Novel Method for Grafting Alkyl Chains onto Glassy Carbon. Application to the Easy Immobilization of Ferrocene Used as Redox Probe

Jouikov, Viatcheslav; Simonet, Jacques

doi:10.1021/la204028u

Cited by 50 publications

(66 citation statements)

References 28 publications

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“…its cathodic charge, principally in the interfacial area) is rarely considered or taken into account. A specific charge/discharge process beyond -1.7 V at a Carbone-Lorraine GC macro-electrode helps to interpret the way of trapping primary alkyl iodides [11]. Figure 1A exhibits the charge of such CG electrodes as compared to curves B where a much poorer in (but not void of) C sp2 inclusions GC surface is covered by a thin layer of natural graphite (curve 2).…”

Section: Evidence Of Cathodic Charge Of Carbons At E < -17 Vmentioning

confidence: 99%

Electrochemical conversion of glassy carbon into a poly-nucleophilic reactive material. Applications for carbon chemical functionalization. A mini-review

Jouikov

Simonet²

2014

Electrochemistry Communications

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To cite this version:Viatcheslav Jouikov, Jacques Simonet. Electrochemical conversion of glassy carbon into a polynucleophilic reactive material. Applications for carbon chemical functionalization. A mini-review. Electrochemistry Communications, Elsevier, 2014, 45, pp.32-36 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT AbstractDuring the last decade, various carbon modifications were achieved via radical addition of substituted aryl radicals produced at the surface by chemical or/and electrochemical reduction of corresponding aryldiazonium salts. Very recently, surface reactivity of carbons towards electrophilic halo-derivatives with long alkyl chains had been developed. Surface nucleophilicity of carbons was induced by their specific cathodic charge (at E < -1.7 V in non-aqueous electrolytes) affecting the nano-crystallites (mainly graphite) contained in glassy carbons due to the mode of its manufacturing (high temperature carbonization of phenolic resins). This new paradigm of surface decoration was successfully applied using alkyl halides, carbon dioxide, dioxygen, sulfonyl chlorides etc. and proved efficient with allotropic varieties of carbon (in particular graphites and graphene).

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Section: Evidence Of Cathodic Charge Of Carbons At E < -17 Vmentioning

confidence: 99%

Electrochemical conversion of glassy carbon into a poly-nucleophilic reactive material. Applications for carbon chemical functionalization. A mini-review

Jouikov

Simonet²

2014

Electrochemistry Communications

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“…[1][2][3][4] Glassy carbon (GC), boron doped diamond and graphite have long received attention for electroanalytical and electrocatalytic measurements, [5][6][7][8][9][10][11] and, more recently, carbon nanotubes and graphene have generated considerable interest. [12][13][14][15][16][17] However, despite well-defined bulk properties and structure, carbon materials can possess rather complex surface chemistry that may substantially impact the resulting electrochemistry.…”

Section: Introductionmentioning

confidence: 99%

Molecular Functionalization of Graphite Surfaces: Basal Plane versus Step Edge Electrochemical Activity

et al. 2014

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The chemical functionalization of carbon surfaces has myriad applications, from tailored sensors to electrocatalysts. Here, the adsorption and electrochemistry of anthraquinone-2,6-disulfonate (AQDS) is studied on highly oriented pyrolytic graphite (HOPG) as a model sp 2 surface. A major focus is to elucidate whether adsorbed electroactive AQDS can be used as a marker of step edges, which have generally been regarded as the main electroactive sites on graphite electrode surfaces. First, the macroscopic electrochemistry of AQDS is studied on a range of surfaces differing in step edge density by more than 2 orders of magnitude, complemented with ex-situ tapping mode atomic force microscopy (AFM) data. These measurements show that step edges have little effect on the extent of adsorbed electroactive AQDS. Second, a new fast scan cyclic voltammetry (FSCV) protocol carried out with scanning electrochemical cell microscopy (SECCM) enables the evolution of AQDS adsorption to be followed locally on a rapid timescale. Subsequent AFM imaging of the areas probed by SECCM allows a direct correlation of the electroactive adsorption coverage and the actual step edge density of the entire working area. The amount of adsorbed electroactive AQDS and the electron transfer kinetics are independent of the step edge coverage. Last, SECCM reactive patterning is carried out with complementary AFM measurements, to probe the diffusional electroactivity of AQDS. There is essentially uniform and high activity across the basal surface of HOPG. This work provides new methodology to monitor adsorption processes at surfaces and shows unambiguously that there is no correlation between the step edge density of graphite surfaces and the observed coverage of electroactive AQDS. The electroactivity is dominated by the basal surface, and studies that have used AQDS as a marker of steps need to be revised.3

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“…Macro-modification of graphene were achieved by electrolyses in the presence either of pro-radicals such as {π-acceptor-CH 2 -Br}, often commercially available (Aldrich), or of electrophilic molecules such as substituted organic iodides (the synthesis of Fc-(CH 2 ) 6 -I was previously described [14]) and CO 2 in saturated solutions in the polar organic solvent (DMF or acetonitrile).…”

Section: Methodsmentioning

confidence: 99%

Graphene: Large scale chemical functionalization by cathodic means

Jouikov¹,

Simonet²

2014

Electrochemistry Communications

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Large amounts of graphene were electrochemically functionalized in an adapted frit-separated two-compartment electrolysis cell. The employed technique corresponds to that of a fluidized bed with a dynamic suspension of graphene maintained by an efficient stirring system. A large collector electrode (e.g. a mercury pool or a glassy carbon plate) polarized at a potential adapted to the chemical modification is placed at the center of the cathodic compartment.Modifications are based on two different types of electrochemical reactions: either i) generation of free radicals in situ adding to graphene or ii) the cathodic charge of graphene at the potentials < -1.8 V vs. Ag/AgCl leading to poly-nucleophilic graphene reactive toward electrophilic reagents present in the solution. Several selected examples underline the interest of this method for building modified graphene materials for further use as deposits on different substrates. The mass modification ratio of graphene could be estimated to be quite high, e.g. one COOH group per 100 graphene carbon atoms (ca 35 phenyl units).

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Novel Method for Grafting Alkyl Chains onto Glassy Carbon. Application to the Easy Immobilization of Ferrocene Used as Redox Probe

Cited by 50 publications

References 28 publications

Electrochemical conversion of glassy carbon into a poly-nucleophilic reactive material. Applications for carbon chemical functionalization. A mini-review

Electrochemical conversion of glassy carbon into a poly-nucleophilic reactive material. Applications for carbon chemical functionalization. A mini-review

Molecular Functionalization of Graphite Surfaces: Basal Plane versus Step Edge Electrochemical Activity

Graphene: Large scale chemical functionalization by cathodic means

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