Contents. Preface XV List of Contributors XIX

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1 V Preface XV List of Contributors XIX 1 Carbon Nanotubes and Related Structures: Production and Formation 1 Mark H. Rümmeli, Paola Ayala, and Thomas Pichler 1.1 Introduction Carbon Nanotube Production Arc Discharge Laser Ablation Chemical Vapor Deposition Miscellaneous Synthesis Methods Catalysts Metallic Catalysts Ceramic Catalysts Catalyst Free Growth Enhancement Growth Mechanisms Floating Catalyst Methods Supported Catalyst Routes Catalyst-Free Routes Functionalization Purification Future Perspectives 17 References 17 2 Theory of Electronic and Optical Properties of DNA SWNT Hybrids 23 Slava V. Rotkin and Stacy E. Snyder 2.1 Introduction Physical Structure and Bonding in Nanotube DNA Hybrids: A Short Review Quantum Mechanical Modeling of the Hybrid Structure: Tight Binding Band Structure Calculations 26 Carbon Nanotubes and Related Structures. Edited by Dirk M. Guldi and Nazario Martín Copyright Ó 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN:

2 VI 2.4 Self-Consistent Computation Scheme: Acting Potential Screening Factor and the Dielectric Permittivity Polarization Component of Cohesion Energy of the SWNT ssdna Hybrid Optical Absorption of SWNT DNA Hybrids Summary 47 References 48 3 Electrochemistry 53 Matteo Iurlo, Massimo Marcaccio, and Francesco Paolucci 3.1 Introduction Electronic Properties of SWNTs Electrode Potentials Versus Work Functions Electrochemistry at SWNTs Versus Electrochemistry of SWNTs Carbon Nanotubes for Electrochemical Energy Storage Devices Carbon Nanotubes for Electrochemical Sensors and Biosensors Electrochemistry of Carbon Nanotubes Cyclic Voltammetric Investigations of Solutions of Individual SWNTs Vis NIR Spectroelectrochemical Investigation of True Solutions of Unfunctionalized SWNTs Standard Redox Potentials of Individual SWNTs in Solution Fermi Level and Excitonic Binding Energy of the Nanotubes Conclusions and Perspectives 72 References 72 4 Photophysics 77 Tobias Hertel 4.1 Introduction Molecular Nanoparticles: Carbon Nanotubes Have it All Understanding Optical Properties A Tight Binding Description The Coulomb Interaction and Bound States Colloidal Chemistry Facilitates Detailed Study of Nanotube Optics Excited State Dynamics and Nonlinear Optics Outlook 98 References 98 5 Noncovalent Functionalization of Carbon Nanotubes 103 M a Ángeles Herranz and Nazario Martín 5.1 Introduction Early Insights in the Noncovalent Interaction of CNTs with Solvents and Classical Macrocyclic Scaffolds Noncovalent Interactions of CNTs with Small Aromatic Molecules 105

3 VII Anthracene Derivatives Pyrene Derivatives Other Polyaromatic Derivatives Noncovalent Interactions of CNTs with Heterocyclic Polyaromatic Systems Porphyrins, Phthalocyanines, and Sapphyrins Metallic Coordination Noncovalent Interactions of CNTs with Surfactants and Ionic Liquids Noncovalent Interactions of CNTs with Polymers Polymeric Amphiphiles Conjugated Polymers Biopolymers Optically Active SWCNTS Noncovalent Interactions of CNTs with Nanoparticles Summary and Conclusions 129 References Covalent Functionalization of Carbon Nanotubes 135 Frank Hauke and Andreas Hirsch 6.1 Introduction Chemical Functionalization of Carbon Nanotubes Derivatization Strategies Topology and Reactivity of Carbon Nanotubes Defect Group Functionalization of Carbon Nanotubes Defect Types and Defect Generation Functional CNT-Derivatives by Defect Functionalizing Sequences Soluble CNT-Derivatives Cofunctionalization of CNTs Asymmetric End-Functionalization of Carbon Nanotubes Nanoparticle and Quantum Dot: CNT Conjugates Surface Attachment of CNTs Molecular Electronic Devices Based on Carbon Nanotubes Carbon Nanotubes as Integrated Unit in Donor/Acceptor Assemblies Functional CNT Composite Architectures Carbon Nanotubes as Polymer Reinforcement Additives Functional CNT Derivatives in the Biological Context Functional Group Interconversion Direct Sidewall Functionalization of Carbon Nanotubes Fluorination and Nucleophilic Substitution Reactions of Fluorinated Carbon Nanotubes Hydrogenation of Carbon Nanotubes Epoxidation of Carbon Nanotubes [2þ1]-Cycloaddition Reactions 157

