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E-grāmata: Aryl Diazonium Salts - New Coupling Agents and Surafec Science: New Coupling Agents in Polymer and Surface Science [Wiley Online]

Edited by (Université Paris Diderot,)
  • Formāts: 356 pages
  • Izdošanas datums: 06-Jun-2012
  • Izdevniecība: Blackwell Verlag GmbH
  • ISBN-10: 352765044X
  • ISBN-13: 9783527650446
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  • Wiley Online
  • Cena: 208,80 €*
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Aryl Diazonium Salts - New Coupling Agents and Surafec Science: New Coupling Agents in Polymer and Surface SciencePalielināt
  • Formāts: 356 pages
  • Izdošanas datums: 06-Jun-2012
  • Izdevniecība: Blackwell Verlag GmbH
  • ISBN-10: 352765044X
  • ISBN-13: 9783527650446
Citas grāmatas par šo tēmu:
Wiley Online E-booksMore info about Wiley Online
Rokasgrāmatas mājas lapa: https://onlinelibrary.wiley.com/doi/book/10.1002/9783527650446
The salts are used in the synthesis of a large series of organic compounds, so much has been written about them. However, there has been little study of their surface and intersurface chemistry despite the growing interest in surface chemistry generally. Here, chemists and related scientists begin to fill that gap by exploring such aspects as attaching organic layers to material surfaces by reducing diazonium salts, analytical methods for characterizing aryl layers, electrografting conductive oligomers and polymers, electronic properties of silicon surfaces modified by aryl diazonium compounds, and various electrochemical strategies for grafting electronic functional molecules to silicon. Annotation ©2012 Book News, Inc., Portland, OR (booknews.com)

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.
Preface xv
List of Contributors
xvii
1 Attachment of Organic Layers to Materials Surfaces by Reduction of Diazonium Salts
1(36)
Jean Pinson
1.1 A Brief Survey of the Chemistry and Electrochemistry of Diazonium Salts
1(2)
1.2 The Different Methods that Permit Grafting of Diazonium Salts
3(4)
1.2.1 Electrochemistry
3(1)
1.2.2 Reducing Substrate, Homolytic Dediazonation, Reaction with the Substrate
4(1)
1.2.3 Reducing Reagent
5(1)
1.2.4 Neutral and Basic Media
6(1)
1.2.5 Ultrasonication
6(1)
1.2.6 Heating and Microwave
6(1)
1.2.7 Mechanical Grafting
7(1)
1.2.8 Photochemistry
7(1)
1.3 The Different Substrates, Diazonium Salts, and Solvents that Can Be Used
7(4)
1.3.1 Substrates
7(2)
1.3.2 Diazonium Salts
9(1)
1.3.3 Solvents
10(1)
1.4 Evidence for the Presence of a Bond between the Substrate and the Organic Layer
11(2)
1.4.1 Stability of the Layer
11(1)
1.4.2 Spectroscopic Evidence for a Bond
12(1)
1.5 From Monolayers to Multilayers
13(8)
1.5.1 Monolayers
14(2)
1.5.2 Layers of Medium Thickness
16(3)
1.5.2.1 Thick Layers
19(2)
1.6 Structure and Formation of Multilayers
21(6)
1.6.1 Chemical Structure
21(1)
1.6.2 The Spatial Structure of the Layers
22(1)
1.6.3 Compactness of the Layers
23(1)
1.6.4 Swelling of the Layer
24(1)
1.6.5 Electron Transfer through the Layers
24(1)
1.6.6 The Formation Mechanism of Multilayers
25(2)
1.7 Conclusion
27(10)
References
27(10)
2 Aryl-Surface Bonding: A Density Functional Theory (DFT) Simulation Approach
37(16)
Nan Shao
Sheng Dai
De-en Jiang
2.1 Introduction
37(1)
2.2 Density Functional Theory
38(1)
2.3 Bonding between Aryl and Various Substrates
38(10)
2.3.1 On Graphite/Graphene
39(1)
2.3.1.1 On the Basal Plane
39(3)
2.3.1.2 On the Edges of Graphene
42(2)
2.3.2 On Carbon Nanotubes
44(1)
2.3.3 On Metal Surfaces
45(3)
2.4 Summary and Outlook
48(5)
Acknowledgments
