Chemistry of Nanocarbons E-Book

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 987

Veröffentlichungsjahr: 2010

Beschreibung

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.

Leseprobe

Contents

Cover

Title Page

Copyright

Preface

Acknowledgements

Contributors

Abbreviations

Chapter 1: Noncovalent Functionalization of Carbon Nanotubes

1.1 Introduction

1.2 Overview of Functionalization Methods

1.3 The Noncovalent Approach

1.4 Conclusion

References

Chapter 2: Supramolecular Assembly of Fullerenes and Carbon Nanotubes Hybrids

2.1 Introduction

2.2 Hydrogen Bonded C60 · Donor Ensembles

2.3 Concave exTTF Derivatives as Recognizing Motifs for Fullerene

2.4 Noncovalent Functionalization of Carbon Nanotubes

2.5 Summary and Outlook

Acknowledgements

References

Chapter 3: Properties of Fullerene-Containing Dendrimers

3.1 Introduction

3.2 Dendrimers with a Fullerene Core

3.3 Fullerene-Rich Dendrimers

3.4 Conclusions

Acknowledgements

References

Chapter 4: Novel Electron Donor Acceptor Nanocomposites

4.1 Introduction

4.2 Electron Donor-Fullerene Composites

4.3 Carbon Nanotubes

4.4 Other Nanocarbon Composites

References

Chapter 5: Higher Fullerenes: Chirality and Covalent Adducts

5.1 Introduction

5.2 The Chemistry of C70

5.3 The Higher Fullerenes Beyond C70

5.4 Concluding Remarks

Acknowledgement

References

Chapter 6: Application of Fullerenes to Nanodevices

6.1 Introduction

6.2 Synthesis of Transition Metal Fullerene Complexes

6.3 Organometallic Chemistry of Metal Fullerene Complexes

6.4 Synthesis of Multimetal Fullerene Complexes

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

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

6.7 Photoinduced Charge Separation

6.8 Photocurrent-Generating Organic and Organometallic Fullerene Derivatives

6.9 Conclusion

References

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

7.1 Introduction

7.2 Fullerenes as an Electron Acceptor

7.3 Host Molecules Composed of Aromatic π-systems

7.4 Complexes with Host Molecules Based on Porphyrin π Systems

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

7.6 The Nature of the Supramolecular Property of Fullerenes

References

Chapter 8: Molecular Surgery toward Organic Synthesis of Endohedral Fullerenes 215

8.1 Introduction

8.2 Molecular-Surgery Synthesis of Endohedral C60 Encapsulating Molecular Hydrogen

8.3 Chemical Functionalization of H2@C60

8.4 Utilization of the Encapsulated H2 as an NMR Probe

8.5 Physical Properties of an Encapsulated H2 in C60

8.6 Molecular-Surgery Synthesis of Endohedral C70 Encapsulating Molecular Hydrogen 2@C70 and H2@C70

8.7 Outlook 233

References

Chapter 9: New Endohedral Metallofullerenes: Trimetallic Nitride

9.1 Discovery, Preparation, and Purification

9.2 Structural Studies

9.3 Summary and Conclusions

References

Chapter 10: Recent Progress in Chemistry of Endohedral Metallofullerenes

10.1 Introduction

10.2 Chemical Derivatization of Mono-Metallofullerenes

10.3 Chemical Derivatization of Di-Metallofullerenes

10.4 Chemical Derivatization of Trimetallic Nitride Template Fullerene

10.5 Chemical Derivatization of Metallic Carbaide Fullerene

10.6 Missing Metallofullerene

10.7 Supramolecular Chemistry

10.8 Conclusion

References

Chapter 11: Gadonanostructures as Magnetic Resonance Imaging Contrast Agents

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

11.2 The Advantages of Gadonanostructures as MRI Contrast Agent Synthons

11.3 Gadofullerenes as MRI Contrast Agents

11.4 Understanding the Relaxation Mechanism of Gadofullerenes

11.5 Gadonanotubes as MRI Contrast Agents

Acknowledgement

References

Chapter 12: Chemistry of Soluble Carbon Nanotubes: Fundamentals and Applications 301 Tsuyohiko Fujigaya and Naotoshi Nakashima

12.1 Introduction

12.2 Characterizations of Dispersion States

12.3 CNT Solubilization by Small Molecules

12.4 Solubilization by Polymers

12.5 Nanotube/Polymer Hybrids and Composites

12.6 Summary

References

Chapter 13: Functionalization of Carbon Nanotubes for Nanoelectronic and Photovoltaic Applications

