Online citations, reference lists, and bibliographies.
← Back to Search

The Electrochemical Grafting Of A Mixture Of Substituted Phenyl Groups At A Glassy Carbon Electrode Surface.

Cyril Louault, M. D'Amours, D. Bélanger
Published 2008 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Two-component substituted aryl groups are simultaneously grafted onto the surface of a glassy carbon electrode by electrochemical reduction of a binary mixture of two aryl diazonium salts in acetonitrile. The electrochemical deposition is achieved potentiostatically and two different mixtures with four different ratios of diazonium salts are used. The binary mixtures comprise: 1) 4-nitrophenyl diazonium and 4-bromophenyl diazonium cations and 2) 4-bromophenyl diazonium and N,N-diethylaniline diazonium cations. The chemical composition of the two component films is determined by cyclic voltammetry in an electrolyte inert for electroactive groups such as nitrophenyl and bromophenyl. X-ray photoelectron spectroscopy is also used to evaluate the surface concentration of each grafted substituted phenyl group. The surface concentration of the substituted phenyl group for which the corresponding diazonium cation is the most easily reduced is higher than its concentration in the mixture of the deposition solution. The usefulness of binary films is also discussed.
This paper references
10.1021/CM0211397
Attachment of Polymers to Organic Moieties Covalently Bonded to Iron Surfaces
A. Adenier (2002)
10.1021/LA00091A013
Wet chemical approaches to the characterization of organic surfaces: self-assembled monolayers, wetting, and the physical-organic chemistry of the solid-liquid interface
G. Whitesides (1990)
10.1021/JA068018I
A structure-reactivity relationship for single walled carbon nanotubes reacting with 4-hydroxybenzene diazonium salt.
N. Nair (2007)
10.1021/JA0383120
Direct covalent grafting of conjugated molecules onto Si, GaAs, and Pd surfaces from aryldiazonium salts.
M. P. Stewart (2004)
10.1021/LA048106L
Time-of-flight secondary ion mass spectroscopy characterization of the covalent bonding between a carbon surface and aryl groups.
C. Combellas (2005)
10.1021/JP962581D
Electrochemical Formation of Close-Packed Phenyl Layers on Si(111)
C. Villeneuve (1997)
10.1021/ED051PA552
Free-radical chemistry (Nonhebel, D.C.)
J. Kochi (1974)
10.1002/1521-4109(200010)12:14<1085::AID-ELAN1085>3.0.CO;2-A
Electrochemically Assisted Covalent Modification of Carbon Electrodes
A. Downard (2000)
10.1021/CM0109903
Highly Functionalized Carbon Nanotubes Using in Situ Generated Diazonium Compounds
Jeffrey L. Bahr and (2001)
10.1021/LA0607510
An interface comprising molecular wires and poly(ethylene glycol) spacer units self-assembled on carbon electrodes for studies of protein electrochemistry.
G. Liu (2006)
10.1021/LA030046G
X-ray photoelectron spectroscopy evidence for the covalent bond between an iron surface and aryl groups attached by the electrochemical reduction of diazonium salts
K. Boukerma (2003)
10.1016/S0022-0728(03)00076-7
Phenyl layers on H/Si(111) by electrochemical reduction of diazonium salts: monolayer versus multilayer formation
P. Allongue (2003)
in Techniques de L’Ing nieur
T. M. Duc (1998)
10.1021/LA063235I
UHV STM I(V) and XPS studies of aryl diazonium molecules assembled on Si(111).
Deepak Pandey (2007)
Possible layers formed upon electrochemical grafting from a mixture of two diazonium salts where R1 and R2 are two different substituents such as NO2
a W. Yang (2005)
10.1021/LA970447U
Selective Replacement of Adsorbed Alkanethiols in Phase-Separated Binary Self-Assembled Monolayers by Electrochemical Partial Desorption
S. Imabayashi (1997)
10.1021/JP046095Z
Multilayer nitroazobenzene films covalently attached to carbon. An AFM and electrochemical study.
P. Brooksby (2005)
10.1021/LA990295Y
Nucleation and Growth of Functionalized Aryl Films on Graphite Electrodes
J. Kariuki (1999)
10.1021/JA0374574
The standard redox potential of the phenyl radical/anion couple.
C. Andrieux (2003)
10.1021/JA00200A039
Formation of monolayers by the coadsorption of thiols on gold: variation in the head group, tail group, and solvent
C. Bain (1989)
10.1021/JA00040A074
Covalent Modification of Carbon Surfaces by Grafting of Functionalized Aryl Radicals Produced from Electrochemical Reduction of Diazonium Salts
M. Delamar (1992)
10.1016/S0022-0728(02)00764-7
Surface dipole formation and non-radiative recombination at p-Si(111) surfaces during electrochemical deposition of organic layers
P. Hartig (2002)
10.1021/LA010415D
Formation of Multilayers on Glassy Carbon Electrodes via the Reduction of Diazonium Salts
J. Kariuki (2001)
10.1021/JP072440J
Time-resolved synchrotron XPS monitoring of irradiation-induced nitrobenzene reduction for chemical lithography.
