl]. The most pronounced effect on the ion-pair formation of the Fc-cnq-1a • − /Fc-cnq-1b • − was observed in Be 2+ , indicating that Fc-cnq-1a or Fc-cnq-1b can selectively sense ultra-trace amount of Be 2+ (LOD = 3.6 ppb) among the other metal ions with SWV titration, for the first time, based on the strong ion pair formation reaction between the radicals and Be 2+ .

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Section: Mechanistic Aspects Of Ion Pair Formationmentioning

confidence: 94%

Section: Mechanistic Aspects Of Ion Pair Formationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Beryllium ion sensing through the ion pair formation between the electrochemically reduced ferrocenyl naphthoquinone radicals and $$\hbox {Be}^{2+}$$ ions

et al. 2019

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“…The ferrocenyl alcohol (28) was synthesized in two steps starting from ferrocenyl alcohol 2-I (Scheme 9, Eq. (1)).…”

Section: Fementioning

confidence: 99%

Palladium-catalyzed reaction of 2-iodoferrocenyl alcohols with internal alkynes: Synthesis of functionally 1,2-disubstituted ferrocenes and ferroceno-pyrans

Yucel

Şanlı

Soylemez

et al. 2012

Journal of Organometallic Chemistry

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Enantiopure Helical Ferrocene–Triazole–Quinone Triads: Synthesis and Properties

Hoyo

Latorre

Díaz³

et al. 2015

Adv Synth Catal

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The copper(I)‐catalyzed (2+3) cycloaddition between azido (or azidomethylene) ferrocenes and enantiopure (P)‐14‐(p‐ethynylphenyl)‐[5]‐tetrahydro‐helicenequinone afforded ferrocene–triazole–quinone triads, whereas diazido ferrocenes gave rise to the corresponding double triads. In reactions with 1,1′‐diazidoferrocene, the use of CuI/CH3CN or CuSO4/sodium ascorbate/THF conditions allowed the divergent formation of an open chain dimeric structure or a 1,4‐diaza‐[4]‐ferrocenophane resulting from an intramolecular oxidative coupling of the two triazole units formed after the double cycloaddition process.magnified image

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Synthesis and electro-spectroelectrochemistry of ferrocenyl naphthaquinones

Cited by 14 publications

References 118 publications

Beryllium ion sensing through the ion pair formation between the electrochemically reduced ferrocenyl naphthoquinone radicals and $$\hbox {Be}^{2+}$$ ions

Beryllium ion sensing through the ion pair formation between the electrochemically reduced ferrocenyl naphthoquinone radicals and $$\hbox {Be}^{2+}$$ ions

Palladium-catalyzed reaction of 2-iodoferrocenyl alcohols with internal alkynes: Synthesis of functionally 1,2-disubstituted ferrocenes and ferroceno-pyrans

Enantiopure Helical Ferrocene–Triazole–Quinone Triads: Synthesis and Properties

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