Dimerization of triphenylamine cation radicals. Evaluation of kinetics using the rotating disk electrode

Marcoux, Lynn; Adams, Ralph N.; Feldberg, Stephen W.

doi:10.1021/j100842a025

Cited by 92 publications

(37 citation statements)

References 2 publications

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“…The anodic oxidation of triphenylamine and its derivatives was extensively studied starting from 1966 [30][31][32][33][34]. As a conclusion of these studies, these oligomers fall in the category of multi-step processes involving electrochemicalchemical-electrochemical (ECE) reactions.…”

Section: Electrochemical Polymerizationmentioning

confidence: 99%

Electrochemical characterization of arylene vinylene oligomers containing triphenylamine and carbazole units

Vacareanu¹,

Grigoraş²

2010

J Appl Electrochem

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Cyclic voltammetry (CV) has been used to investigate the electrochemical behavior of three arylene vinylene oligomers containing triphenylamine and carbazole units at the ends. The synthesis of oligomers was performed using Wittig reaction conditions, between 4-formyltriphenylamine or 3-formyl-N-hexyl-carbazole and two diphosphonium salts. The cyclic voltammograms, recorded in anodic range of potentials, revealed that the oligomers undergo quasi-reversible or irreversible redox processes. Polymer films were deposited on Pt electrode by CV and CPE (Controlled Potential Electrolysis) methods. The polymer films obtained by electrochemical polymerization methods show no solubility in all organic solvents and present similar FT-IR data with those polymers synthesized by chemical oxidative polymerization. Characterizations of the oligomers were made by 1 H-NMR spectroscopy, UV-Vis and fluorescence spectroscopy. Due to the lack of their solubility, the polymers obtained by electrochemical methods were characterized only by FT-IR spectroscopy.

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Section: Electrochemical Polymerizationmentioning

confidence: 99%

Electrochemical characterization of arylene vinylene oligomers containing triphenylamine and carbazole units

Vacareanu¹,

Grigoraş²

2010

J Appl Electrochem

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“…This means that the boundary conditions (8) can be written in a perturbation expansion which yields the coupled system of solutions (10) directly.…”

Section: + E~ -> D (At the Electrode) (Iii) B + C ^ A + D (Throughomentioning

confidence: 99%

ECE versus DISP electrochemical competition

Cole¹,

Wilder²

1989

Quart. Appl. Math.

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Abstract. The ECE (Electrochemical, Chemical, Electrochemical) and DISP (DISProportionation) mechanisms describe electrochemical reactions between four species in a diffusive solution. The general set of reactions which encompass both mechanisms is modelled by:in the case when the applied overpotential is large enough that only the forward steps in (i) and (iii) are present. The ECE mechanism follows the pathway (i), (ii), (iii). The DISP mechanism follows the pathway (i), (ii), (iv). These electrochemical mechanisms play an important role in many organic reactions such as cleavage processes and in inorganic reactions such as the production of forms of technicium used as a radiopharmaceutical. It is important to understand these mechanisms in order to better predict product synthesis and performance. This paper uses asymptotic expansion and perturbation techniques to provide rigorous, relatively simple analytic/numerical solutions for the (linear) ECE mechanism, the (weakly nonlinear) DISP mechanism and a (weakly nonlinear) "competition" mechanism involving all four pathway steps. It is shown that for large dimensionless time, the ECE mechanism evolves to a state with only two species present in order one quantities. Yet, the DISP mechanism retains all four species in order one amounts when step (iv) is reversible. The competition mechanism behaves like the ECE mechanism for small time yet evolves for large time to a form more similar to the DISP mechanism showing that nonlinear effects eventually dominate the mechanistic behavior.

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“…Triarylamines have been the subject of many electrochemical studies [1][2][3][4]. Much attention has been given to the oxidative chemistry of triphenylamine (TPA), in particular its reaction to produce tetraphenylbenzidine [1,2], which has been shown to proceed via the coupling of radical cations.…”

Section: Introductionmentioning

confidence: 99%

“…Much attention has been given to the oxidative chemistry of triphenylamine (TPA), in particular its reaction to produce tetraphenylbenzidine [1,2], which has been shown to proceed via the coupling of radical cations. Recent studies have also revealed intermediate states where the neutral parent TPA stabilises the cation radical TPA þ via the species (TPA) þ n [3,4].…”

Section: Introductionmentioning

confidence: 99%

An electrochemical study of the oxidation of 1,3,5-Tris[4-[(3-methylphenyl)phenylamino]phenyl]benzene

Rees

Wadhawan

Klymenko

et al. 2004

Journal of Electroanalytical Chemistry

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Dimerization of triphenylamine cation radicals. Evaluation of kinetics using the rotating disk electrode

Cited by 92 publications

References 2 publications

Electrochemical characterization of arylene vinylene oligomers containing triphenylamine and carbazole units

Electrochemical characterization of arylene vinylene oligomers containing triphenylamine and carbazole units

ECE versus DISP electrochemical competition

An electrochemical study of the oxidation of 1,3,5-Tris[4-[(3-methylphenyl)phenylamino]phenyl]benzene

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