K. Roodenko (2007)
10.1021/AC9902392
Effects of Surface Monolayers on the Electron-Transfer Kinetics and Adsorption of Methyl Viologen and Phenothiazine Derivatives on Glassy Carbon Electrodes
Hseuh-Hui Yang (1999)
10.1039/B406228K
Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts.
J. Pinson (2005)
10.1021/CM060752D
Direct Modification of a Gold Electrode with Aminophenyl Groups by Electrochemical Reduction of in Situ Generated Aminophenyl Monodiazonium Cations
Joël Lyskawa and (2006)
10.1021/jp027223r
Stability of Substituted Phenyl Groups Electrochemically Grafted at Carbon Electrode Surface.
M. D'Amours (2003)
10.1021/JP054513+
Electrochemical derivatization of carbon surface by reduction of in situ generated diazonium cations.
S. Baranton (2005)
10.1021/LA00031A025
Interchange between monolayers on gold formed from unsymmetrical disulfides and solutions of thiols: evidence for sulfur-sulfur bond cleavage by gold metal
H. Biebuyck (1993)
10.1021/AC034026V
Mono- and multilayer formation by diazonium reduction on carbon surfaces monitored with atomic force microscopy "scratching".
Franklin Anariba (2003)
10.1021/AC026107H
Modified carbon surfaces as "organic electrodes" that exhibit conductance switching.
A. O. Solak (2003)
10.1021/LA053032E
Carbon-fiber microelectrodes modified with 4-sulfobenzene have increased sensitivity and selectivity for catecholamines.
Andre Hermans (2006)
10.1039/B413177K
Electrocatalysis at graphite and carbon nanotube modified electrodes: edge-plane sites and tube ends are the reactive sites.
C. Banks (2005)
10.1021/CM011212D
The Electrochemical Reduction of Diazonium Salts on Iron Electrodes. The Formation of Covalently Bonded Organic Layers and Their Effect on Corrosion
A. Chaussé (2002)
10.1021/LA961033O
Electrochemical Modification of Glassy Carbon Electrode Using Aromatic Diazonium Salts. 1. Blocking Effect of 4-Nitrophenyl and 4-Carboxyphenyl Groups
C. Saby (1997)
10.1021/CM047871I
Functionalization of glassy carbon electrodes with metal-based species
J. Marwan (2005)
10.1021/JA00200A040
Formation of Monolayers by the Coadsorption of Thiols on Gold: Variation in the Length of the Alkyl Chain
C. Bain (1989)
10.1021/LA047369C
Characterization of the deposition of organic molecules at the surface of gold by the electrochemical reduction of aryldiazonium cations.
A. Laforgue (2005)
10.1021/LA010499Q
Barrier Properties of Organic Monolayers on Glassy Carbon Electrodes
Alison J. Downard and (2001)
10.1021/LA701775G
Selective immobilization of DNA and antibody probes on electrode arrays: simultaneous electrochemical detection of DNA and protein on a single platform.
J. Harper (2007)
10.1002/SMLL.200500324
Metal nanoparticles and related materials supported on carbon nanotubes: methods and applications.
G. G. Wildgoose (2006)
10.1021/LA0468848
Nanoscale patterning of flat carbon surfaces by scanning probe lithography and electrochemistry.
