CiNii Books - Aryl diazonium salts : new coupling agents in polymer and surface science

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.

Table of Contents

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 Memory Effect in TPP-C11 Monolayers Electrografted Using a C=C Linker Summary PATENTS AND INDUSTRIAL APPLICATIONS OF ARYL DIAZONIUM SALTS AND OTHER COUPLING AGENTS Introduction Patents Industrial Applications Conclusion

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Aryl diazonium salts : new coupling agents in polymer and surface science

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