49(1)
References
50(3)
3 Patterned Molecular Layers on Surfaces
53(18)
Alison J. Downard
Andrew J. Cross
Bradley M. Simons
3.1 Methods Based on Scanning Probe Lithography
53(4)
3.1.1 AFM
54(1)
3.1.2 SECM
54(2)
3.1.3 Spotting
56(1)
3.2 Methods Based on Soft Lithography
57(3)
3.2.1 Printing
57(2)
3.2.2 Molds
59(1)
3.2.3 Nanosphere Lithography
59(1)
3.3 Methods Based on Lithography
60(2)
3.4 Methods Based on Surface-Directed Patterning
62(4)
3.4.1 Modification of Si Surfaces
63(1)
3.4.2 Modified Electrode Arrays
64(2)
3.5 Summary and Conclusions
66(5)
References
68(3)
4 Analytical Methods for the Characterization of Aryl Layers
71(32)
Karsten Hinrichs
Katy Roodenko
Jorg Rappich
Mohamed M. Chehimi
Jean Pinson
4.1 Introduction
71(1)
4.2 Scanning Probe Microscopies
71(1)
4.3 UV--VIS Spectroscopy: Transmission, Reflection, and Ellipsometry
72(1)
4.4 IR Spectroscopy
72(11)
4.4.1 Transmission Spectroscopy
73(1)
4.4.2 Reflection Spectroscopy
74(1)
4.4.3 Infrared Spectroscopic Ellipsometry (IRSE)
75(2)
4.4.4 IRSE Surface Characterization
77(2)
4.4.5 In Situ IR Spectroscopy: ATR and IRSE
79(4)
4.5 Raman Spectroscopy and Surface-Enhanced Raman Scattering (SERS)
83(1)
4.6 X-ray Photoelectron Spectroscopy (XPS)
84(7)
4.7 X-ray Standing Waves (XSW)
91(2)
4.8 Rutherford Backscattering
93(1)
4.9 Time of Flight Secondary Ion Mass Spectroscopy
93(1)
4.10 Electrochemistry
94(2)
4.11 Contact Angle Measurements
96(1)
4.12 Conclusion
96(7)
References
98(5)
5 Modification of Nano-objects by Aryl Diazonium Salts
103(22)
Dao-Jun Cuo
Fakhradin Mirkhalaf
5.1 Introduction
103(2)
5.2 Electrochemical Modification of Nano-objects by Reduction of Diazonium Salts
105(7)
5.2.1 Surface Modification of Carbon Nano-objects via Electrochemical Reduction of Aryl Diazonium Cations
105(6)
5.2.2 Surface Modification of Metal and Metal Oxide Nano-objects via Electrochemical Reduction of Aryl Diazonium Cations
111(1)
5.3 Chemical Modification of Nano-objects by Reduction of Diazonium Salts
112(7)
5.3.1 Surface Modification of Carbon Nano-objects via Chemical Reduction of Aryl Diazonium Cations
112(4)
5.3.2 Surface Modification of Metal and Metal Oxide Nano-objects via Chemical Reduction of Aryl Diazonium Cations
116(3)
5.4 Summary and Conclusions
119(6)
Acknowledgments
120(1)
References
120(5)
6 Polymer Grafting to Aryl Diazonium-Modified Materials: Methods and Applications
125(34)
Sarra Gam-Derouich
Samia Mahouche-Chergui
Hatem Ben Romdhane
Mohamed M. Chehimi
6.1 Introduction
125(2)
6.2 Methods for Grafting Coupling Agents from Aryl Diazonium Compounds
127(3)
6.3 Grafting Macromolecules to Surfaces through Aryl Layers
130(21)
6.3.1 Binding Macromolecules to Surfaces by a Grafting from Strategy
130(1)
6.3.1.1 Surface-Initiated Atom Transfer Radical Polymerization (SI-ATRP)
130(12)
6.3.1.2 Surface-Initiated Reversible Addition-Fragmentation Chain Transfer (SI-RAFT)
142(1)
6.3.1.3 Surface-Initiated Photopolymerization
143(3)
6.3.1.4 Alternative Methods
146(1)
6.3.2 Attachment of Macromolecules through Grafting onto Strategies
147(1)
6.3.2.1 Photochemical Attachment
147(1)
6.3.2.2 Ring Opening
148(1)
6.3.2.3 Acylation
149(1)
6.3.2.4 Click Chemistry
149(1)
6.3.2.5 Diazotation of Substrates and Macromolecules
150(1)
6.4 Adhesion of Polymers to Surfaces through Aryl Layers
151(2)
6.5 Conclusion
153(6)
References
153(6)
7 Crafting Polymer Films onto Material Surfaces: The One-Step Redox Processes
159(22)
Guy Deniau
Serge Palacin
Alice Mesnage
Lorraine Tessier
7.1 Cathodic Electrografting (CE) in an Organic Medium
160(4)
7.1.1 Direct Cathodic Electrografting of Vinylic Polymers
160(2)