4 VIII The Addition of Carbenes and Nitrenes Nucleophilic Cyclopropanation: The Bingle Reaction Silylation of Carbon Nanotubes ,3-Cycloaddition Reactions Cycloaddition of Zwitterionic Intermediates Azomethine Ylide Addition [4þ2]-Cycloaddition Reactions: Diels Alder Reaction Alkali Metal-Based Reduction of Carbon Nanotubes with Subsequent Sidewall Functionalization Naphthalenides as Electron Transfer Reagents Reductive Alkylation of CNTs Other Electron Transfer Mediators Sidewall Functionalization of Carbon Nanotubes Based on Radical Chemistry Carbon-Centered Free Radicals Sulfur-Centered Free Radicals Oxygen-Centered Free Radicals Amination of Carbon Nanotube Sidewalls Diazonium-Based Functionalization Sequences Sidewall Functionalization Through Electrophilic Addition Sidewall Functionalization Through Nucleophilic Addition Carbon-Based Nucleophiles Nitrogen-Based Nucleophiles Conclusions 179 References Carbon-Based Nanomaterial Applications in Biomedicine 199 Prabhpreet Singh, Tatiana Da Ros, Kostas Kostarelos, Maurizio Prato, and Alberto Bianco 7.1 Introduction Carbon Nanotubes Structures, Characteristics, and Derivatization of Carbon Nanotubes Biological Applications of CNTs Cell Penetration Drug Delivery Gene Delivery Other Anticancer Approaches Neuron Interactions with CNTs Antioxidant Properties of CNTs Imaging using Carbon Nanotubes Various Applications of Carbon Nanotubes Carbon Nanotube Toxicity Carbon Nanohorns Structure, Characteristics and Functionalization of SWCNHs 213

5 IX Biomedical Applications of Carbon Nanohorns Carbon Nanohorn as Potent Laser Therapeutic Agent Carbon Nanohorn for Drug Delivery Toxicity of Carbon Nanohorns Carbon Nanodiamonds Introduction Carbon Nanodiamond as Delivery Vehicle Carbon Nanodiamond as Biomarker for Cellular Imaging Biocompatibility and Toxicity Conclusions 224 References Ground and Excited State Charge Transfer and its Implications 233 Vito Sgobba and Dirk M. Guldi 8.1 Introduction Ground and Excited State Features Ground State Charge Transfer CNT as Electron Acceptors Chemical Reduction Electrochemical Reduction Reduction by Doping Miscellaneous Ground State Charge Transfer CNT as Electron Donors Chemical Oxidation Electrochemical Oxidation Oxidation by Doping Excited State Charge Transfer CNT as Excited State Electron Acceptor Covalent Electron Donor Acceptor Conjugates Noncovalent Electron Donor Acceptor Hybrids Excited State Charge Transfer CNT as Ground State Electron Acceptor Covalent Electron Donor Acceptor Conjugates Noncovalent Electron Donor Acceptor Hybrids Excited State Charge Transfer CNT as Ground State Electron Donor Noncovalent Electron Donor Acceptor Hybrids Charge Transfer Interactions CNT and Polymers Implications of Ground State Charge Transfer Conducting Electrode Materials Counter Electrodes for DSSC Implications of Excited State Charge Transfer Active Component in Photoactive Layer Gas Sensors 273 References 274

6 X 9 Photovoltaic Devices Based on Carbon Nanotubes and Related Structures 291 Emmanuel Kymakis 9.1 Introduction Photovoltaic Cells Based on Carbon Nanotubes Carbon Nanotubes as Electron Acceptors in Organic PVs Hole Collecting Electrodes Related Structures Future Directions 300 References Layer-by-Layer Assembly of Multifunctional Carbon Nanotube Thin Films 305 Bong Sup Shim and Nicholas A. Kotov 10.1 Introduction Structure and Properties of CNTs Structural Organization in Multilayers of Carbon Nanotubes Electrical Conductor Applications Sensor Applications Fuel Cell Applications Nano-/Microshell LBL Coatings and Biomedical Applications Conclusions 315 References Carbon Nanotubes for Catalytic Applications 321 Eva Castillejos and Philippe Serp 11.1 Introduction Macroscopic shaping of CNTs Specific Metal Support Interaction Dispersion of the Active Phase Surface Area and Porosity of CNT CNT Surface Activation to Improve Particle Dispersion Specific Interactions of Metal Precursors with Surface Defects of CNTs and CNFs Influence of Catalyst Preparation Procedure on Metal Loading and Dispersion Electrically and Thermally Conductive Supports Electrical Conductive Supports Thermally Conductive Supports Mass Transfer Limitations Confinement Effect Conclusion 342 References 343