13.1 Introduction

13.2 Functionalization of Carbon Nanotubes

13.3 Properties and Applications

13.4 Conclusion

References

Chapter 14: Dispersion and Separation of Single-walled Carbon Nanotubes

14.1 Introduction

14.2 Dispersion of SWNTs 60 Derivatives

14.3 Purification and Separation of SWNTs Using Amine

14.4 Conclusion

References

Chapter 15: Molecular Encapsulations into Interior Spaces of Carbon Nanotubes and Nanohorns

15.1 Introduction

15.2 SWCNT Nanopeapods

15.3 Material Incorporation and Release in/from SWNH

15.4 Summary

References

Chapter 16: Carbon Nanotube for Imaging of Single Molecules in Motion

16.1 Introduction

16.2 Electron Microscopic Observation of Small Molecules

16.3 TEM Imaging of Alkyl Carborane Molecules

16.4 Alkyl Chain Passing through a Hole

16.5 3D Structural Information on Pyrene Amide Molecule

16.6 Complex Molecule 4 Fixed outside of Nanotube

16.7 Conclusion

Acknowledgements

References

Chapter 17: Chemistry of Single-Nano Diamond Particles

17.1 Introduction

17.2 Geometrical Structure

17.3 Electronic Structure

17.4 Properties

17.5 Applications

17.6 Recollection and Perspectives

Acknowledgements

References

Chapter 18: Properties of π-electrons in Graphene Nanoribbons and Nanographenes

18.1 Introduction

18.2 Edge Effects in Graphene Nanoribbons and Nanographenes

18.3 Electronic and Magnetic Properties of Graphene Nanoribbons and Nanographenes

18.4 Outlook

Acknowledgement

References

Chapter 19: Carbon Nano Onions

19.1 Introduction

19.2 Physical Properties of Carbon Nano Onions Obtained from Annealing

19.3 Raman Spectroscopy of Carbon Nano Onions Prepared by Annealing Nanodiamonds

19.4 Electron Paramagnetic Resonance Spectroscopy

19.5 Carbon Nano Onions Prepared from Arcing Graphite Underwater

19.6 Reactivity of Carbon Nano Onions (CNOs)

19.7 Potential Applications of CNOs 478

Acknowledgements

References

Colour Plates

Index

This edition first published 2010

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Library of Congress Cataloging-in-Publication Data

Akasaka, Takeshi.

Chemistry of nanocarbons / Takeshi Akasaka, Fred Wudl, Shigeru Nagase.

p. cm.

Includes bibliographical references and index.

ISBN 978-0-470-72195-7 (cloth)

1. Nanotubes. 2. Fullerenes. 3. Nanodiamonds. I. Wudl, Fred. II. Nagase,

Shigeru. III. Title.

TA418.9.N35A427 2010

620′.5–dc22

2010004437

A catalogue record for this book is available from the British Library.

ISBN 978-0-470-72195-7 (HB)

We dedicate this monograph to the memory of R. Smalley and to the original discoverers Harry Kroto and Sumio Iijima

Preface

The first time I heard about the possibility of the existence of the molecule we now call buckminsterfullerene was at a lecture given by the late Prof. Orville Chapman in the mid 1980s, followed by the first disclosure by Kroto et al. in their Nature paper of 1985. In 1990, while visiting Robert Haddon at the AT&T Bell laboratories, I learnt that it had actually been synthesized, not by chemists but by physicists, referring, of course, to a preprint by W. Kraetschmer et al's now famous 1990 Nature paper that was floating around the Labs. Since then, buckminsterfullerene has spawned an entire field of endeavor and this book tries to capture the most salient features of the novel molecular allotropes of carbon.

The chapters within this volume present the most up-to-date research on chemical aspects of nanometer sized forms of carbon. It therefore emphasizes the chemistry aspects of 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 reader will be exposed to the most recent potential and actual applications of these remarkable allotropes of carbon in molecular electronics as well as medicine. The authors of the nineteen chapters are the current principal exponents of nano allotropes of carbon.

The subjects of this book would not be possible without the pioneering work of (in alphabetical order) Curl, Huffman, Iijima, Kraetschmer, Kroto and Smalley, and it is hoped that the book's contents will contribute to the lasting memory of these scientists.

Acknowledgements

T. Akasaka, F. Wudl and S. Nagase gratefully acknowledge the support they received from their respective institutions during the process of this book's edition. We also thank the chapter authors for their prompt cooperation and help to produce this book that we believe will be an invaluable source of information to future researchers in the field.

