Two-Electron, Two-Proton Oxidation of Catechol: Kinetics and Apparent Catalysis

Lin, Qianqi; Li, Qian; Batchelor‐McAuley, Christopher; Compton, Richard G.

doi:10.1021/jp511414b

Cited by 128 publications

(125 citation statements)

References 49 publications

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“…The experimental data gives slopes that are very close to -59 mV per pH unit which is consistent with a 2-electron and 2-proton transfer mechanism at pH values below 9. Similar results have been reported in literature [46,50].…”

Section: Accepted M Manuscriptsupporting

confidence: 93%

“…At pH 10.8 in PBS, the oxidation peak is shifted to more negative potentials, at +0.03V, since the deprotonation step in the scheme of squares is pH dependent [26][27][28]46]. The reduction peak of the ortho-quinone is not observed at slow scan rates and clearly appears only at a scan rate of 200 mV/s, increasing in magnitude at faster scan rates.…”

Section: Accepted M Manuscriptmentioning

confidence: 96%

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Electrochemical reactions of catechol, methylcatechol and dopamine at tetrahedral amorphous carbon (ta-C) thin film electrodes

Palomäki

Chumillas

Sainio

et al. 2015

Diamond and Related Materials

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The electrochemical reactions of dopamine, catechol and methylcatechol were investigated at tetrahedral amorphous carbon (ta-C) thin film electrodes. In order to better understand the reaction mechanisms of these molecules, cyclic voltammetry with varying scan rates was carried out at different pH values in H 2 SO 4 and PBS solutions. The results were compared to the same redox reactions taking place at glassy carbon (GC) electrodes. All three catechols exhibited quasireversible behavior with sluggish electron transfer kinetics at the ta-C electrode. At neutral and alkaline pH, rapid coupled homogeneous reactions followed the oxidation of the catechols to the A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPTcorresponding o-quinones and led to significant deterioration of the electrode response. At acidic pH, the extent of deterioration was considerably lower. All the redox reactions showed significantly faster electron transfer kinetics at the GC electrode and it was less susceptible toward surfacepassivation. An EC mechanism was observed for the oxidation of dopamine at both ta-C and GC electrodes and the formation of polydopamine was suspected to cause the passivation of the electrodes.

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Section: Accepted M Manuscriptsupporting

confidence: 93%

Section: Accepted M Manuscriptmentioning

confidence: 96%

Electrochemical reactions of catechol, methylcatechol and dopamine at tetrahedral amorphous carbon (ta-C) thin film electrodes

Palomäki

Chumillas

Sainio

et al. 2015

Diamond and Related Materials

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show abstract

“…11 The first quasi-reversible wave at E 1/2 = 0.62 V vs the saturated calomel electrode (SCE; 0.24 V vs NHE) arises from a 2e − /2H + Ru IV/II couple at this pH. 16 Oxidation of the Ru(II) form of the complex is accompanied by exchange of …”

Section: Methodsmentioning

confidence: 99%

Electron Transfer Mediator Effects in the Oxidative Activation of a Ruthenium Dicarboxylate Water Oxidation Catalyst

et al. 2015

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The mechanism of electrocatalytic water oxidation by the water oxidation catalyst, ruthenium 2,2′-bipyridine-6,6′-dicarboxylate (bda) bis-isoquinoline (isoq), [Ru(bda)(isoq) 2 ], 1, at metal oxide electrodes has been investigated. At indium-doped tin oxide (ITO), diminished catalytic currents and increased overpotentials are observed compared to glassy carbon (GC). At pH 7.2 in 0.5 M NaClO 4 , catalytic activity is enhanced by the addition of [Ru(bpy) 3 ] 2+ (bpy = bipyridine) as a redox mediator. Enhanced catalytic rates are also observed at ITO electrodes derivatized with the surface-bound phosphonic acid derivative [Ru(4,4′-(PO 3 H 2 ) 2 bpy)(bpy) 2 ] 2+ , RuP 2+ . Controlled potential electrolysis with measurement of O 2 at ITO with and without surface-bound RuP 2+ confirm that water oxidation catalysis occurs. Remarkable rate enhancements are observed with added acetate and phosphate, consistent with an important mechanistic role for atom-proton transfer (APT) in the rate-limiting step as described previously at GC electrodes.

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“…Benzenediols display fascinatingly complex redox chemistry in that they can undergo a reversible two-electron and two-proton oxidation to a quinone ( Figure 112B). 873 While this transformation appears to be a simple conversion of reactant to product, the reversible process involves protoncoupled electron transfer (PCET), where electrons and protons are transferred consecutively or concertedly yielding a number of different pathways and intermediates. The latter are best described by Laviron's scheme of squares, 874 which is shown in Figure 112C for the catechol structure.…”

Section: Special Case Of Benzenediolsmentioning

confidence: 99%

Energy Transfer with Semiconductor Quantum Dot Bioconjugates: A Versatile Platform for Biosensing, Energy Harvesting, and Other Developing Applications

Spillmann²,

et al. 2016

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Luminescent semiconductor quantum dots (QDs) are one of the more popular nanomaterials currently utilized within biological applications. However, what is not widely appreciated is their growing role as versatile energy transfer (ET) donors and acceptors within a similar biological context. The progress made on integrating QDs and ET in biological configurations and applications is reviewed in detail here. The goal is to provide the reader with (1) an appreciation for what QDs are capable of in this context, (2) how this field has grown over a relatively short time span, and, in particular, (3) how QDs are steadily revolutionizing the development of new biosensors along with a myriad of other photonically active nanomaterial-based bioconjugates. An initial discussion of QD materials along with key concepts surrounding their preparation and bioconjugation is provided given the defining role these aspects play in the QDs ability to succeed in subsequent ET applications. The discussion is then divided around the specific roles that QDs provide as either Förster resonance energy transfer (FRET) or charge/electron transfer donor and/or acceptor. For each QD-ET mechanism, a working explanation of the appropriate background theory and formalism is articulated before examining their biosensing and related ET utility. Other configurations such as incorporation of QDs into multistep ET processes or use of initial chemical and bioluminescent excitation are treated similarly. ET processes that are still not fully understood such as QD interactions with gold and other metal nanoparticles along with carbon allotropes are also covered. Given their maturity, some specific applications ranging from in vitro sensing assays to cellular imaging are separated and discussed in more detail. Finally a perspective on how this field will continue to evolve is provided.

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Two-Electron, Two-Proton Oxidation of Catechol: Kinetics and Apparent Catalysis

Cited by 128 publications

References 49 publications

Electrochemical reactions of catechol, methylcatechol and dopamine at tetrahedral amorphous carbon (ta-C) thin film electrodes

Electrochemical reactions of catechol, methylcatechol and dopamine at tetrahedral amorphous carbon (ta-C) thin film electrodes

Electron Transfer Mediator Effects in the Oxidative Activation of a Ruthenium Dicarboxylate Water Oxidation Catalyst

Energy Transfer with Semiconductor Quantum Dot Bioconjugates: A Versatile Platform for Biosensing, Energy Harvesting, and Other Developing Applications

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