Method for the electro-addressable functionalization of electrode arrays

Harper, Jason C.; Polsky, Ronen; Dirk, Shawn M.; Wheeler, David R.; Arango, Dulce C.; Brozik, Susan M.

Title: Method for the electro-addressable functionalization of electrode arrays

Abstract

A method for preparing an electrochemical biosensor uses bias-assisted assembly of unreactive -onium molecules on an electrode array followed by post-assembly electro-addressable conversion of the unreactive group to a chemical or biological recognition group. Electro-addressable functionalization of electrode arrays enables the multi-target electrochemical sensing of biological and chemical analytes.

Inventors:: Harper, Jason C.; Polsky, Ronen; Dirk, Shawn M.; Wheeler, David R.; Arango, Dulce C.; Brozik, Susan M.

Issue Date:: 2015-12-15

Research Org.:: Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1229736

Patent Number(s):: 9212430

Application Number:: 11/930,267

Assignee:: Sandia Corporation

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C245/20 - Diazonium compounds

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
C07F5/025 - {Boronic and borinic acid compounds}

C - CHEMISTRY C25 - ELECTROLYTIC OR ELECTROPHORETIC PROCESSES C25D - PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS
C25D9/02 - with organic materials

C - CHEMISTRY C40 - COMBINATORIAL TECHNOLOGY C40B - COMBINATORIAL CHEMISTRY
C40B20/02 - Identifying library members by their fixed physical location on a support or substrate

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DOE Contract Number:: AC04-94AL85000

Resource Type:: Patent

Resource Relation:: Patent File Date: 2007 Oct 31

Country of Publication:: United States

Language:: English

Subject:: 42 ENGINEERING

Citation Formats


                    Harper, Jason C., Polsky, Ronen, Dirk, Shawn M., Wheeler, David R., Arango, Dulce C., and Brozik, Susan M. Method for the electro-addressable functionalization of electrode arrays.  United States: N. p., 2015. 
        Web.

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                    Harper, Jason C., Polsky, Ronen, Dirk, Shawn M., Wheeler, David R., Arango, Dulce C., & Brozik, Susan M. Method for the electro-addressable functionalization of electrode arrays.  United States.

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                    Harper, Jason C., Polsky, Ronen, Dirk, Shawn M., Wheeler, David R., Arango, Dulce C., and Brozik, Susan M. Tue .  
        "Method for the electro-addressable functionalization of electrode arrays".  United States.  https://www.osti.gov/servlets/purl/1229736.

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@article{osti_1229736,

  title        = {Method for the electro-addressable functionalization of electrode arrays},

  author       = {Harper, Jason C. and Polsky, Ronen and Dirk, Shawn M. and Wheeler, David R. and Arango, Dulce C. and Brozik, Susan M.},

  abstractNote = {A method for preparing an electrochemical biosensor uses bias-assisted assembly of unreactive -onium molecules on an electrode array followed by post-assembly electro-addressable conversion of the unreactive group to a chemical or biological recognition group. Electro-addressable functionalization of electrode arrays enables the multi-target electrochemical sensing of biological and chemical analytes.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2015},

  month        = {12}

}

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Zhang, Hong-Xia; Hu, Jin-Song; Yan, Cun-Ji
Physical Chemistry Chemical Physics, Vol. 8, Issue 30
https://doi.org/10.1039/B604587C

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Title: Method for the electro-addressable functionalization of electrode arrays

Abstract

Citation Formats

Voltametric analysis apparatus and method patent, June 1993

Electrochemical affinity assay patent, August 2001

Analytical instruments, biosensors and methods thereof patent, November 2003

Process for derivatizing carbon nanotubes with diazonium species patent, July 2007

Stationary phase deposition based on onium salts patent, January 2008

Electrochemical assembly of organic molecules by the reduction of iodonium salts patent, June 2009

Method for grafting and growing a conductive organic film on a surface patent, June 2010

Electrochemical Method and Sensor for the Detection of Traces of Explosives patent-application, July 2007

Electrochemical detection of nucleic acid hybridization patent-application, January 2010

An Interface Comprising Molecular Wires and Poly(ethylene glycol) Spacer Units Self-Assembled on Carbon Electrodes for Studies of Protein Electrochemistry journal, August 2006

Immobilization of glucose oxidase on a carbon surface derivatized by electrochemical reduction of diazonium salts journal, September 1992

Covalent modification of carbon surfaces by grafting of functionalized aryl radicals produced from electrochemical reduction of diazonium salts journal, July 1992

