Electrochemical characteristics and dyeing properties of selected 9,10-anthraquinones as mediators for the indirect cathodic reduction of dyes

Bechtold, Thomas; Fitz-Binder, Christa; Turcanu, Aurora

doi:10.1016/j.dyepig.2010.03.026

Cited by 25 publications

(9 citation statements)

References 29 publications

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“…This is in good agreement with experimentally obtained E 0 ’ of around −0.7 V NHE,pH=13 for hexahydroxy anthraquinone27. Irrespective of pH, EWGs placed on the edge of the dihydroxylated AQ do not alter E 0 ’.…”

Section: Resultssupporting

confidence: 91%

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Organic Redox Species in Aqueous Flow Batteries: Redox Potentials, Chemical Stability and Solubility

Wedege

Dražević

Kónya

et al. 2016

Sci Rep

260

287

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Organic molecules are currently investigated as redox species for aqueous low-cost redox flow batteries (RFBs). The envisioned features of using organic redox species are low cost and increased flexibility with respect to tailoring redox potential and solubility from molecular engineering of side groups on the organic redox-active species. In this paper 33, mainly quinone-based, compounds are studied experimentially in terms of pH dependent redox potential, solubility and stability, combined with single cell battery RFB tests on selected redox pairs. Data shows that both the solubility and redox potential are determined by the position of the side groups and only to a small extent by the number of side groups. Additionally, the chemical stability and possible degradation mechanisms leading to capacity loss over time are discussed. The main challenge for the development of all-organic RFBs is to identify a redox pair for the positive side with sufficiently high stability and redox potential that enables battery cell potentials above 1 V.

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Section: Resultssupporting

confidence: 91%

“…Crosses indicate literature values1112132627. AQs are found to the left with the sulfonated on top and the hydroxylated in the bottom, while BQs and NQs are found to the right in the top and bottom, respectively.…”

Section: Figurementioning

confidence: 83%

Organic Redox Species in Aqueous Flow Batteries: Redox Potentials, Chemical Stability and Solubility

Wedege

Dražević

Kónya

et al. 2016

Sci Rep

260

287

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show abstract

“…This value is approximately the half value Bechtold et al [25] postulate the direct electro-reduction of the neutral species (AH 2 : several hydroxy-9,10-anthraquinones in ref. [25]) in aqueous basic medium even with a high molar ratio [NaOH]/[ dye] ≈ 200. The voltammetric and spectrophotometric results obtained in our work invalidate the Bechtold proposed mechanism.…”

Section: Effect Of the Added Basementioning

confidence: 83%

“…The electrochemical studies on these dyes have mainly been performed in aqueous solution. Research on adsorption of anthraquinone dyes on hanging mercury drop electrodes [22], electrochemical degradation of anthraquinone dyes [23], electrochemical incineration of dyes [24], the use of 9,10-anthraquinones as mediators for the indirect cathodic reduction of dyes [25], and the electrochemical analysis of natural solid organic dyes and pigments [26] are some examples.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Behaviour of Anthraquinone Dyes in Non Aqueous Solvent Solution.

Caram

Banera

Suárez

et al. 2017

Electrochimica Acta

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The conditions under which alizarin, purpurin, carminc acid, quinalizarin and alizarin red S in the solution of several organic solvents can be electrochemically transformed are analysed. The electrochemical activity of these molecules with quinone and phenolic moieties is relatively easy detected by cyclic voltammetry. Numerous electro-reduction/oxidation processes without and with added acid or base are observed. The number, the current intensity and the peak potential of the charge transfer processes are rationalized on the basis of the homogeneous dissociation equilibriums of the phenolic-OH groups. These equilibria are significantly altered by the medium. A supporting electrolyte unexpected and important effect on the electrochemical behaviour is observed. Alkaline cation of the supporting electrolyte promotes the changes in the electrochemical behaviour by coordinating with opposite charge species. A confusion published in the literature that the electro-reduction of the hydroxyquinones proceeds only through the formation of a radical-anion and a dianion is revealed. Solvent effect is explained by the stabilization of charge species, which is related to some solvent properties (Gutmann acceptor/donor number and dielectric constant). Solvents with strong acceptor properties favour the dissociation of the phenolic-OH groups. The dissociation equilibriums of phenolic-OH groups in each solvent are confirmed by UV-vis spectra of each dye in solution. Alizarin in DMA solvent with added base shows a particular electrochemical behaviour.For alizarin/DMF system a reaction mechanism is proposed, and alternative mechanisms are suggested for other dyes.

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“…It is well known that cyclic voltammetry is a good analytical method for the characterisation of the electrochemical properties of dyes. The electrochemical data are presented in Table .…”

Section: Resultsmentioning

confidence: 99%

6‐Pyridinium benzo[a]phenazine‐5‐oxide derivatives as visible photosensitisers for polymerisation

Podemska

Orzeł

Kowalska

et al. 2014

Coloration Technology

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Several 6‐pyridinium benzo[a]phenazine‐5‐oxide derivatives have been synthesised and characterised by proton nuclear magnetic resonance spectroscopy and mass spectrometry. The spectroscopic and electrochemical properties of these dyes were examined. The dyes were used as reducible sensitisers for selected electron donors (phenylthioacetic acid, phenoxyacetic acid, N‐phenylglycine, and ethyl 4‐N,N‐dimethylaminobenzoate) and as oxidisable sensitisers for electron acceptors (onium and N‐alkoxypyridinium salts). These photoredox pairs were found to be effective visible‐wavelength photoinitiators for the free radical polymerisation of trimethylolpropane triacrylate under visible light. The cationic photopolymerisation of cyclohexene oxide by the studied dyes and the onium salt photoredox pairs was ineffective. The obtained results are discussed on the basis of both free energy change for electron transfer to or from the benzo[a]phenazine dyes and the photochemical properties of the dyes, particularly their photobleaching. The proposed mechanism of dye fading is supported by density functional theory calculations and spectroscopic characterisation of the radical cation of the dye.

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Electrochemical characteristics and dyeing properties of selected 9,10-anthraquinones as mediators for the indirect cathodic reduction of dyes

Cited by 25 publications

References 29 publications

Organic Redox Species in Aqueous Flow Batteries: Redox Potentials, Chemical Stability and Solubility

Organic Redox Species in Aqueous Flow Batteries: Redox Potentials, Chemical Stability and Solubility

Electrochemical Behaviour of Anthraquinone Dyes in Non Aqueous Solvent Solution.

6‐Pyridinium benzo[a]phenazine‐5‐oxide derivatives as visible photosensitisers for polymerisation

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