Contributors

Akasaka, Takeshi, Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Japan

Ananta, Jeyarama S., Department of Chemistry & Smalley Institute of Nanoscale Science and Technology, Rice University, Houston, TX, USA

Backes, Claudia, Institute of Advanced Materials and Processes, University of Erlangen, Fuerth, Germany

Balch, Alan L., Department of Chemistry, University of California, Davis, CA, USA

Campidelli, Stéphane, CEA, IRAMIS, Laboratoire d'Electronique Moléculaire, Gif sur Yvette, France

Chaur, Manuel N., Department of Chemistry, Clemson University, Clemson, SC, USA

Chen, Zhongfang, Department of Chemistry, Institute for Functional Nanomaterials, University of Puerto Rico, PR, USA

Diederich, François, Laboratory of Organic Chemistry, ETH Zurich, Zurich, Switzerland

Dorn, Harry C., Department of Chemistry, Virginia Polytechnic Institute & State University, Blacksburg, VA, USA

Echegoyen, Luis, Department of Chemistry, Clemson University, Clemson, SC, USA

Fujigaya, Tsuyohiko, Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, Fukuoka, Japan

Fukuzumi, Shunichi, Department of Material and Life Science, Graduate School of Engineering, Osaka University, Japan

Gao, Xingfa, Department of Theoretical and Computational Molecular Science, Institute for Molecular Science, Myodaiji, Okazaki, Japan

Gibson, Harry W., Department of Chemistry, Virginia Polytechnic Institute & State University, Blacksburg, VA, USA

Guldi, Dirk M., Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), Erlangen, Germany

Herranz, Ma Ángeles, Departamento de Química Orgánica, Universidad Complutense, Madrid, Spain

Hirsch, Andreas, Institute of Organic Chemistry II, University of Erlangen, Erlangen, Germany

Iijima, S., Nanotube Research Center, Meijo University, Japan

Illescas, Beatriz M., Departamento de Química Orgánica, Universidad Complutense, Madrid, Spain

Imahori, Hiroshi, Institute for Integrated Cell-Material Sciences (iCeMS), Kyoto University, Kyoto, Japan

Jiang, De-en, Chemical Science Division, Oak Ridge National Laboratory, Oak Ridge, TN, USA

Kawase, Takeshi, Graduate School of Engineering, University of Hyogo, Hyogo, Japan

Komatsu, Koichi, Department of Environmental and Biotechnological Frontier Engineering, Fukui University of Technology, Fukui, Japan

Kraszewska, Agnieszka, Laboratory of Organic Chemistry, ETH Zurich, Zurich, Switzerland

Lu, Jing, Mesoscopic Physics Laboratory, Department of Physics, Peking University, Beijing, People's Republic of China

Maeda, Yutaka, Department of Chemistry, Tokyo Gakugei University, Koganei, Tokyo, Japan

Martin, Juan-José Cid, Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Strasbourg, France

Martín, Nazario, Departamento de Química Orgánica, Universidad Complutense, Madrid, Spain

Matsuo, Yutaka, Nakamura Functional Carbon Cluster Project, ERATO, Japan Science and Technology Agency and Department of Chemistry, The University of Tokyo, Tokyo, Japan

Murata, Michihisa, Institute for Chemical Research, Kyoto University, Kyoto, Japan

Murata, Yasujiro, Institute for Chemical Research, Kyoto University, Kyoto, Japan

Nagase, Shigeru, Institute for Molecular Science, Myodaiji, Okazaki, Japan

Nakamura, Eiichi, Nakamura Functional Carbon Cluster Project, ERATO, Japan Science and Technology Agency and Department of Chemistry, The University of Tokyo, Tokyo, Japan

Nakashima, Naotoshi, Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, Fukuoka, Japan

Nierengarten, Jean-François, Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Strasbourg, France

Okazaki, T., Nanotube Research Center, Meijo University, Japan

Olmstead, Marilyn M., Department of Chemistry, University of California, Davis, CA, USA

Ortiz, Angy, Department of Chemistry, Clemson University, Clemson, SC, USA

sawa, Eiji, Nanocarbon Research Institute, Ltd., Asama Research Extension Centre, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano, Japan

Palkar, Amit J., ConocoPhillips Company, Ponca City, Oklahoma, USA

Pérez, Emilio M., Departamento de Química Orgánica, Universidad Complutense, Madrid, Spain

Pinzon, Julio R., Department of Chemistry, Clemson University, Clemson, SC, USA

Prato, Maurizio, INSTM, Università di Trieste, Trieste, Italy

Thilgen, Carlo, Laboratory of Organic Chemistry, ETH Zurich, Zurich, Switzerland

Tsuchiya, Takahiro, Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Japan

Wilson, Lon J., Department of Chemistry & Smalley Institute of Nanoscale Science and Technology, Rice University, Houston, TX, USA

