Supramolecular chemistry of fullerenes and carbonnanotubes

Collating our current knowledge and the latest developments for enabling breakthrough discoveries, this book focuses on the synthesis and applications of materials that are based on supramolecular assemblies of carbon nanostructures,with an emphasis on fullerenes and nanotubes. In so doing, it provides readers with an overview of the different types of supramolecular architectures, accentuating the outstanding geometrical, electronic and photophysical propertiesof the building blocks and the resulting structures. It makes use of basic concepts and real-life applications -- from simple syntheses to complex architectures, from instructive examples to working experimental procedures, and from photophysics to solar cells. A large part of each chapter is devoted to the methods and possibilities of controlling and tuning these molecular assemblies in order to obtain working devices.Fascinating reading for materials scientists, organic chemists, molecular physicists, and those in the semiconductor industry. INDICE: Preface XIList of Contributors XIII1 Carbon Nanostructures: Covalent and Macromolecular Chemistry 1Francesco Giacalone, Ma Ángeles Herranz, and Nazario Martín1.1 Introduction 11.2 Fullerene-Containing Polymers 21.3 Carbon Nanotubes 101.3.1 Defect Functionalization 111.3.2 Sidewall Functionalization 131.4 Graphenes 161.4.1 Covalent Functionalization 171.4.2 Noncovalent Functionalization 171.5 Summary and Conclusions 20References 202 Hydrogen-Bonded Fullerene Assemblies 27José Santos, Beatriz M. Illescas, Luis Sánchez, and NazarioMartín2.1 Introduction 272.2 Hydrogen-Bonded Fullerene-Based Supramolecular Structures 282.3 Hydrogen-Bonded Fullerene-Based Donor-Acceptor Structures 322.4 Applications 46References 493 Receptors for Pristine Fullerenes Based on Concave-Convex p-p Interactions 55Takeshi Kawase3.1 Introduction 553.2 Fullerene Receptors Based on Traditional Hosts 563.2.1 Simple Traditional Hosts 563.2.2 Modified Traditional Host Molecules 593.2.3 Receptors Bearing a Dimeric Structure of Traditional Host Molecules 623.3 Hydrocarbon Receptors 643.4 Receptors Bearing a Curved Conjugated System 663.4.1 Receptors Based on Bowl-Shaped Conjugated Systems 663.4.2 Receptors Bearing a Cylindrical Cavity 673.4.3 Carbon Nanorings 683.5 Conclusions 72References 724 Cooperative Effects in the Self-Assembly of Fullerene Donor Ensembles 79Jean-François Nierengarten4.1 Introduction 794.2 Allosteric Cooperativity 804.2.1 General Principle 804.2.2 AllostericCooperativity in Supramolecular Fullerene Donor Ensembles 814.3 Chelate Cooperativity 884.3.1 General Principle 884.3.2 Binding of a Divalent Ligand AA to a Divalent Receptor BB 914.3.3 Binding of a Divalent Asymmetric Ligand AC to aComplementary Receptor BD 954.4 Conclusions 984.5 Experimental Details 994.5.1 General 1004.5.2 UV-Visible Titrations 1004.5.3 Luminescence Titrations 100References 1045 Fullerene-Containing Rotaxanes and Catenanes 107Aurelio Mateo-Alonso5.1 Introduction 1075.1.1 Synthetic Strategies 1075.1.1.1 Rotaxanes 1075.1.1.2 Catenanes 1085.1.2 Bistable Rotaxanes and Catenanes 1095.2 Fullerene Rotaxanes and Catenanes 1105.2.1 Metal Coordination 1105.2.2 p Stacking Interactions 1115.2.3 Hydrogen Bonds 1135.3 Conclusions 123References 1246 Biomimetic Motifs Toward the Construction of Artificial Reaction Centers 127Bruno Grimm and Dirk M. Guldi6.1 Introduction 1276.2 Supramolecular Architectures for Solar Energy Conversion 1306.2.1 General Considerations 1306.2.2 Coulomb Interactions 1346.2.3 p-p Stacking 1376.2.4 Hydrogen Bonding 1436.2.5 Metal-Ligand Coordination 1506.3 Outlook 154References 1547 Supramolecular Chemistry of Fullerene-Containing Micelles and Gels 159Hongguang Li, Sukumaran Santhosh Babu, and Takashi Nakanishi7.1 Introduction 1597.2 Solubilization of Pristine C60 in Surfactant Assemblies 1607.2.1 Solubilizaiton in Micelles 1607.2.2 Solubilization in Vesicles 1627.3 Self-Assemblies of Amphiphilic C60 Derivatives 1647.4 Gels of Fullerenes 1667.5 Conclusions and Outlook 169References 1708 Fullerene-Containing Supramolecular Polymers and Dendrimers 173Takeharu Haino and Toshiaki Ikeda8.1 Introduction 1738.2 Fabrication of [60]Fullerene Polymeric Array 1748.3Supramolecular Polymerization of Functionalized [60]Fullerene 1788.3.1 Ionic Interaction 1798.3.2 Hydrogen Bonding Interaction 1828.3.3 Host-Guest Interaction 