P. Brooksby (2005)
10.1016/S0008-6223(97)00010-9
Modification of carbon fiber surfaces by electrochemical reduction of aryl diazonium salts: Application to carbon epoxy composites
M. Delamar (1997)
10.1021/JA00150A024
Reactions of Organic Monolayers on Carbon Surfaces Observed with Unenhanced Raman Spectroscopy
Y. Liu (1995)
10.1021/CM034167D
Organic Layers Bonded to Industrial, Coinage, and Noble Metals through Electrochemical Reduction of Aryldiazonium Salts
M. Bernard (2003)
10.1021/CM060020L
Triazenes as a Stable Diazonium Source for Use in Functionalizing Carbon Nanotubes in Aqueous Suspensions
Jared L. Hudson (2006)
10.1039/B415623D
Nucleophilic and electrophilic displacements on covalently modified carbon: introducing 4,4′-bipyridinium on grafted glassy carbon electrodes
A. H. Holm (2005)
10.1016/J.ELECOM.2007.02.004
Are redox probes a useful indicator of film stability? An electrochemical, AFM and XPS study of electrografted amine films on carbon
Amy C. Cruickshank (2007)
10.1016/J.JELECHEM.2007.06.026
Metallic and bimetallic Cu/Pt species supported on carbon surfaces by means of substituted phenyl groups
Neus Vilà (2007)
10.1016/J.CHEMPHYS.2005.03.033
The modification of glassy carbon and gold electrodes with aryl diazonium salt: The impact of the electrode materials on the rate of heterogeneous electron transfer
Guozhen Liu (2005)
10.1002/ELAN.200403164
High Dispersion and Electrocatalytic Properties of Platinum on Functional Multi‐Walled Carbon Nanotubes
D. Guo (2005)
Possible layers formed upon electrochemical grafting from a mixture of two diazonium salts where R 1 and R 2 are two different substituents such as NO 2 , Br or N ACHTUNGTRENNUNG ( C 2 H 5 )
R. Hitmi (2008)
10.1021/CM0700551
Surface Modification of Conducting Substrates. Existence of Azo Bonds in the Structure of Organic Layers Obtained from Diazonium Salts
P. Doppelt (2007)
10.1149/1.1687428
Covalent Bonding of Organic Molecules to Cu and Al Alloy 2024 T3 Surfaces via Diazonium Ion Reduction
B. Hurley (2004)
10.1021/CM048060H
Electrically Addressable Biomolecular Functionalization of Conductive Nanocrystalline Diamond Thin Films
Wensha Yang (2005)
10.1021/JA963354S
Covalent Modification of Carbon Surfaces by Aryl Radicals Generated from the Electrochemical Reduction of Diazonium Salts
P. Allongue (1997)
10.1021/LA00041A015
Self-assembled monolayers of alkanethiols on gold: comparisons of monolayers containing mixtures of short- and long-chain constituents with methyl and hydroxymethyl terminal groups
J. P. Folkers (1992)
10.1021/JA003276F
Covalent modification of iron surfaces by electrochemical reduction of aryldiazonium salts.
A. Adenier (2001)
10.1021/LA700689B
On-chip chemiluminescent signal enhancement using nanostructured gold-modified carbon microarrays.
B. Corgier (2007)
10.1021/LA061148K
Microscale patterning of organic films on carbon surfaces using electrochemistry and soft lithography.
A. Downard (2006)
10.1016/J.DIAMOND.2005.09.017
Covalent immobilization of glucose oxidase on conducting ultrananocrystalline diamond thin films
J. Wang (2006)
10.1016/S0013-4686(98)00020-6
Organic monolayers on Si(111) by electrochemical method
P. Allongue (1998)
10.1021/LA0629227
Covalent grafting of glassy carbon electrodes with diaryliodonium salts: new aspects.
K. H. Vase (2007)
10.1021/AC052042H
Determination of the structure and orientation of organic molecules tethered to flat graphitic carbon by ATR-FT-IR and Raman spectroscopy.
Franklin Anariba (2006)
10.1021/JA056946W
Diazonium-protein adducts for graphite electrode microarrays modification: direct and addressed electrochemical immobilization.
B. Corgier (2005)
10.1021/JP066868E
Thermal Stability Study of Aryl Modified Carbon Black by in Situ Generated Diazonium Salt
M. Toupin (2007)
10.1016/S0022-0728(98)00252-6
Electrochemical modification of a carbon electrode using aromatic diazonium salts. 2. Electrochemistry of 4-nitrophenyl modified glassy carbon electrodes in aqueous media
B. Ortiz (1998)
10.1016/0022-2860(75)80083-4
Free-Radical Chemistry: Structure and Mechanism
D. C. Nonhebel (1974)



This paper is referenced by
10.1021/la202250y
Design of robust binary film onto carbon surface using diazonium electrochemistry.