Yudasaka, M., Nanotube Research Center, Meijo University, Japan

Abbreviations

ACCVD  Aalcohol catalytic chemical vapor deposition

AFM  antiferromagnetic

AFM  atomic force microscopy

AGNRs  armchair-edged graphene nanoribbons

AMI  Austin model 1

AMOs  antibonding molecular orbitals

ArcNTs  AP-grade single-walled carbon nanotubes

ATRP  atom transfer radical polymerization

BET  Brunauer, Emmett, and Teller

BIGCHAP  N,N-bis(3-D-gluconamidopropyl) cholamide

BMOs  bonding molecular orbitals

BODA  bis-o-diynyl arene

BSA  bovine serum albumin

BWF  Breit–Wigner–Fano

CAs  circumacenes

CAN  ammonium cerium(IV) nitrate

CaNCN  calcium cyanamide

CAPTEAR  chemically adjusting plasma temperature, energy, and reactivity

CD  circular dichroism

CIP  Cahn, Ingold, Prelog

CNG  carbon nanographene

CNOs  carbon nano onions

CNs  carbon nanotubes

CNTs  carbon nanotubes

COOH  carboxylic acid

CPE  constant potential electrolysis

CPPAs  cyclic [n]paraphenyleneacetylenes

CSCNTs  cup-stacked carbon nanotubes

CSP  chiral stationary phases

CT  charge transfer

CV  cyclic voltammetry

CVD  chemical vapor deposition

DABCO  1,4-diazabicyclo[2.2.2]octane

DBU  1,8-diazabicyclo[5.4.0]undec-7-ene

DFT  density functional theory

DFT  discrete Fourier transform

DFT-GGA  density functional theory-generalized gradient-corrected approximation

DGU  density gradient ultracentrifugation

DLS  dynamic light scattering

DMA  dimethylacetamide

DMA  9,10-dimethylanthracene

DMAc  dimethylacetamide

DMAP  dimethylaminopyridine

DMF  dimethylformamide

DMRG  density matrix renormalization group

DMSO  dimethylsulfoxide

DN  detonation nanodiamond

DNA  deoxyribonucleic acid

DOS  density of states

DPV  differential pulse voltammetry

dsDNA  double-strand DNA

DTAB  dodecyltrimethylammonium bromide

DWNT  double wall carbon nanotube

ECF  extracellular fluid space

EMAPS  electromagnetically accelerated plasma spraying

EMFs  endohedral metallofullerenes

EPR  electron paramagnetic resonance

ES  electrostatic

exTTFs  π-extended tetrathiafulvalenes

FAD  flavine adenine dinucleotide cofactor

FET  field-effect transistors

FFF  field flow fractionation

FM  ferromagnetic

FTIR  Fourier transform infrared spectroscopy

GBL  γ-butyrolactone

G/D  graphite/defect

GGA  generalized-gradient approximation

GIAO  gauge-including atomic orbital

GlcNAc  N-acetyl-D-glucosamine

GNR  graphene nanoribbon

GOx  glucose oxidase

GPC  gel permeation chromatography

HEM  high energy mode

HiPco  high-pressure CO conversion

HMQC  hetero multiple bond correlation

HOMO  highest occupied molecular orbital

HOPG  highly oriented pyrolitic graphite

HPHT  high pressure high temperature

HPLC  high performance liquid chromatography

HRTEM  high-resolution transmission electron microscope

HSVM  high-speed vibration milling

HTAB  hexadecyltrimethylammonium bromide

IEC  ion exchange chromatography

IPCE  internal photon-to-current efficiency

IPR  isolated pentagon rule

IR  infrared

ITO  indium tin oxide

IUPAC  International Union of Pure and Applied Chemistry

LB  Langmuir-Blodgett

LCAO  linear combination of atomic orbitals

LDA  local density approximation

LDS  lithium, dodecyl sulfate

LPC  lysophosphatidylcholine

LPG  lysophosphatidylglycerol

LUMO  lowest unoccupied molecular orbital

MALDI-TOF-MS  matrix assisted laser desorption ionization time-of-flight mass spectrometry

