Chehimi Aryl Diazonium Salts

New Coupling Agents in Polymer and Surface Science
1. Auflage 2012
ISBN: 978-3-527-65047-7
Verlag: Wiley-VCH
Format: PDF
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, 335 Seiten, E-Book

Diazonium compounds are employed as a new class of coupling agents to link polymers, biomacromolecules, and other species (e. g. metallic nanoparticles) to the surface of materials. The resulting high performance materials show improved chemical and physical properties and find widespread applications. The advantage of aryl diazonium salts compared to other surface modifiers lies in their ease of preparation, rapid (electro)reduction, large choice of reactive functional groups, and strong aryl-surface covalent bonding.

 

This unique book summarizes the current knowledge of the surface and interface chemistry of aryl diazonium salts. It covers fundamental aspects of diazonium chemistry together with theoretical calculations of surface-molecule bonding, analytical methods used for the characterization of aryl layers, as well as important applications in the field of electrochemistry, nanotechnology, biosensors, polymer coatings and materials science. Furthermore, information on other surface modifiers (amines, silanes, hydrazines, iodonium salts) is included. This collection of 14 self-contained chapters constitutes a valuable book for PhD students, academics and industrial researchers working on this hot topic.

Autoren/Hrsg.

Chehimi, Mohamed Mehdi

Inhaltsverzeichnis

Preface

 

ATTACHMENT OF ORGANIC LAYERS TO MATERIALS SURFACES BY REDUCTION OF DIAZONIUM SALTS

A Brief Survey of the Chemistry and Electrochemistry of Diazonium Salts

The Different Methods that Permit Grafting of Diazonium Salts

The Different Substrates, Diazonium Salts, and Solvents that Can Be Used

Evidence for the Presence of a Bond between the Substrate and the Organic Layer

From Monolayers to Multilayers

Structure and Formation of Multilayers

Conclusion

 

ARYL-SURFACE BONDING: A DENSITY FUNCTIONAL THEORY (DFT) SIMULATION APPROACH

Introduction

Density Functional Theory

Bonding between Aryl and Various Substrates

Summary and Outlook

 

PATTERNED MOLECULAR LAYERS ON SURFACES

Methods Based on Scanning Probe Lithography

Methods Based on Soft Lithography

Methods Based on Lithography

Methods Based on Surface-Directed Patterning

Summary and Conclusions

 

ANALYTICAL METHODS FOR THE CHARACTERIZATION OF ARYL LAYERS

Introduction

Scanning Probe Microscopies

UV-VIS Spectroscopy: Transmission, Reflection, and Ellipsometry

IR Spectroscopy

Raman Spectroscopy and Surface-Enhanced Raman Scattering (SERS)

X-ray Photoelectron Spectroscopy (XPS)

X-ray Standing Waves (XSW)

Rutherford Backscattering

Time of Flight Secondary Ion Mass Spectroscopy

Electrochemistry

Contact Angle Measurements

Conclusion

 

MODIFICATION OF NANO-OBJECTS BY ARYL DIAZONIUM SALTS

Introduction

Electrochemical Modification of Nano-objects by Reduction of Diazonium Salts

Chemical Modification of Nano-objects by Reduction of Diazonium Salts

Summary and Conclusions

 

POLYMER GRAFTING TO ARYL DIAZONIUM-MODIFIED MATERIALS: METHODS AND APPLICATIONS

Introduction

Methods for Grafting Coupling Agents from Aryl Diazonium Compounds

Grafting Macromolecules to Surfaces through Aryl Layers

Adhesion of Polymers to Surfaces through Aryl Layers

Conclusion

 

GRAFTING POLYMER FILMS ONTO MATERIAL SURFACES: THE ONE-STEP REDOX PROCESSES

Cathodic Electrografting (CE) in an Organic Medium

Surface Electroinitiated Emulsion Polymerization (SEEP) Chemical Grafting via Chemical Redox Activation (Graftfast/TM)

Summary and Conclusions

 

ELECTROGRAFTING OF CONDUCTIVE OLIGOMERS AND POLYMERS

Introduction

Conjugated Oligomers and Polymers

Surface Grafting Based on Electroreduction of Diazonium Salts

Polyphenylene and Oligophenylene-Tethered Surface Prepared by the Diazonium Reduction of Aniline or 4-Substituted Aniline

n-Doping and Conductance Switching of Grafted Biphenyl, Terphenyl, Nitro-biphenyl and 4-Nitroazobenzene Mono- and Multilayers

p-Doping and Conductance Switching of Grafted Oligo- Phenylthiophene or Oligothiophene Mono- and Multilayers

p-Doping and Conductance Switching of Grafted Oligoaniline Mono- and Multilayers

Conclusion and Outlook

 

THE USE OF ARYL DIAZONIUM SALTS IN THE FABRICATION OF BIOSENSORS AND CHEMICAL SENSORS

Introduction

The Important Features of Aryl Diazonium Salts with Regard to Sensing

Sensors and Biosensors Fabricated Using Aryl Diazonium Salts

Conclusions

 

DIAZONIUM COMPOUNDS IN MOLECULAR ELECTRONICS

Introduction

Fabrication of Molecular Junctions Using Diazonium Reagents Electronic Performance of Diazonium-Derived Molecular Junctions

Summary and Outlook

 

ELECTRONIC PROPERTIES OF SI SURFACES MODIFIED BY ARYL DIAZONIUM COMPOUNDS

Introduction

Experimental Techniques to Characterize Electronic Properties of Si Surfaces in Solutions

Conclusion and Outlook

 

NON-DIAZONIUM ORGANIC AND ORGANOMETALLIC COUPLING AGENTS FOR SURFACE MODIFICATION

Amines

Arylhydrazines

Aryltriazenes

Alcohols

Grignard Reagents

Onium Salts

Alkyl Halides

Conclusion

 

VARIOUS ELECTROCHEMICAL STRATEGIES FOR GRAFTING ELECTRONIC FUNCTIONAL MOLECULES TO SILICON

Introduction

Architecture of Hybrid Devices

Electrografting of Monolayers to Si Negative Differential Resistance Effect in a Monolayer Electrografted Using a Diazonium Complex

Dielectric Monolayers Electrografted Using Silanes

Molecular Diodes Based on C60/Porphyrin-Derivative Bilayers

Über Autor(innen)

Mohamed M. Chehimi is Research Director at the National Center for Scientific Research (CNRS) in France and the leader of the Surface & Interface research group at ITODYS Laboratory of the University Paris Diderot, where he obtained his PhD in physical organic chemistry in 1988 and finished his Habilitation in 1995. He has authored over 200 scientific publications and has received the Honorary Medal from the Polymer Institute (Slovak Academy of Sciences, Slovakia) for long term and efficient international cooperation on surface and interface aspects of nanocomposites in 2008. His main research interests are aryl diazonium coupling agents, reactive and functional ultrathin polymer films via surface polymerization or "click" chemistry, carbon/polymer composites for the uptake of heavy metals, molecularly imprinted polymer-based sensors, clay/polymer nanocomposites and films, powders, latex particles, and nanocomposites of conductive polypyrrole.