Chemistry of Nanocarbons / Edition 1

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Overview

During the last decade, fullerenes and carbon nanotubes have attracted special interest as new nanocarbons with novel properties. Because of their hollow caged structure, they can be used as containers for atoms and molecules, and nanotubes can be used as miniature test-tubes. Chemistry of Nanocarbons presents the most up-to-date research on chemical aspects of nanometer-sized forms of carbon, with emphasis on fullerenes, nanotubes and nanohorns. All modern chemical aspects are mentioned, including noncovalent interactions, supramolecular assembly, dendrimers, nanocomposites, chirality, nanodevices, host-guest interactions, endohedral fullerenes, magnetic resonance imaging, nanodiamond particles and graphene. The book covers experimental and theoretical aspects of nanocarbons, as well as their uses and potential applications, ranging from molecular electronics to biology and medicine.

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Editorial Reviews

From the Publisher
"This volume presents the most up-to-date research on the chemical aspects (both experimental and theoretical) of nanometer-sized forms of carbon, paying special attention to fullerenes, nanotubes, and nanohorns. Contributors discuss topics such as noncovalent interactions, supramolecular assembly, dendrimers, nanocomposites, chirality, nanodevices, host-guest interactions, endohedral fullerenes, magnetic resonance imaging, nanodiamond particles, and graphene." (Booknews, 1 April 2011)

"All three editors are prolific authors in their own right, and their high standing among scientists in the nanocarbon community has enabled them to recruit an exceptionally distinguished team of authors for the chapters. The book is quite reasonably priced and belongs in the personal libraries of all scientists who are actively engaged in research on the chemistry of nanocarbons. Every university chemistry library should also have a copy." (JACS, February 2011)"The book does provide a useful reference resource for the topics covered and is a likely addition to the international bookshelf." (Chemistry World, December 2010)

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Product Details

  • ISBN-13: 9780470721957
  • Publisher: Wiley
  • Publication date: 8/16/2010
  • Edition number: 1
  • Pages: 526
  • Product dimensions: 6.80 (w) x 9.90 (h) x 1.30 (d)

Meet the Author

Fred Wudl is a Professor of Chemistry and Materials and Co-Director of the Center for Polymers and Organic Solids at the University of California, Santa Barbara. He is most widely known for his work on organic conductors and superconductors. Currently he is interested in the optical and electrooptical properties of processable conjugated polymers as well as in the organic chemistry of fullerenes.

Shigeru Nagase is Professor at the Institute for Molecular Science, Okazaki, Japan. He has made a wide range of original contributions in theoretical and computational chemistry. He has performed many important studies of fullerene, endofullerenes, carbon nanotubes and carbon peapods as well as silicon and germanium clusters.

Takeshi Akasaka is Professor at the Center for Tsukuba Advanced Research Alliance TARA Center) and Department of Chemistry, University of Tsukuba, Japan. His research interests cover the development and chemical functionalization of fullerenes, metallofullerenes, endofullerenes and carbon nanotubes.