Biotinylation of Screen-Printed Carbon Electrodes through the Electrochemical Reduction of the Diazonium Salt of p -Aminobenzoyl Biocytin journal, July 1999

Electroaddressable Selective Functionalization of Electrode Arrays: Catalytic NADH Detection Using Aryl Diazonium Modified Gold Electrodes journal, June 2007

Characterization of the Deposition of Organic Molecules at the Surface of Gold by the Electrochemical Reduction of Aryldiazonium Cations journal, July 2005

Electrically Addressable Biomolecular Functionalization of Carbon Nanotube and Carbon Nanofiber Electrodes journal, September 2004

Diazonium salts: Stable monolayers on gold electrodes for sensing applications journal, February 2007

Protein Pattern Assembly by Active Control of a Triblock Copolymer Monolayer journal, December 2006

DNA immobilization onto electrochemically functionalized Si(100) surfaces journal, October 2006

Direct Covalent Grafting of Conjugated Molecules onto Si, GaAs, and Pd Surfaces from Aryldiazonium Salts journal, January 2004

Formation of Polyphenylene Films on Metal Electrodes by Electrochemical Reduction of Benzenediazonium Salts journal, April 2006

Covalent Modification of Carbon Surfaces by Aryl Radicals Generated from the Electrochemical Reduction of Diazonium Salts journal, January 1997

Phenyl layers on H–Si(111) by electrochemical reduction of diazonium salts: monolayer versus multilayer formation journal, July 2003

Mono- and Multilayer Formation by Diazonium Reduction on Carbon Surfaces Monitored with Atomic Force Microscopy “Scratching” journal, August 2003

Organic Layers Bonded to Industrial, Coinage, and Noble Metals through Electrochemical Reduction of Aryldiazonium Salts journal, September 2003

X-ray Photoelectron Spectroscopy Evidence for the Covalent Bond between an Iron Surface and Aryl Groups Attached by the Electrochemical Reduction of Diazonium Salts journal, July 2003

Square wave voltammetric detection of 2,4,6-trinitrotoluene and 2,4-dinitrotoluene on a gold electrode modified with self-assembled monolayers journal, August 2008

Multilayer Nitroazobenzene Films Covalently Attached to Carbon. An AFM and Electrochemical Study journal, May 2005

Nanoscale Patterning of Flat Carbon Surfaces by Scanning Probe Lithography and Electrochemistry journal, March 2005

Parallel dip-pen nanolithography with arrays of individually addressable cantilevers journal, February 2004

Organometallic Chemistry on Silicon and Germanium Surfaces journal, May 2002

Diazonium−Protein Adducts for Graphite Electrode Microarrays Modification: Direct and Addressed Electrochemical Immobilization journal, December 2005

Direct electrochemical addressing of immunoglobulins: Immuno-chip on screen-printed microarray journal, February 2007

Biomolecule immobilization on electrode surfaces by entrapment or attachment to electrochemically polymerized films. A review journal, May 1999

Electrochemical Attachment of Organic Groups to Carbon Felt Surfaces journal, October 2001

Direct electrical communication between chemically modified enzymes and metal electrodes. 2. Methods for bonding electron-transfer relays to glucose oxidase and D-amino-acid oxidase journal, April 1988

Potential-Directed Assembly of Aryl Iodonium Salts onto Silicon {100} Hydride Terminated and Platinum Surfaces journal, November 2005

Microscale Patterning of Organic Films on Carbon Surfaces Using Electrochemistry and Soft Lithography † journal, December 2006

A parallel microfluidic channel fixture fabricated using laser ablated plastic laminates for electrochemical and chemiluminescent biodetection of DNA journal, December 2011

Carbon Electrodes Modified with TiO2/Metal Nanoparticles and Their Application for the Detection of Trinitrotoluene journal, June 2007

Electrografting of Poly(ethylene glycol) Acrylate: A One-Step Strategy for the Synthesis of Protein-Repellent Surfaces journal, August 2005

Indirect Reduction of Aryldiazonium Salts onto Cathodically Activated Platinum Surfaces: Formation of Metal−Organic Structures journal, July 2005

Pt Nanoparticles Functionalized with Nucleic Acid Act as Catalytic Labels for the Chemiluminescent Detection of DNA and Proteins journal, August 2006

The Evolution of Dip-Pen Nanolithography journal, January 2004

A Multifunctional Thin Film Au Electrode Surface Formed by Consecutive Electrochemical Reduction of Aryl Diazonium Salts journal, March 2009

Maleimide-Activated Aryl Diazonium Salts for Electrode Surface Functionalization with Biological and Redox-Active Molecules journal, March 2008

