Electrochemical reactions with protonations at equilibrium

Laviron, E.; Roullier, L.

doi:10.1016/s0022-0728(83)80372-6

Cited by 45 publications

(30 citation statements)

References 28 publications

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“…They are structural analogues to anthraquinones and their reduction mechanism also depends on the media, occurring either via a 2-electron reduction (ET) in two steps in aprotic solvents, or via a 2e À /2H + proton-coupled electron transfer (PCET) mechanism in a single step in protic media. [31][32][33] Moreover, similar to quinones, some properties of phenazines such as their redox potential strongly depend on the nature of functional groups in the molecular structure. 34 However, there are only a few examples where phenazine compounds have been used for redox ow batteries.…”

Section: Introductionmentioning

confidence: 99%

New insights into phenazine-based organic redox flow batteries by using high-throughput DFT modelling

Cruz

Molina

Patil

et al. 2020

Sustainable Energy Fuels

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Section: Introductionmentioning

confidence: 99%

New insights into phenazine-based organic redox flow batteries by using high-throughput DFT modelling

Cruz

Molina

Patil

et al. 2020

Sustainable Energy Fuels

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“…20,21 The electrochemical polymerization of phenazine derivatives and the effect of pH on rate constant of phenazines have also been documented in literature. 22,23 The electrochemical polymerization of phenazines depends not only on applied potential but also on the pH of the of the medium.…”

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confidence: 99%

pH Dependent Electrochemical Characterization, Computational Studies and Evaluation of Thermodynamic, Kinetic and Analytical Parameters of Two Phenazines

Shah

Zaid

Shah

et al. 2014

J. Electrochem. Soc.

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The electrochemical response of two biologically important phenazine derivatives was examined by using cyclic, differential pulse and square wave voltammetry in a wide pH range of 2.0 -12.0. Cyclic voltammetry was employed for the determination of heterogeneous electron transfer rate constant and diffusion coefficient of the analytes. The value of electron transfer rate constant was used for evaluation of Gibbs free energy, enthalpy and entropy changes of redox reactions of the compounds. Differential pulse voltammetry was used for the determination of number of protons and electrons involved in the redox processes. Limits of detection and quantification were assessed by square wave voltammetry. The detailed pH dependent redox mechanisms of the compounds were proposed on the basis of experimental results which were further supported by theoretical calculations. These redox mechanistic pathways are expected to play a key role in understanding the necessary aspects of structure-activity relationships and exploring the hidden routes by which this class of compounds exert its biochemical actions. Phenazines have broad range applications in biology and chemistry.1 This class constitutes a large group of nitrogen containing heterocyclic compounds, the members of which differ in their chemical and physical properties on the basis of type and position of functional groups present. Naturally, phenazines are produced by limited genera of bacteria including Pseudomonas, Burkholderia and Brevibacterium.2 Starting from different parent materials, phenazines can be synthesized by various reactions including oxidative condensation, electrochemical reduction, reductive cyclization and photochemical reactions.From the last 50 years, phenazines are the subject of extensive research investigations because of their broad range applications in pharmaceutical and clinical research.3 Such compounds have been reported for their wide variety of biological activities such as antitumor, anti-parasitic and antibiotic activities. Benzo [a] phenazine acts as efficient DNA intercalating ligand with antitumor activity in leukaemia and solid tumors. 4 1-Hydroxyphenazine has been reported to have promising antifungal activity against various microbes such as aspergillus fumigatus and candida albicans.5 Macrolactone synthesized from benzo [a] phenazine shows good activity against mycobacterium tuberculosis. 6 In general, natural and synthetic phenazines find useful applications against malaria 7 and hepatitis C viral replication. 8The biological activity of phenazines is due to their redox reactions leading to the formation of toxic radicals. 9 Different functional groups attached to phenazine determine their redox potential and solubility. The redox behavior and concomitant modulation of biological activities of phenazines by changing the nature and position of substituents attached to their aromatic rings have been reported by several research groups.10-12 Phenazines can alter cellular redox states and act as transporters of electrons to altern...

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“…Moreover, the analysis of the peaks intensity shows a reversible electrochemical behavior with a value of I a /I c ¼0.96. The calculation of the E FWHM ¼86 mV which is below the theoretical value of 90.6 mV defines a nerstian monoelectronic process strongly adsorbed on the electrode surface (Laviron, 1982). The surface coverage of electroactive MPA-cyt c on gold was estimated to be G¼4 Â 10 -12 mol cm À 2 which corresponds roughly to 25% of the theoretical value reported by Nakano et al (2007) for a fully packed cyt c surface coverage.…”

Section: Resultsmentioning

confidence: 71%

Biosensor based on chemically-designed anchorable cytochrome c for the detection of H2O2 released by aquaticcells

Suárez¹,

Santschi²,

Martin³

et al. 2013

Biosensors and Bioelectronics

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a b s t r a c tA novel third generation biosensor was developed based on one-shot adsorption of chemicallymodified cytochrome c (cyt c) onto bare gold electrodes. In contrast to the classic approach which consists of attaching cyt c onto an active self-assembled monolayer (SAM) priory chemisorbed on gold, here short-chain thiol derivatives (mercaptopropionic acid, MPA) were chemically introduced on cyt c protein shell via its lysine residues enabling the very fast formation (o 5 min) of an electroactive biological self-assembled monolayer (SAM) exhibiting a quasi-reversible electrochemical behavior and a fast direct electron transfer (ET). The heterogeneous ET rate constant was estimated to be k s ¼ 1600 s, confirming that short anchors facilitate the ET via an efficient orientation of the heme pocket. In comparison, no ET was observed in the case of native and long-anchor (mercaptoundecanoic acid, MUA) modified cyt c directly adsorbed on gold. However, in both cases the ET was efficiently restored upon in-bulk generation of gold nanoparticles which acted as electron shuttles. This observation emphasizes that the lack of electroactivity might be caused by either an inappropriate orientation of the protein (native cyt c) or a critical distance (MUA-cyt c). Finally, the sensitivity of the bare gold electrode directly modified with MPA-cyt c to hydrogen peroxide (H 2 O 2 ) was evaluated by amperometry and the so-made amperometric biosensor was able to perform real-time and noninvasive detection of endogeneous H 2 O 2 released by unicellular aquatic microorganisms, Chlamydomonas reinhardtii, upon cadmium exposure.

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Electrochemical reactions with protonations at equilibrium

Cited by 45 publications

References 28 publications

New insights into phenazine-based organic redox flow batteries by using high-throughput DFT modelling

New insights into phenazine-based organic redox flow batteries by using high-throughput DFT modelling

pH Dependent Electrochemical Characterization, Computational Studies and Evaluation of Thermodynamic, Kinetic and Analytical Parameters of Two Phenazines

Biosensor based on chemically-designed anchorable cytochrome c for the detection of H2O2 released by aquaticcells

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