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Table of Contents

Preface

Acknowledgements

Contributors

Abbreviations

1 Noncovalent Functionalization of Carbon Nanotubes Andreas Hirsch Hirsch, Andreas 1

1.1 Introduction 1

1.2 Overview of Functionalization Methods 2

1.3 The Noncovalent Approach 3

1.3.1 Dispersability of Carbon Nanotubes 3

1.3.2 The Role of Noncovalent Functionalization in Nanotube Separation 26

1.4 Conclusion 35

References 35

2 Supramolecular Assembly of Fullerenes and Carbon Nanotubes Hybrids Nazario Martin Martin, Nazario 49

2.1 Introduction 49

2.2 Hydrogen Bonded C60 Donor Ensembles 50

2.3 Concave exTTF Derivatives as Recognizing Motifs for Fullerene 56

2.4 Noncovalent Functionalization of Carbon Nanotubes 61

2.5 Summary and Outlook 67

Acknowledgements 68

References 68

3 Properties of Fullerene-Containing Dendrimers Jean-Francois Nierengarten Nierengarten, Jean-Francois 73

3.1 Introduction 73

3.2 Dendrimers with a Fullerene Core 74

3.2.1 A Fullerene Core to Probe Dendritic Shielding Effects 74

3.2.2 Light Harvesting Dendrimers with a Fullerene Core 77

3.3 Fullerene-Rich Dendrimers 79

3.4 Conclusions 89

Acknowledgements 89

References 89

4 Novel Electron Donor Acceptor Nanocomposites Shunichi Fukuzumi Fukuzumi, Shunichi 93

4.1 Introduction 93

4.2 Electron Donor-Fullerene Composites 94

4.2.1 General 94

4.2.2 Donor-Fullerene Dyads for Photoinduced Electron Transfer 94

4.2.3 Donor-Fullerene Linked Multicomponent Systems 96

4.2.4 Supramolecular Donor-Fullerene Systems 96

4.2.5 Photoelectrochemical Devices and Solar Cells 99

4.3 Carbon Nanotubes 106

4.3.1 General 106

4.3.2 Carbon Nanotube - Electron Donor Acceptor Conjugates 108

4.3.3 Carbon Nanotube - Electron Donor Acceptor Hybrids 113

4.4 Other Nanocarbon Composites 116

References 117

5 Higher Fullerenes: Chirality and Covalent Adducts Carlo Thilgen Thilgen, Carlo 129

5.1 Introduction 129

5.1.1 Fullerene Chirality - Classification and the Stereodescriptor System 130

5.1.2 Reactivity and Regioselectivity 131

5.2 The Chemistry of C70 132

5.2.1 C70-Derivatives with an Inherently Chiral Functionalization Pattern 132

5.2.2 C70-Derivatives with a Non-Inherently Chiral Functionalization Pattern 148

5.2.3 Fullerene Derivatives with Stereogenic Centers in the Addends 152

5.3 The Higher Fullerenes Beyond C70 152

5.3.1 Isolated and Structurally Assigned Higher Fullerenes 152

5.3.2 Inherently Chiral Fullerenes - Chiral Scaffolds 153

5.4 Concluding Remarks 162

Acknowledgement 163

References 163

6 Application of Fullerenes to Nanodevices Eiichi Nakamura Nakamura, Eiichi 173

6.1 Introduction 173

6.2 Synthesis of Transition Metal Fullerene Complexes 174

6.3 Organometallic Chemistry of Metal Fullerene Complexes 176

6.4 Synthesis of Multimetal Fullerene Complexes 177

6.5 Supramolecular Structures of Penta(organo)[60]fullerene Derivatives 179

6.6 Reduction of Penta(organo)[60]fullerenes to Generate Polyanions 179

6.7 Photoinduced Charge Separation 180

6.8 Photocurrent-Generating Organic and Organometallic Fullerene Derivatives 181

6.8.1 Attaching Legs to Fullerene Metal Complexes 181

6.8.2 Formation of Self-Assembled Monomolecular Films 182

6.8.3 Photoelectric Current Generation Function of Lunar Lander-Type Molecules 183

6.9 Conclusion 185

References 185

7 Supramolecular Chemistry of Fullerenes: Host Molecules for Fullerenes on the Basis of π-π Interaction Takeshi Kawase Kawase, Takeshi 189

