Nucleophilic and electrophilic displacements on covalently modified carbon: introducing 4,4′-bipyridinium on grafted glassy carbon electrodes

Holm, Anne I. S.; Møller, Rikke S.; Vase, Karina Højrup; Dong, Mingdong; Norrman, Kion; Besenbacher, Flemming; Pedersen, Steen Uttrup; Daasbjerg, Kim

doi:10.1039/b415623d

Cited by 37 publications

(44 citation statements)

References 38 publications

(53 reference statements)

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“…[1,2] These attachment methods show good reproducibility, and the covalently bonded organic layers produced by them were found to be stable for long-term storage and upon sonication in aggressive solvents. [8] Further chemical modification can be performed on the electrodes through specific substituents (e.g., ÀCOOH, [9] ÀSO 3 H, [9] ÀNMe 2 [9] or À CH 2 Cl [10,11] ) present on the aromatic ring and used to bond metal complexes, [9] enzymes, [12] or as potential supports for combinatorial chemistry. [10] Of particular relevance to our work described here, Pinson, SavØant et al attached both pnitrophenol and p-acetamidophenyl radicals onto a carbon surface using diazonium salts.…”

Section: Introductionmentioning

confidence: 99%

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Chrétien

Ghanem

Bartlett

et al. 2008

Chemistry A European J

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Organic linkers such as (N-Boc-aminomethyl)phenyl (BocNHCH2C6H4) and N-Boc-ethylenediamine (Boc-EDA) have been covalently tethered onto a glassy carbon surface by employing electrochemical reduction of BocNHCH2C6H4 diazonium salt or oxidation of Boc-EDA. After removal of the Boc group, anthraquinone as a redox model was attached to the linker by a solid-phase coupling reaction. Grafting of anthraquinone to electrodes bearing a second spacer such as 4-(N-Boc-aminomethyl)benzoic acid or N-Boc-beta-alanine was also performed by following this methodology. The surface coverage, stability and electron transfer to/from the tethered anthraquinone redox group through the linkers were investigated by cyclic voltammetry. The effects of pH and scan rate were studied, and the electron-transfer coefficient and rate constant were determined by using Laviron's equation for the different types of linker. The combination of electrochemical attachment of protected linkers and subsequent modifications under the conditions of solid-phase synthesis provides a very versatile methodology for tailoring a wide range of organic functional arrangements on a glassy carbon surface.

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Section: Introductionmentioning

confidence: 99%

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Chrétien

Ghanem

Bartlett

et al. 2008

Chemistry A European J

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“…[27,[35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] The main strategy consists of immobilising a 4-nitrophenyl group at the carbon surface by reducing the corresponding diazonium salt, reducing the nitro group to an amine group, then allowing subsequent chemical modifications. [27,35,36,41,43,48,50] Other examples include the immobilisation of a 4-carboxyphenyl group, [39,42,46,47] 4-(chloromethyl)phenyl group, [37,38] 4-(aminoethyl)phenyl group, [40] and more recently phenylmaleimide group, [44] phenylazide or phenylacetylene groups, [45] and boronic acid group, [49] followed by further chemical modification at the reactive groups for the preparation of single modified carbon A C H T U N G T R E N N U N G electrodes.…”

Section: Introductionmentioning

confidence: 99%

Covalent Modification of Glassy Carbon Surfaces by Using Electrochemical and Solid‐Phase Synthetic Methodologies: Application to Bi‐ and Trifunctionalisation with Different Redox Centres

Chrétien

Ghanem

Bartlett

et al. 2009

Chemistry A European J

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Glassy carbon electrodes functionalised with two redox centres have been prepared by using electrochemical and solid-phase synthetic methodologies. Initially the individual coupling of anthraquinone, nitrobenzene and dihydroxybenzene to a glassy carbon electrode bearing an ethylenediamine linker was optimised by using different coupling agents and conditions. Bifunctionalisation was then carried out, either simultaneously, with a mixture of nitrobenzene and dihydroxybenzene, or sequentially, with anthraquinone then nitrobenzene and with anthraquinone then dihydroxybenzene. Characterisation of these electrodes by cyclic voltammetry and differential pulse voltammetry clearly proved the attachment of the pairs of redox centres to the glassy carbon electrode. Their partial surface coverages can be controlled by varying the coupling agent or by controlling the substrate concentration during the solid-phase coupling process. Trifunctionalisation was also realised according to this methodology.

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“…The HOPG surface's step edge can be viewed as a semi-infinite graphene sheet, and its reactivity has been demonstrated by electrochemical experiments [41][42][43][44] and related to the edge state's electronic structure. 38 However, it would be more exciting to explore the chemical reactivity of ZGNRs as we have predicted in this work.…”

Section: Implications For Experimental Studies Of Carbon Materialsmentioning

confidence: 99%

Unique chemical reactivity of a graphene nanoribbon’s zigzag edge

Jiang¹,

Sumpter²,

Dai³

2007

The Journal of Chemical Physics

442

319

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The zigzag edge of a graphene nanoribbon possesses a unique electronic state that is near the Fermi level and localized at the edge carbon atoms. We investigate the chemical reactivity of these zigzag edge sites by examining their reaction energetics with common radicals from first principles. A "partial radical" concept for the edge carbon atoms is introduced to characterize their chemical reactivity, and the validity of this concept is verified by comparing the dissociation energies of edge-radical bonds with similar bonds in molecules. In addition, the uniqueness of the zigzag-edged graphene nanoribbon is further demonstrated by comparing it with other forms of sp 2 carbons, including a graphene sheet, nanotubes, and an armchair-edged graphene nanoribbon.

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Nucleophilic and electrophilic displacements on covalently modified carbon: introducing 4,4′-bipyridinium on grafted glassy carbon electrodes

Cited by 37 publications

References 38 publications

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Covalent Modification of Glassy Carbon Surfaces by Using Electrochemical and Solid‐Phase Synthetic Methodologies: Application to Bi‐ and Trifunctionalisation with Different Redox Centres

Unique chemical reactivity of a graphene nanoribbon’s zigzag edge

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