Organic Layers Bonded to Industrial, Coinage, and Noble Metals through Electrochemical Reduction of Aryldiazonium Salts

Bernard, Marie‐Claude; Chaussé, A.; Cabet, Eva; Chehimi, Mohamed M.; Pinson, Jean; Podvorica, Fetah I.; Vautrin-Ul, Christine

doi:10.1021/cm034167d

Cited by 265 publications

(222 citation statements)

References 66 publications

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“…Among them, reduction of diazonium salts can be achieved by either in acetonitrile [8] or aqueous acid solutions [9] and is easily and rapidly carried out in one step, and the reduction method is applicable to a wide variety of aromatic amines many of which are commercially available [10]. The modification of surfaces by electrochemical reduction of diazonium salts can be applied to carbon [11], metals [12] and semiconductors [13]. Additionally, an aromatic amine can be transformed into a diazonium cation by a standard diazotization procedure in an aqueous acidic solution in the presence of NaNO 2 and that the resulting solution can be directly used to modify carbon [14,15] or gold [16] electrode by electrochemical reduction.…”

Section: Introductionmentioning

confidence: 99%

Grafting of phenylboronic acid on a glassy carbon electrode and its application as a reagentless glucose sensor

Morita

Hirayama

Imura

et al. 2011

Journal of Electroanalytical Chemistry

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Phenylboronic acid (PBA) was covalently grafted to the surface of glassy carbon (GC) electrodes using electrochemical reduction of in situ generated diazonium cation. The grafting of GC surfaces was controlled by varying both the concentration of precursor 3-aminophenylboronic acid and the number of potential cycling during the grafting procedure. Cyclic voltammetry (CV) and eletrochemical impedance spectroscopy (EIS) were used to confirm the grafting of the PBA group to the GC surface and formation of multilayer. The barrier properties of the grafted GC electrodes were studied in the presence of a redox probe such as Fe (CN) 3−/4− 6 by CV. Additionally, the resultant PBA multilayer on the GC electrode was applied for glucose detection utilizing the EIS technique in the presence of a redox probe molecule. Then, the complexation ability of the grafted layers with glucose was also confirmed as an increase of total impedance at non-faradic EIS measurement.

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Section: Introductionmentioning

confidence: 99%

Grafting of phenylboronic acid on a glassy carbon electrode and its application as a reagentless glucose sensor

Morita

Hirayama

Imura

et al. 2011

Journal of Electroanalytical Chemistry

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“…This method has been shown by recent reports to be applicable to not only all sorts of carbon materials (graphite, glassy carbon, carbon nanotubes and diamond) [2][3][4], but also metals [5,6], semiconductors [7][8][9][10][11], indium tin oxide and organic materials [12,13]. Using this approach to modify metal surfaces, a range including Fe, Co, Ni, Cu, Zn, Pt and, especially, Au [2,14], has attracted growing interest.…”

Section: Introductionmentioning

confidence: 99%

A Comparative Study of Electrochemical Reduction of 4‐Nitrophenyl Covalently Grafted on Gold and Carbon

et al. 2010

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4-Nitrophenyl layers were grafted on gold and glassy carbon surfaces by electrochemical reductive adsorption of the corresponding diazonium salt. Electrochemical conversion efficiencies of 4-nitrophenyl moieties to 4-aminophenyl moieties on gold versus on glassy carbon in a protic medium were investigated using X-ray photoelectron spectroscopy (XPS). In total contrast to all previous comparative studies showing greater electrochemical reactivity of aryl diazonium salt-derived layers on gold than on glassy carbon, a much lower rate of conversion to 4-aminophenyl was observed on gold than on glassy carbon by both cyclic voltammetry (CV) and chronoamperometry (CA) methods. The lower electron transfer rate during conversion observed on gold versus glassy carbon was proposed to be due to a mechanism related to the molecular structure rearrangement of 4-nitrophenyl during the process on glassy carbon. However, whilst complete conversion of 4-nitrophenyl to 4-aminophenyl on gold by chronoamperometry was achieved, on glassy carbon complete reduction could not be achieved under the same conditions.

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“…This irreversible peak corresponds to formation of a radical, which reacts with the electrode surface to form a covalent metalcarbon bond. 25,28,29 During subsequent cycles, this reduction peak is no longer observed, indicating the formation of a semi-permeable layer on the electrode surface i.e. the grafted diazonium salt forming a thin phenylthiophene film.…”

Section: Resultsmentioning

confidence: 99%

“…[25][26][27] However, the majority of this work was performed on carbon surfaces, and there has been much fewer reports of successful diazonium salt grafting on noble metals. [28][29][30] Herein, we propose the covalent attachment of PEDOT onto Pt and Pt/Ir electrodes using a two-step process, consisting of grafting of (4-thien-2-yl) diazonium salt onto the electrode using electrochemical reduction, followed by electropolymerization of PEDOT (Scheme 1). The electrode surface coverage is measured using the redox chemistry of ferrocene.…”

mentioning

confidence: 99%

Diazonium-Based Anchoring of PEDOT on Pt/Ir Electrodes via Diazonium Chemistry

Chhin

Polcari

Guen

et al. 2018

J. Electrochem. Soc.

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Conducting polymers, specifically poly (3,4-ethylenedioxythiophene) (PEDOT), have recently been coated onto Pt/Ir electrodes intended for neural applications, such as deep brain stimulation (DBS). This modification reduces impedance, increases biocompatibility, and increases electrochemically active surface area. However, direct electropolymerization of PEDOT onto a metallic surface results in physically adsorbed films that suffer from poor adhesion, precluding their use in applications requiring in vivo functionality (i.e. DBS treatment). In this work, we propose a new attachment strategy, whereby PEDOT is covalently attached to an electrode surface through an intermediate phenylthiophene layer, deposited by electrochemical reduction of a diazonium salt. Our electrodes retain their electrochemical performance after more than 1000 redox cycles, whereas physically adsorbed films begin to delaminate after only 40 cycles. Additionally, covalently attached PEDOT maintained strong adhesion even after 10 minutes of ultrasonication (vs. 10 s for physically adsorbed films), confirming its suitability for long-term implantation in the brain. The simple two-step covalent attachment strategy proposed here is particularly useful for neural applications and could also be adapted to introduce other functionalities on the conducting surface.

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Organic Layers Bonded to Industrial, Coinage, and Noble Metals through Electrochemical Reduction of Aryldiazonium Salts

Cited by 265 publications

References 66 publications

Grafting of phenylboronic acid on a glassy carbon electrode and its application as a reagentless glucose sensor

Grafting of phenylboronic acid on a glassy carbon electrode and its application as a reagentless glucose sensor

A Comparative Study of Electrochemical Reduction of 4‐Nitrophenyl Covalently Grafted on Gold and Carbon

Diazonium-Based Anchoring of PEDOT on Pt/Ir Electrodes via Diazonium Chemistry

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