7 XI 12 Carbon Nanotubes as Containers 349 Thomas W. Chamberlain, Maria del Carmen Gimenez-Lopez, and Andrei N. Khlobystov 12.1 Introduction Mechanisms of Nanotube Filling Fullerenes as Guest Molecules Fullerene C Higher Fullerenes Endohedral Fullerenes Functionalized Fullerenes Other Types of Molecules Molecules Without Metal Atoms Organometallic and Coordination Compounds Ionic Compounds Salts Oxides and Hydroxides Other Inorganic Materials Nanoparticles in Nanotubes Concluding Remarks 380 References Carbon Nanohorn 385 Masako Yudasaka and Sumio Iijima Introduction Production Structure and Growth Mechanism Properties Functionalization Material Incorporation and Release Chemical Modification of Structure Defects Chemical Functionalization at Hole Edges Physical Modification Toxicity Drug Delivery Applications Summary 398 References Self-Organization of Nanographenes 405 Wojciech Pisula, Xinliang Feng, and Klaus Müllen 14.1 Introduction Graphene, Graphene Nanoribbon, and Nanographene Organization of Nanographenes Single Sheets of Nanographenes Organization in the Bulk State Liquid Crystalline Columnar Phases 412

8 XII Helical Packing of Discotic Nanographenes Complementary Interactions Charge Carrier Transport Along Nanographene Stacks Solution Aggregation and Fiber Formation Solution Alignment on Surfaces Thermal Processing Nanographenes in Heterojunctions for Solar Cells Processing of Nondiscotic Nanographenes Conclusions 444 References Endohedrals 455 Lai Feng, Takeshi Akasaka, and Shigeru Nagase 15.1 Introduction Recent Investigations in the Synthesis of Endohedral Metallofullerenes The Reactive Gas Atmosphere The Solid Additive Advances in Nonchromatographic Techniques for Separation of Endohedral Metallofullerenes Separation by Electrochemical Method Separation by Other Chemical Methods Structures of Endohedral Metallofullerenes Determined by X-Ray Crystallographic Method Monometallofullerenes Dimetallofullerenes Metallic Carbide Fullerenes and Metallic Oxide Fullerenes Trimetallic Nitride Fullerenes Electrochemical Properties of Endohedral Metallofullerenes Chemical Reactivities of Endohedral Metallofullerenes Reductions and Oxidations Cycloadditions Diels Alder Reaction Prato Reactions Carbene Reactions Bis-Silylation Cycloaddition via a Zwitterion Approach Nucleophilic Addition Radical Reactions Applications of Endohedral Metallofullerenes Magnetic Resonance Imaging (MRI) Contrast Agents Peapod and Nanorod Electron Donor/Acceptor Conjugate Concluding Remarks 480 References 481

9 XIII 16 Carbon Nanostructures: Calculations of Their Energetics, Thermodynamics, and Stability 491 Zdenek Slanina, Filip Uhlík, Shyi-Long Lee, Takeshi Akasaka, and Shigeru Nagase 16.1 Introduction Energetics and Thermodynamics of Clusters Stabilities of Empty Fullerenes Stabilities of Metallofullerenes Stabilities of Nonmetal Endohedrals Kinetic Control 507 References 511 Index 525

Ali Ahmadpour. Fullerenes. Ali Ahmadpour. Department of Chemical Engineering Faculty of Engineering Ferdowsi University of Mashhad

Ali Ahmadpour. Fullerenes. Ali Ahmadpour. Department of Chemical Engineering Faculty of Engineering Ferdowsi University of Mashhad Ali Ahmadpour Fullerenes Ali Ahmadpour Department of Chemical Engineering Faculty of Engineering Ferdowsi University of Mashhad 2014 World of Carbon Materials 2 Fullerenes 1985 Robert F. Curl Jr. Richard