Selective Immobilization of DNA and Antibody Probes on Electrode Arrays: Simultaneous Electrochemical Detection of DNA and Protein on a Single Platform journal, July 2007

Electrochemical Detectors Prepared by Electroless Deposition for Microfabricated Electrophoresis Chips journal, October 2000

Metallic Nanoparticle−Carbon Nanotube Composites for Electrochemical Determination of Explosive Nitroaromatic Compounds journal, August 2006

Covalent Bonding of Organic Molecules to Cu and Al Alloy 2024 T3 Surfaces via Diazonium Ion Reduction journal, January 2004

Nanopatterning of Alkynes on Hydrogen-Terminated Silicon Surfaces by Scanning Probe-Induced Cathodic Electrografting journal, September 2003

Formation of Multilayers on Glassy Carbon Electrodes via the Reduction of Diazonium Salts journal, September 2001

Direct electrochemistry of horseradish peroxidase bonded on a conducting polymer modified glassy carbon electrode journal, November 2003

Scanning Probe Lithography Using Self-Assembled Monolayers journal, November 2003

Electrochemical AFM “Dip-Pen” Nanolithography journal, March 2001

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 journal, December 2005

Raman Spectroscopic Determination of the Structure and Orientation of Organic Monolayers Chemisorbed on Carbon Electrode Surfaces journal, June 1997

Electrografting of Preformed Aliphatic Polyesters onto Metallic Surfaces journal, April 2002

The Electrochemical Grafting of a Mixture of Substituted Phenyl Groups at a Glassy Carbon Electrode Surface journal, June 2008

Simultaneous determination of nitrobenzene and nitro-substituted phenols by differential pulse voltammetry and chemometrics journal, March 2001

Functionalization of Multi-Walled Carbon Nanotubes by Electrografting of Polyacrylonitrile journal, May 2004

Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts journal, January 2005

Diazonium-Functionalized Horseradish Peroxidase Immobilized via Addressable Electrodeposition: Direct Electron Transfer and Electrochemical Detection journal, January 2007

Electrically Addressable Cell Immobilization Using Phenylboronic Acid Diazonium Salts journal, March 2008

Electrically addressable diazonium-functionalized antibodies for multianalyte electrochemical sensor applications journal, January 2008

Multifunctional Electrode Arrays: Towards a Universal Detection Platform journal, March 2008

Nucleic Acid-Functionalized Pt Nanoparticles: Catalytic Labels for the Amplified Electrochemical Detection of Biomolecules journal, April 2006

Reagentless electrochemical immunoassay using electrocatalytic nanoparticle-modified antibodies journal, January 2007

Enzyme Based Amperometric Biosensors for Food Analysis journal, February 2002

Imprinting of Molecular Recognition Sites through Electropolymerization of Functionalized Au Nanoparticles: Development of an Electrochemical TNT Sensor Based on π-Donor−Acceptor Interactions journal, July 2008

Anti-Sticking Effect of Organic Dielectric Formed by Electrodeposition in Microelectromechanical-System Structures journal, July 2005

Sensors—An effective approach for the detection of explosives journal, June 2007

Modified Carbon Surfaces as “Organic Electrodes” That Exhibit Conductance Switching journal, January 2003

Covalent Grafting of Glassy Carbon Electrodes with Diaryliodonium Salts: New Aspects journal, March 2007

Carbon nanotube-modified glassy carbon electrode for adsorptive stripping voltammetric detection of ultratrace levels of 2,4,6-trinitrotoluene journal, February 2004

Electrochemical Sensing of Explosives journal, February 2007

On-line electrochemical monitoring of (TNT) 2,4,6-trinitrotoluene in natural waters journal, June 2003

Voltametric analysis apparatus and method
patent, June 1993

Electrochemical affinity assay
patent, August 2001

Analytical instruments, biosensors and methods thereof
patent, November 2003

Process for derivatizing carbon nanotubes with diazonium species
patent, July 2007

Stationary phase deposition based on onium salts
patent, January 2008

Electrochemical assembly of organic molecules by the reduction of iodonium salts
patent, June 2009

Method for grafting and growing a conductive organic film on a surface
patent, June 2010

Electrochemical Method and Sensor for the Detection of Traces of Explosives
patent-application, July 2007

Electrochemical detection of nucleic acid hybridization
patent-application, January 2010

An Interface Comprising Molecular Wires and Poly(ethylene glycol) Spacer Units Self-Assembled on Carbon Electrodes for Studies of Protein Electrochemistry
journal, August 2006

