Electrochemical kinetic analysis of a 1,4-hydroxynaphthoquinone self-assembled monolayer

March, Grégory; Reisberg, S.; Piro, Benoı̂t; Pham, Minh‐Chau; Delamar, Michel; Noël, Vincent; Odenthal, K.; Hibbert, D. Brynn; Gooding, J. Justin

doi:10.1016/j.jelechem.2008.04.030

Cited by 39 publications

(41 citation statements)

References 47 publications

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“…At a more fundamental level, quinones are currently used, both in solution and immobilised on surfaces, as model systems to understand the electrochemistry of proton coupled electron transfer phenomena [12][13][14][15][16][17][18][19]. Our work takes place in this context, presenting the electrochemical behaviour in buffered and non-buffered conditions of a novel quinone compound, 2,2 0 -dithiobis[ethyl-amino(naphthalene-1,4-dione)], self assembled on gold electrodes.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

Bouffier

Lister

Higgins

et al. 2012

Journal of Electroanalytical Chemistry

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Section: Introductionmentioning

confidence: 99%

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

Bouffier

Lister

Higgins

et al. 2012

Journal of Electroanalytical Chemistry

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“…79 Mechanistic investigation of these hydroxynaphthoquinone SAMs showed that k app was sensitive to pH at around pH 7-9. 80 He et al reported a similar example that probed specific saccharide-protein interaction.…”

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confidence: 99%

The Electrochemical Reaction Mechanism and Applications of Quinones

Kim¹,

Chung²

2014

Bulletin of the Korean Chemical Society

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This tutorial review provides a general account of the electrochemical behavior of quinones and their various applications. Quinone electrochemistry has been investigated for a long time due to its complexity. A simple point of view is developed that considers the relative stability of the reduced quinone species and the values of the first and second reduction potentials. The 9-membered square scheme in buffered aqueous solutions is explained and semiquinone radical stability is discussed in this context. Quinone redox reaction has also been employed in various studies. Diverse examples are presented under three broad categories defined by the roles of quinone: molecular tool for physical chemistry, versatile electron mediator, and charge storage for energy conversion devices.

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“…Quenching of the surface-initiated polymerization at the 1 h time point with vinylferrocene gave a strong surface-bound ferrocene signal in cyclic voltammetry, corresponding to roughly 20% of the maximum theoretical coverage possible for a smooth close-packed monolayer on gold. (Figure 2) Varying the scan rate in the cyclic voltammetry of the pCOT film allows analysis of the kinetics of electron transfer between the electrode and the endgroup via Laviron's formalism 21,22 and the plot of (E a,c -E f ) vs. ln(scan rate), Figure 6. The critical scan rates a and c of the system are determined by extrapolation of the linear portion of the curve to (E a,c -E f ) = 0, and the electron-transfer coefficient is assumed to be 0.5.…”

Section: Resultsmentioning

confidence: 99%

Endgroup and Sidechain Functionalization of Surface-Initiated ROMP Thin Films: Progress Towards ROMP-Based Molecular Wires

Marshall¹

2018

Preprint

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We report functionalized thin films based on endgroup and sidechain modification of polymer films prepared using surface-initiated ring-opening metathesis polymerization (SI-ROMP). Poly(norbornene) can be readily end-functionalized by cross-metathesis with various vinyl chain-transfer agents; however, polyacetylene prepared from cyclooctatetraene (pCOT) is inefficiently end-functionalized (ca. 20% of monolayer surface coverage), while a fused norbornene-teraryl monomer was not successfully endfunctionalized. While these techniques can be used to tune the wettability of a surface or to coat a surface with a thin film of conjugated polymer, efficient "molecular wire" architectures, where a conjugated, intrinsically conducting polymer connects a surface and a molecular species, have still not been constructed using ROMP. We propose a systematic strategy for doing so using the active ester-bearing monomer NbNHS, and demonstrate this strategy's feasibility by preparing SI-ROMP films of poly-NbNHS up to 45 nm in thickness and demonstrating these films' reactivity with a primary amine.

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Electrochemical kinetic analysis of a 1,4-hydroxynaphthoquinone self-assembled monolayer

Cited by 39 publications

References 47 publications

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

The Electrochemical Reaction Mechanism and Applications of Quinones

Endgroup and Sidechain Functionalization of Surface-Initiated ROMP Thin Films: Progress Towards ROMP-Based Molecular Wires

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