7.1.2 Indirect Cathodic Electrografting
162(2)
7.2 Surface Electroinitiated Emulsion Polymerization (SEEP)
164(7)
7.2.1 Characterization of Poly(Butyl Methacrylate) Films
166(1)
7.2.2 Determination of the Film Structure
167(2)
7.2.3 Reduction of Protons and the Role of Hydrogen Radicals
169(1)
7.2.4 Mechanism of SEEP
170(1)
7.3 Chemical Grafting via Chemical Redox Activation (Graftfast™)
171(6)
7.3.1 Process without Vinylic Monomer
172(2)
7.3.2 Process with Vinylic Monomer
174(1)
7.3.2.1 Type of Materials
174(1)
7.3.2.2 Parameters Controlled in the Process
174(3)
7.4 Summary and Conclusions
177(4)
References
178(3)
8 Electrografting of Conductive Oligomers and Polymers
181(16)
Jean Christophe Lacroix
Jalal Ghilane
Luis Santos
Gaelle Trippe-Allard
Pascal Martin
Hyacinthe Randriamahazaka
8.1 Introduction
181(1)
8.2 Conjugated Oligomers and Polymers
181(3)
8.3 Surface Grafting Based on islectroreduction of Diazonium Salts
184(3)
8.4 Polyphenylene and Oligophenylene-Tethered Surface Prepared by the Diazonium Reduction of Aniline or 4-Substituted Aniline
187(1)
8.5 n-Doping and Conductance Switching of Grafted Biphenyl, Terphenyl, Nitro-biphenyl and 4-Nitroazobenzene Mono- and Multilayers
187(3)
8.6 p-Doping and Conductance Switching of Grafted Oligo-Phenylthiophene or Oligothiophene Mono- and Multilayers
190(2)
8.7 p-Doping and Conductance Switching of Grafted Oligoaniline Mono- and Multilayers
192(1)
8.8 Conclusion and Outlook
193(4)
References
195(2)
9 The Use of Aryl Diazonium Salts in the Fabrication of Biosensors and Chemical Sensors
197(22)
J. Justin Gooding
Guozhen Liu
Alicia L. Gui
9.1 Introduction
197(3)
9.1.1 Sensors and Interfacial Design
197(1)
9.1.2 Molecular Level Control over the Fabrication of Sensing Interfaces
198(2)
9.2 The Important Features of Aryl Diazonium Salts with Regard to Sensing
200(1)
9.3 Sensors and Biosensors Fabricated Using Aryl Diazonium Salts
201(22)
9.3.1 Chemical Sensors -- Sensors Fabricated via the Immobilization of Chemical Recognition Species
201(4)
9.3.2 Biosensors
205(1)
9.3.2.1 Enzyme Biosensors
206(2)
9.3.2.2 Immunobiosensors
208(2)
9.3.2.3 DNA-Based Biosensors
210(13)
9.3.2.4 Cell-Based Biosensors
223(1)
9.4 Conclusions
223
References
224
10 Diazonium Compounds in Molecular Electronics
219(22)
Richard McCreery
Adam Johan Bergren
10.1 Introduction
219(3)
10.2 Fabrication of Molecular Junctions Using Diazonium Reagents
222(4)
10.2.1 Substrates for Diazonium-Derived Molecular Junctions
222(1)
10.2.2 Surface Modification Using Diazonium Chemistry
223(2)
10.2.3 Application of Top Contacts
225(1)
10.3 Electronic Performance of Diazonium-Derived Molecular Junctions
226(9)
10.3.1 Surface Diffusion Mediated Deposition (SDMD)
227(3)
10.3.2 Structural Control of Molecular Junction Behavior
230(2)
10.3.3 Redox Reactions in Molecular Junctions
232(1)
10.3.4 Microfabricated Molecular Devices Made with Diazonium Chemistry
233(2)
10.4 Summary and Outlook
235(6)
Acknowledgments
236(1)
References
236(5)
11 Electronic Properties of Si Surfaces Modified by Aryl Diazonium Compounds
241(14)
Jorg Rappich
Xin Zhang
Karsten Hinrichs
11.1 Introduction
241(1)
11.2 Experimental Techniques to Characterize Electronic Properties of Si Surfaces in Solutions
242(9)
11.2.1 In Situ Photolurninescence and Photo Voltage Measurements
242(2)
11.2.2 In Situ PL and PV Measurements during Electrochemical Grafting
244(1)
11.2.3 Reaction Scheme of the Electrochemical Grafting via Diazonium Ions
245(1)
11.2.4 Change in IPL and UPV during Electrochemical Grafting onto Si Surfaces
246(2)
11.2.5 Change in Band Bending and Work Function after Electrochemical Grafting onto Si Surfaces