Immobilization of glucose oxidase on a carbon surface derivatized by electrochemical reduction of diazonium salts
journal, September 1992

Covalent modification of carbon surfaces by grafting of functionalized aryl radicals produced from electrochemical reduction of diazonium salts
journal, July 1992

Biotinylation of Screen-Printed Carbon Electrodes through the Electrochemical Reduction of the Diazonium Salt of p -Aminobenzoyl Biocytin
journal, July 1999

Electroaddressable Selective Functionalization of Electrode Arrays: Catalytic NADH Detection Using Aryl Diazonium Modified Gold Electrodes
journal, June 2007

Characterization of the Deposition of Organic Molecules at the Surface of Gold by the Electrochemical Reduction of Aryldiazonium Cations
journal, July 2005

Electrically Addressable Biomolecular Functionalization of Carbon Nanotube and Carbon Nanofiber Electrodes
journal, September 2004

Diazonium salts: Stable monolayers on gold electrodes for sensing applications
journal, February 2007

Protein Pattern Assembly by Active Control of a Triblock Copolymer Monolayer
journal, December 2006

DNA immobilization onto electrochemically functionalized Si(100) surfaces
journal, October 2006

Direct Covalent Grafting of Conjugated Molecules onto Si, GaAs, and Pd Surfaces from Aryldiazonium Salts
journal, January 2004

Formation of Polyphenylene Films on Metal Electrodes by Electrochemical Reduction of Benzenediazonium Salts
journal, April 2006

Covalent Modification of Carbon Surfaces by Aryl Radicals Generated from the Electrochemical Reduction of Diazonium Salts
journal, January 1997

Phenyl layers on H–Si(111) by electrochemical reduction of diazonium salts: monolayer versus multilayer formation
journal, July 2003

Mono- and Multilayer Formation by Diazonium Reduction on Carbon Surfaces Monitored with Atomic Force Microscopy “Scratching”
journal, August 2003

Organic Layers Bonded to Industrial, Coinage, and Noble Metals through Electrochemical Reduction of Aryldiazonium Salts
journal, September 2003

X-ray Photoelectron Spectroscopy Evidence for the Covalent Bond between an Iron Surface and Aryl Groups Attached by the Electrochemical Reduction of Diazonium Salts
journal, July 2003

Square wave voltammetric detection of 2,4,6-trinitrotoluene and 2,4-dinitrotoluene on a gold electrode modified with self-assembled monolayers
journal, August 2008

Multilayer Nitroazobenzene Films Covalently Attached to Carbon. An AFM and Electrochemical Study
journal, May 2005

Nanoscale Patterning of Flat Carbon Surfaces by Scanning Probe Lithography and Electrochemistry
journal, March 2005

Parallel dip-pen nanolithography with arrays of individually addressable cantilevers
journal, February 2004

Organometallic Chemistry on Silicon and Germanium Surfaces
journal, May 2002

Diazonium−Protein Adducts for Graphite Electrode Microarrays Modification: Direct and Addressed Electrochemical Immobilization
journal, December 2005

Direct electrochemical addressing of immunoglobulins: Immuno-chip on screen-printed microarray
journal, February 2007

Biomolecule immobilization on electrode surfaces by entrapment or attachment to electrochemically polymerized films. A review
journal, May 1999

Electrochemical Attachment of Organic Groups to Carbon Felt Surfaces
journal, October 2001

Direct electrical communication between chemically modified enzymes and metal electrodes. 2. Methods for bonding electron-transfer relays to glucose oxidase and D-amino-acid oxidase
journal, April 1988

Potential-Directed Assembly of Aryl Iodonium Salts onto Silicon {100} Hydride Terminated and Platinum Surfaces
journal, November 2005

Microscale Patterning of Organic Films on Carbon Surfaces Using Electrochemistry and Soft Lithography ^†
journal, December 2006

A parallel microfluidic channel fixture fabricated using laser ablated plastic laminates for electrochemical and chemiluminescent biodetection of DNA
journal, December 2011

Carbon Electrodes Modified with TiO₂/Metal Nanoparticles and Their Application for the Detection of Trinitrotoluene
journal, June 2007

Electrografting of Poly(ethylene glycol) Acrylate: A One-Step Strategy for the Synthesis of Protein-Repellent Surfaces
journal, August 2005

Indirect Reduction of Aryldiazonium Salts onto Cathodically Activated Platinum Surfaces: Formation of Metal−Organic Structures
journal, July 2005