Yann R Leroux (2011)
10.1016/j.electacta.2020.136190
Enhanced electrocatalytic activity on TEMPO mixed film grafted by diazonium reduction
M. Cesbron (2020)
Élaboration d'un capteur électrochimique basé sur une interface mixte film de diazonium / nanoparticules d'or pour la détection des traces de mercure(II) dans les eaux naturelles
Fatma Fezai (2019)
10.1016/J.THEOCHEM.2009.02.022
DFT study of electronic properties, structure and spectra of aryl diazonium cations
B. Minaev (2009)
10.1016/J.APSUSC.2016.02.205
Photogeneration of singlet oxygen by the phenothiazine derivatives covalently bound to the surface-modified glassy carbon
Agata Blacha-Grzechnik (2016)
10.1002/9783527650446.CH9
The Use of Aryl Diazonium Salts in the Fabrication of Biosensors and Chemical Sensors
J. Gooding (2012)
10.1016/J.JELECHEM.2016.11.043
Aryldiazonium salt derived mixed organic layers: From surface chemistry to their applications
C. Jiang (2017)
10.1007/s11051-015-3167-2
Diazonium salt-mediated synthesis of new amino, hydroxy, propargyl, and maleinimido-containing superparamagnetic Fe@C nanoparticles as platforms for linking bio-entities or organocatalytic moieties
A. Bunge (2015)
Mechanistic Studies on the Electrochemistry of Proton Coupled Electron Transfer and the Influence of Hydrogen Bonding
T. Alligrant (2010)
10.1016/J.ELECTACTA.2014.01.159
Simultaneous Electroreduction of Different Diazonium Salts for Direct Electrochemical DNA Biosensor Development
L. Hai (2014)
10.1039/d0ob00070a
Use of calixarenes bearing diazonium groups for the development of robust monolayers with unique tailored properties.
L. Troian-Gautier (2020)
10.1016/J.ELECTACTA.2016.01.219
Chloroanthraquinone as a grafted probe molecule to investigate grafting yield on carbon powder
A. L. Comte (2016)
10.1021/ja310889z
Formation of a bifunctional redox system using electrochemical reduction of platinum in ferrocene based ionic liquid and its reactivity with aryldiazonium.
J. Ghilane (2013)
10.1002/ELAN.201200667
Gly-Gly-His Immobilized On Monolayer Modified Back-Side Contact Miniaturized Sensors for Complexation of Copper Ions
Urszula E Wawrzyniak (2013)
10.1002/9783527697489.CH6
Modification of Carbon Electrode Surfaces
M. T. Alam (2015)
10.1002/chem.200901135
Covalent modification of glassy carbon surfaces by using electrochemical and solid-phase synthetic methodologies: application to bi- and trifunctionalisation with different redox centres.
Jean-Mathieu Chrétien (2009)
10.1002/ELAN.200900539
A comparative study of the modification of gold and glassy carbon surfaces with mixed layers of in situ generated aryl diazonium compounds
Guozhen Liu (2010)
10.1021/acs.langmuir.5b04550
Strategies To Achieve Control over the Surface Ratio of Two Different Components on Modified Electrodes Using Aryldiazonium Salts.
C. Jiang (2016)
10.1021/JP5052003
One-Pot Electrografting of Mixed Monolayers with Controlled Composition
L. Santos (2014)
10.1039/c0cs00179a
Aryl diazonium salts: a new class of coupling agents for bonding polymers, biomacromolecules and nanoparticles to surfaces.
Samia Mahouche-Chergui (2011)
Applied Surface Science, 325 (2015) 91-99
T. Darwish (2014)
10.3390/s18020675
Integrated Affinity Biosensing Platforms on Screen-Printed Electrodes Electrografted with Diazonium Salts
P. Yáñez-Sedeño (2018)
10.1002/CELC.201800258
Molecular and Biological Catalysts Coimmobilization on Electrode by Combining Diazonium Electrografting and Sequential Click Chemistry
L. Zhang (2018)
An electrochemical immunobiosensor for dengue virus NS1 protein detection / Nadiya Taha Darwish
Darwish Nadiya Taha (2016)
10.1039/c0cs00139b
The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies.
J. Gooding (2011)
10.1039/d0ta03158e
Hybrid capacitor with anthraquinone-grafted carbon as a battery-type electrode operating in a low pH aqueous salt solution
Emmanuel Pameté Yambou (2020)
10.1016/J.ELECTACTA.2017.05.132
In-situ Raman spectroelectrochemical studies on thionine layer electrochemically grafted to the gold surface
Agata Blacha-Grzechnik (2017)
10.1016/J.SYNTHMET.2015.05.006
Synthesis of conducting azopolymers by electrochemical grafting of a diazonium salt at polypyrrole electrodes
M. Raicopol (2015)
10.1016/J.APSUSC.2014.10.167
Indium tin oxide with zwitterionic interfacial design for biosensing applications in complex matrices
Nadia T. Darwish (2015)
10.1021/la400358e
Using supramolecular binding motifs to provide precise control over the ratio and distribution of species in multiple component films grafted on surfaces: demonstration using electrochemical assembly from aryl diazonium salts.
A. L. Gui (2013)
10.1016/J.ELECTACTA.2010.11.055
Concatenation of electrochemical grafting with chemical or electrochemical modification for preparing electrodes with specific surface functionality
Pallavi Verma (2011)
10.1039/c0cs00149j
Electrografting: a powerful method for surface modification.
D. Bélanger (2011)
See more
Semantic Scholar Logo Some data provided by SemanticScholar