7.1 Introduction 189

7.2 Fullerenes as an Electron Acceptor 190

7.3 Host Molecules Composed of Aromatic π-systems 192

7.3.1 Hydrocarbon Hosts 192

7.3.2 Hosts Composed of Electron Rich Aromatic π-Systems 194

7.3.3 Host Molecules Bearing Appendants 195

7.3.4 Host Molecules with Dimeric or Polymeric Structures 197

7.4 Complexes with Host Molecules Based on Porphyrin π Systems 199

7.4.1 Hosts with a Porphyrin π System 199

7.4.2 Hosts with Two Porphyrin π Systems 200

7.5 Complexes with Host Molecules Bearing a Cavity Consisting of Curved π System 203

7.5.1 Host with a Concave Structure 203

7.5.2 Complexes with Host Molecules Bearing a Cylindrical Cavity 204

7.6 The Nature of the Supramolecular Property of Fullerenes 208

References 208

8 Molecular Surgery toward Organic Sy0thesis of Endohedral Fullerenes Koichi Komatsu Komatsu, Koichi 215

8.1 Introduction 215

8.2 Molecular-Surgery Synthesis of Endohedral C60 Encapsulating Molecular Hydrogen 216

8.2.1 Cage Opening 216

8.2.2 Encapsulation of a H2 Molecule 219

8.2.3 Encapsulation of a He Atom 219

8.2.4 Closure of the Opening 220

8.3 Chemical Functionalization of H2@C60 222

8.4 Utilization of the Encapsulated H2 as an NMR Probe 224

8.5 Physical Properties of an Encapsulated H2 in C60 226

8.6 Molecular-Surgery Synthesis of Endohedral C70 Encapsulating Molecular Hydrogen 227

8.6.1 Synthesis of (H2)2@C70 and H2@C70 227

8.6.2 Diels-Alder Reaction of (H2)2@C70 and H2@C70 231

8.7 Outlook 233

References 233

9 New Endohedral Metallofullerenes: Trimetallic Nitride Endohedral Fullerenes Harry C. Dorn Dorn, Harry C. 239

9.1 Discovery, Preparation, and Purification 239

9.2 Structural Studies 240

9.2.1 Cycloaddition Reactions 246

9.2.2 Free Radical and Nucleophilic Addition Reactions 250

9.2.3 Electrochemistry Studies of TNT-EMFs 252

9.3 Summary and Conclusions 254

References 254

10 Recent Progress in Chemistry of Endohedral Metallofullerenes Shigeru Nagase Nagase, Shigeru 261

10.1 Introduction 261

10.2 Chemical Derivatization of Mono-Metallofullerenes 262

10.2.1 Carbene Reaction 263

10.2.2 Nucleophilic Reaction 263

10.3 Chemical Derivatization of Di-Metallofullerenes 265

10.3.1 Bis-silylation 266

10.3.2 Cycloaddition with Oxazolidinone 267

10.3.3 Carbene Reaction 267

10.4 Chemical Derivatization of Trimetallic Nitride Template Fullerene 269

10.5 Chemical Derivatization of Metallic Carbaide Fullerene 271

10.6 Missing Metallofullerene 271

10.7 Supramolecular Chemistry 274

10.7.1 Supramolecular System with Macrocycles 274

10.7.2 Supramolecular System with Organic Donor 276

10.8 Conclusion 277

References 278

11 Gadonanostructures as Magnetic Resonance Imaging Contrast Agents Lon J. Wilson Wilson, Lon J. 287

11.1 Magnetic Resonance Imaging (MRI) and the Role of Contrast Agents (CAs) 287

11.2 The Advantages of Gadonanostructures as MRI Contrast Agent Synthons 289

11.3 Gadofullerenes as MRI Contrast Agents 290

11.4 Understanding the Relaxation Mechanism of Gadofullerenes 291

11.5 Gadonanotuhes as MRI Contrast Agents 294

Acknowledgement 297

References 297

12 Chemistry of Soluble Carbon Nanotubes: Fundamentals and Applications Naotoshi Nakashima Nakashima, Naotoshi 301

12.1 Introduction 301

12.2 Characterizations of Dispersion States 303

12.3 CNT Solubilization by Small Molecules 303

12.3.1 Surfactants 303

12.3.2 Aromatic Compounds 305

12.4 Solubilization by Polymers 309

12.4.1 Vinyl Polymers 309

12.4.2 Conducting Polymers 313

12.4.3 Condensation Polymers 314

12.4.4 Block Copolymers 314

12.5 Nanotube/Polymer Hybrids and Composites 315

12.5.1 DNA/Nanotube Hybrids 315

12.5.2 Curable Monomers and Nanoimprinting 317

12.5.3 Nanotube/Polymer Gel-Near IR Responsive Materials 318

12.5.4 Conductive Nanotube Honeycomb Film 320

12.6 Summary 323

References 323

13 Functionalization of Carbon Nanotubes for Nanoelectronic and Photovoltaic Applications Maurizio Prato Prato, Maurizio 333