Pt Nanoparticles Functionalized with Nucleic Acid Act as Catalytic Labels for the Chemiluminescent Detection of DNA and Proteins
journal, August 2006

The Evolution of Dip-Pen Nanolithography
journal, January 2004

A Multifunctional Thin Film Au Electrode Surface Formed by Consecutive Electrochemical Reduction of Aryl Diazonium Salts
journal, March 2009

Maleimide-Activated Aryl Diazonium Salts for Electrode Surface Functionalization with Biological and Redox-Active Molecules
journal, March 2008

Selective Immobilization of DNA and Antibody Probes on Electrode Arrays: Simultaneous Electrochemical Detection of DNA and Protein on a Single Platform
journal, July 2007

Electrochemical Detectors Prepared by Electroless Deposition for Microfabricated Electrophoresis Chips
journal, October 2000

Metallic Nanoparticle−Carbon Nanotube Composites for Electrochemical Determination of Explosive Nitroaromatic Compounds
journal, August 2006

Covalent Bonding of Organic Molecules to Cu and Al Alloy 2024 T3 Surfaces via Diazonium Ion Reduction
journal, January 2004

Nanopatterning of Alkynes on Hydrogen-Terminated Silicon Surfaces by Scanning Probe-Induced Cathodic Electrografting
journal, September 2003

Formation of Multilayers on Glassy Carbon Electrodes via the Reduction of Diazonium Salts
journal, September 2001

Direct electrochemistry of horseradish peroxidase bonded on a conducting polymer modified glassy carbon electrode
journal, November 2003

Scanning Probe Lithography Using Self-Assembled Monolayers
journal, November 2003

Electrochemical AFM “Dip-Pen” Nanolithography
journal, March 2001

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
journal, December 2005

Raman Spectroscopic Determination of the Structure and Orientation of Organic Monolayers Chemisorbed on Carbon Electrode Surfaces
journal, June 1997

Electrografting of Preformed Aliphatic Polyesters onto Metallic Surfaces
journal, April 2002

The Electrochemical Grafting of a Mixture of Substituted Phenyl Groups at a Glassy Carbon Electrode Surface
journal, June 2008

Simultaneous determination of nitrobenzene and nitro-substituted phenols by differential pulse voltammetry and chemometrics
journal, March 2001

Functionalization of Multi-Walled Carbon Nanotubes by Electrografting of Polyacrylonitrile
journal, May 2004

Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts
journal, January 2005

Diazonium-Functionalized Horseradish Peroxidase Immobilized via Addressable Electrodeposition: Direct Electron Transfer and Electrochemical Detection
journal, January 2007

Electrically Addressable Cell Immobilization Using Phenylboronic Acid Diazonium Salts
journal, March 2008

Electrically addressable diazonium-functionalized antibodies for multianalyte electrochemical sensor applications
journal, January 2008

Multifunctional Electrode Arrays: Towards a Universal Detection Platform
journal, March 2008

Nucleic Acid-Functionalized Pt Nanoparticles: Catalytic Labels for the Amplified Electrochemical Detection of Biomolecules
journal, April 2006

Reagentless electrochemical immunoassay using electrocatalytic nanoparticle-modified antibodies
journal, January 2007

Enzyme Based Amperometric Biosensors for Food Analysis
journal, February 2002

Imprinting of Molecular Recognition Sites through Electropolymerization of Functionalized Au Nanoparticles: Development of an Electrochemical TNT Sensor Based on π-Donor−Acceptor Interactions
journal, July 2008

Anti-Sticking Effect of Organic Dielectric Formed by Electrodeposition in Microelectromechanical-System Structures
journal, July 2005

Sensors—An effective approach for the detection of explosives
journal, June 2007

Modified Carbon Surfaces as “Organic Electrodes” That Exhibit Conductance Switching
journal, January 2003

Covalent Grafting of Glassy Carbon Electrodes with Diaryliodonium Salts: New Aspects
journal, March 2007

Carbon nanotube-modified glassy carbon electrode for adsorptive stripping voltammetric detection of ultratrace levels of 2,4,6-trinitrotoluene
journal, February 2004

Electrochemical Sensing of Explosives
journal, February 2007

On-line electrochemical monitoring of (TNT) 2,4,6-trinitrotoluene in natural waters
journal, June 2003

Real-Time Electrochemical Monitoring: Toward Green Analytical Chemistry
journal, September 2002

Screen-printed voltammetric sensor for TNT
journal, August 1998

Single-Channel Microchip for Fast Screening and Detailed Identification of Nitroaromatic Explosives or Organophosphate Nerve Agents
journal, March 2002