1858.4 Supramolecular [60]Fullerene Dendrimer 1888.4.1 Dendrimers with Peripheral Fullerene 1888.4.2 Dendrimers with Inner Fullerene 1938.5 Conclusions 198References 1989 [60]Fullerene-Containing Thermotropic Liquid Crystals 203Daniel Guillon, Bertrand Donnio, and Robert Deschenaux9.1 Introduction 2039.2 Noncovalent C60 Derivatives 2049.2.1 The Liquid-Crystalline Supramolecular Complex of C60 with a Cyclotriveratrylene Derivative 2049.2.2 Supramolecular Complex Composed of Rigid Dendritic Porphyrin and Fullerene 2069.2.3 Self-Assembled Columns of C60 2079.2.4 Phthalocyanine-[60]Fullerene Dyads in Liquid Crystals 2089.3 Covalent C60 Derivatives 2089.3.1 Liquid-Crystalline Methanofullerene- and Fulleropyrrolidine-Based Poly(Aryl Ester) Dendrons 2089.3.2 Liquid-Crystalline Fulleropyrrolidine-Based Poly(Benzyl Ether) Dendrons 2129.3.3 Liquid-Crystalline Fullero(Codendrimers) 2189.3.4 Polypedal [60]Fullerenes 2239.3.5 Conical-Like ‘‘Shuttlecock’’ [60]Fullerenes 2279.4 Conclusions 232References 23310 Supramolecular Chemistry of Fullerenes on Solid Surfaces 237Roberto Otero, José María Gallego, Nazario Martín, and Rodolfo Miranda10.1 Introduction 23710.2 Fullerenes on Nonpatterned Metal Surfaces 23810.2.1 Nature and Strength of Fullerene-Metal Interactions 23810.2.2 Translational and Orientational Order of Fullerene Layers on Flat Metal Surfaces 23910.2.3 Conventional Approaches to 2DFullerene Supramolecular Chemistry: Fullerene Functionalization 24010.3 Surface Templates for Fullerene Adsorption 24310.3.1 0D Point Defects and Single-Molecule Arrays 24310.3.2 1D Line Defects: Molecular Chains 24410.3.3 2D Nanomeshes 24610.4 Supramolecular Aggregation of Fullerenes and other Organic Specieson Surfaces 24810.4.1 Self-Assembled Monolayers as Hosts for Fullerenes on Solid Surfaces 24910.4.2 Coassembly of Fullerenes and Other Organic Species 25110.5 Outlook 258References 25911 Supramolecular Chemistry of Carbon Nanotubes 263Bruno Jousselme, Arianna Filoramo, and Stéphane Campidelli11.1 Introduction 26311.2 Supramolecular Carbon Nanotube Hybrids 26411.2.1 Carbon Nanotube and Surfactants 26411.2.1.1 Suspension of Single-Wall Carbon Nanotubes (Why, How, and What for?) 26411.2.2 p Stacking Interactions 27011.2.2.1 Pyrene Derivatives27011.2.2.2 Other Cyclic Aromatic Compounds 27611.2.2.3 Porphyrins and Derived Structures 27711.2.3 Polymers and Wrapping 28011.2.4 Filling Nanotubes 28311.3 Conclusions 288References 28812 Supramolecular Chemistry of Fullerenes and Carbon Nanotubes at Interfaces: Toward Applications 301Riccardo Marega, DavideGiust, Adrian Kremer, and Davide Bonifazi12.1 Introduction 30112.2 Fullerene Interfaces 30212.2.1 Fullerenes at the Liquid-Liquid and Micellar Interfaces 30312.2.2 Fullerenes at the Solid-Liquid Interface 30712.2.3 Fullerenes at the Gas-Solid Interface 31012.2.4 Fullerenes at the Biological Interface 31312.3 Carbon Nanotubes 31712.3.1 Carbon Nanotubes at the Liquid-Liquid Interface 31712.3.2 Carbon Nanotubes at the Solid-Liquid Interface 32012.3.3 Carbon Nanotubes at the Gas-Solid Interface 32512.3.4 Carbon Nanotubes at the Biological Interface 32712.4 Conclusions 334References 33513 Applications of Supramolecular Ensembles with Fullerenes and CNTs: Solar Cells and Transistors 349Hiroshi Imahori and Tomokazu Umeyama13.1 Introduction 34913.2 Solar Cells 35013.2.1 Fullerene-Based Solar Cells 35013.2.1.1 Self-Assembled Monolayers 35013.2.1.2 Layer-by-Layer Deposition 35313.2.1.3 Electrochemical Deposition 35413.2.1.4 Solution-Processed Bulk Heterojunction Solar Cells 35913.2.1.5 Hydrogen Bonding Systems 36013.2.1.6 Coordination Bonding Systems 36213.2.2 Carbon Nanotubes 36313.3Transistors 36613.3.1 Fullerenes 36613.3.2 Carbon Nanotubes 36613.4 Summary 368References 36914 Experimental Determination of Association Constants Involving Fullerenes 375Emilio M. Pérez Àlvarez and Nazario Martín14.1 Planning a Titration Experiment 37514.2 Performing a Titration 37614.3 Choosing the Spectroscopic Method 37814.4 Analyzing the Data 37914.5 Determining Stoichiometry 38014.6 Estimating Errors 38114.7 Fullerenes as Guests: Spectroscopic Properties 38114.8 Determination of the Binding Constant of an exTTF-based Host toward C60: A Practical Example 38514.9 Conclusions 389References 390Index 391

• ISBN: 978-3-527-32789-8
• Editorial: Wiley-VCH
• Encuadernacion: Cartoné
• Páginas: 418
• Fecha Publicación: 18/04/2012
• Nº Volúmenes: 1
• Idioma: Inglés