13.1 Introduction 333

13.2 Functionalization of Carbon Nanotubes 333

13.3 Properties and Applications 336

13.3.1 Electron Transfer Properties and Photovoltaic Applications 336

13.3.2 Functionalized Carbon Nanotubes for Electrical Measurements and Field Effect Transistors 346

13.3.3 Biosensors 351

13.4 Conclusion 356

References 356

14 Dispersion and Separation of Single-walled Carbon Nanotubes Shigeru Nagase Nagase, Shigeru 365

14.1 Introduction 365

14.2 Dispersion of SWNTs 366

14.2.1 Dispersion of SWNTs Using Amine 366

14.2.2 Dispersion of SWNTs Using C60 Derivatives 368

14.2.3 Dispersion of SWNTs in Organic Solvents 371

14.3 Purification and Separation of SWNTs Using Amine 373

14.3.1 Purification and Separation of SWNTs Prepared by CVD Methods 373

14.3.2 Purification and Separation of Metallic SWNTs Prepared by Arc-Discharged Method 375

14.3.3 Preparation of SWNTs and Metallic SWNTs Films 377

14.4 Conclusion 380

References 380

15 Molecular Encapsulations into Interior Spaces of Carbon Nanotubes and Nanohorns M. Yudasaka Yudasaka, M. 385

15.1 Introduction 385

15.2 SWCNT Nanopeapods 386

15.2.1 Synthesis Methods 386

15.2.2 Electronic Structures of C60 Nanopeapods 387

15.3 Material Incorporation and Release in/from SWNH 394

15.3.1 Structure of SWNH and SWNHox 394

15.3.2 Liquid Phase Incorporation at Room Temperature 395

15.3.3 Adsorption Sites of SWNHox 397

15.3.4 Release of Materials from inside SWNHox 398

15.3.5 Plug 401

15.4 Summary 401

References 401

16 Carbon Nanotube for Imaging of Single Molecules in Motion Eiichi Nakamura Nakamura, Eiichi 405

16.1 Introduction 405

16.2 Electron Microscopic Observation of Small Molecules 406

16.3 TEM Imaging of Alkyl Carborane Molecules 407

16.4 Alkyl Chain Passing through a Hole 408

16.5 3D Structural Information on Pyrene Amide Molecule 409

16.6 Complex Molecule 4 Fixed outside of Nanotube 410

16.7 Conclusion 411

Acknowledgements 411

References 412

17 Chemistry of Single-Nano Diamond Particles Eiji Osawa Osawa, Eiji 413

17.1 Introduction 413

17.2 Geometrical Structure 417

17.3 Electronic Structure 419

17.4 Properties 422

17.4.1 Tight Hydration 422

17.4.2 Gels 424

17.4.3 Number Effect 425

17.5 Applications 425

17.5.1 Lubrication Water 426

17.6 Recollection and Perspectives 428

Acknowledgements 430

References 430

18 Properties of ir-electrons in Graphene Nanoribbons and Nanographenes Zhongfang Chen Chen, Zhongfang 433

18.1 Introduction 433

18.2 Edge Effects in Graphene Nanoribbons and Nanographenes 435

18.3 Electronic and Magnetic Properties of Graphene Nanoribbons and Nanographenes 438

18.3.1 Graphene Nanoribbons 438

18.3.2 Nanographenes 444

18.4 Outlook 456

Acknowledgement 456

References 456

19 Carbon Nano Onions Amit J. Palkar Palkar, Amit J. 463

19.1 Introduction 464

19.2 Physical Properties of Carbon Nano Onions Obtained from Annealing 465

19.2.1 Annealing Process 465

19.3 Raman Spectroscopy of Carbon Nano Onions Prepared by Annealing Nanodiamonds 466

19.3.1 X-Ray Diffraction Studies 467

19.3.2 Electrical Resistivity Studies 468

19.4 Electron Paramagnetic Resonance Spectroscopy 469

19.5 Carbon Nano Onions Prepared from Arcing Graphite Underwater 470

19.5.1 Mechanism of Formation 471

19.5.2 Properties of Carbon Nano Onions Obtained from Arc Discharge 471

19.6 Reactivity of Carbon Nano Onions (CNOs) 473

19.6.1 1, 3-Dipolar Cycloaddition Reaction 473

19.6.2 Amidation Reactions 474

19.6.3 [2+1] Cycloaddition Reactions 475

19.6.4 Free-Radical Addition Reactions 476

19.7 Potential Applications of CNOs 478

Acknowledgements 481

References 481

Index 485

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