248(1)
11.2.6 pH Dependence and Enhanced Surface Passivation
249(2)
11.3 Conclusion and Outlook
251(4)
Acknowledgments
252(1)
References
252(3)
12 Non-Diazonium Organic and Organometallic Coupling Agents for Surface Modification
255(28)
Fetah I. Podvorica
12.1 Amines
255(9)
12.1.1 Characterization of the Grafted Layer
257(1)
12.1.1.1 Electrochemical Methods
257(1)
12.1.1.2 Surface Analysis Techniques
258(1)
12.1.2 Chemical Grafting
259(1)
12.1.3 Localized Electrografting
260(1)
12.1.4 Grafting Mechanism
261(1)
12.1.5 Applications
262(2)
12.2 Arylhydrazines
264(2)
12.3 Aryltriazenes
266(1)
12.4 Alcohols
267(1)
12.4.1 Observation and Characterization of the Film
268(1)
12.4.2 Applications
269(1)
12.5 Grignard Reagents
270(2)
12.5.1 Characterization of the Layers
271(1)
12.5.2 Grafting Mechanism
272(1)
12.6 Onium Salts
272(2)
12.6.1 Iodonium Salts
272(1)
12.6.2 Sulfonium Salts
273(1)
12.6.3 Ammonium Salts
273(1)
12.7 Alkyl Halides
274(1)
12.8 Conclusion
275(8)
References
276(7)
13 Various Electrochemical Strategies for Grafting Electronic Functional Molecules to Silicon
283(26)
Dinesh K. Aswal
Shankar Prasad Koiry
Shiv Kumar Gupta
13.1 Introduction
283(1)
13.2 Architecture of Hybrid Devices
284(3)
13.2.1 Molecular Dielectrics and Wires
285(1)
13.2.2 Molecular Diodes
286(1)
13.2.3 Resonant Tunnel Diodes
286(1)
13.2.4 Molecular Transistors
286(1)
13.3 Electrografting of Monolayers to Si
287(1)
13.3.1 Essential Requirements
287(1)
13.3.2 Experimental Process of Electrografting
287(1)
13.4 Negative Differential Resistance Effect in a Monolayer Electrografted Using a Diazonium Complex
288(5)
13.4.1 Electrografting of DHTT
288(2)
13.4.2 NDR Effect in DHTT Monolayers
290(3)
13.5 Dielectric Monolayers Electrografted Using Silanes
293(2)
13.5.1 Mechanism of Electrografting
293(1)
13.5.2 Electrical Characterization
294(1)
13.6 Molecular Diodes Based on C60/Porphyrin-Derivative Bilayers
295(6)
13.6.1 Fabrication Process
296(1)
13.6.1.1 Electrografting of Acceptor C60 Layer on Si
296(1)
13.6.1.2 Self-Assembly of Donor Porphyrin Derivative Layer on C60/Si
297(1)
13.6.2 Rectification Characteristics of D--A Bilayers
298(3)
13.7 Memory Effect in TPP-C11 Monolayers Electrografted Using a C=C Linker
301(4)
13.7.1 Electrografting of TPP-C11 Monolayer
301(2)
13.7.2 Electrical Bistability and Memory Effect
303(2)
13.8 Summary
305(4)
References
305(4)
14 Patents and Industrial Applications of Aryl Diazonium Salts and Other Coupling Agents
309(14)
James A. Belmont
Christophe Bureau
Mohamed M. Chehimi
Sana Gam-Derouich
Jean Pinson
14.1 Introduction
309(1)
14.2 Patents
309(4)
14.2.1 The Surface Chemistry of Diazonium Salts
309(1)
14.2.2 The Surface Chemistry of Other Coupling Agents
310(1)
14.2.3 Post-Modification of the Grafted Layers
310(1)
14.2.4 Composite Materials
310(2)
14.2.5 The Surface Modification of Nano-objects
312(1)
14.2.6 Microelectronics
312(1)
14.2.7 Biomedical Applications
312(1)
14.2.8 Sensors, Biosensors, Surfaces for Biological Applications
312(1)
14.2.9 Energy Conversion
313(1)
14.3 Industrial Applications
313(6)
14.3.1 The Development of Modified Carbon Blacks
333
14.3.2 Industrial Applications of the Electropolymerization of Vinylics: Alchimer and AlchiMedics
314(1)
14.3.2.1 From Research to Development
314(1)
14.3.2.2 Application of eG™ to Drug-Eluting Stents: AlchiMedics
315(2)
14.3.2.3 Application of eG™ to Copper Interconnects: Alchimer
317(2)
14.4 Conclusion
319(4)
References
319(4)
Index 323
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.
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