MCPBA  m-chloroperbenzoic acid

MEM  maximum entropy method

MeOH  methanol

MNDO  modified neglect of differential overlap

MPWB1K  hybrid meta DFT method for kinetics

MRA  magnetic resonance angiography

MRI  magnetic resonance imaging

MWCNTs  multi-walled carbon nanotubes

MWNTs  multi-walled carbon nanotubes

NFE  nearly free electron

NHE  normal hydrogen electrode

NICS  nucleus independent chemical shifts

NIR  near-IR

NM  nonmagnetic

NMP  N-methyl-2-pyrrolidone

NMR  nuclear magnetic resonance

NMRD  nuclear magnetic relaxation dispersion

NSB  nonspecific binding

NW  nanowire

OC  o-carboxymethyl chitosan

ODA  octadecylamine

ODCB  o-dichlorobenzene

OITB  orbital interactions through bonds

OPV  oligophenylenevinylene

PABS  poly(m-aminobenzenesulfonic acid)

PAH  polycyclic aromatic hydrocarbons

PAMAM  poly(amido amine)

PAmPV  poly{(5-alkoxy-m-phenylenevinylene)-co-[(2,5-dioctyloxy-p-phenylene)-vinylene]}

PArcNTs  oxidized single-walled carbon nanotubes

PAs  periacenes

PBS  phosphate buffered saline

PCBM  methanofullerene phenyl-C61-butyric acid methyl ester

PDDA  poly(diallyl dimethylammonium) chloride

PEO  polyethylene oxide

PEO-PDEM  poly(ethylene oxide)-b-poly[2-(N,N-dimethylamino)ethyl methacrylate]

PEO-PDMS-PEO  poly(ethyleneoxide)-b-poly(dimethylsiloxane)-b-poly(ethylene oxide)

PEO-PPO  poly(ethylene oxide)-b-poly(propylene oxide)

PEO-PPO-PEO  poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide)

PDMS  poly(dimethylsiloxane)

PFG-NMR  pulsed-field gradient nuclear magnetic resonance

PFH-A  poly[(9,9-dihexylfluorenyl-2,7-diyl)-co-(9,19-anthracence)]

PFO  poly(9,9-dioctylfluorenyl-2,7-diyl

PFO-BT  poly[9,9-dioctylfluorenyl-2,7-diyl)-co-1,4-benzo-{2,1′-3}-thiadiazole)]

PhCN  benzonitrile

PL  photoluminescence

PLE  photoluminescence excitation

PLV  pulsed-laser vaporization

PMMA  poly(methylmethacrylate)

PMMA-PEO  poly(methylmethacrylate)-b-poly(ethylene oxide)

PmPV  poly-m-phenylenevinylene

PNIPAM  poly(N-isopropylacrylamide)

POAV  p-orbital axis vector analysis

PPEs  poly(aryleneethynylene)s

PPV  p-phenylenevinylene

PS-P4VP  polystyrene-b-poly(4-vinylpyridine)

PS-PBA  polystyrene-b-poly(tert-butyl acrylate)

PS-PBD-PS  polystyrene-b-polybutadiene-b-polystyrene

PS-PEO  polystyrene-b-poly(ethylene oxide)

PS-PI  polystyrene-b-polyisoprene

PS-PMAA  polystyrene-b-poly(methacrylic acid)

PS-PSCI  polystyrene-b-poly[sodium(2-sulfamate-3-carboxylate)isoprene]

PSA  prostate specific antigen

PSSn−  poly(sodium 4-styrenesulfonate)

PTCDA  perylene tetracarboxylic dianhydride

PVBTAn+  poly((vinylbenzyl)trimethylammonium chloride)

PVP  poly(4-vinylpyridine)

PZC  point of zero charge

QCM  quartz crystal microbalance

RBM  radial breathing mode

RDX  cyclotrimethylenetrinitramine

RNA  ribonucleic acid

SAM  self-assembled monolayers

SANS  small angle neutron scattering

SBM  Solomon-Bloembergen-Morgan

SC  sodium cholate

SCC-DFTB  self-consistent charges density functional theory of tight binding

SCCNT  stacked-cup carbon nanotubes

SDBS  sodium dodecyl benzene sulfonate

SDC  sodium deoxycholate

SDS  sodium dodecyl sulfate

SEC  size exclusion chromatography

SEM  scanning electron microscopy

SGC  sodium glycocholate

SiPc  silicon-phthalocyanine

SNBD  single-nano buckydiamond

SpA  staphylococcal protein A

ssDNA  single-strand DNA

STC  sodium taurocholate

STDC  sodium taurodeoxycholate

SWCNTs  single-walled carbon nanotubes

SWNHox  hole-opened single-walled nanohorns

SWNHs  single-walled nanohorns

SWNTs  single-walled carbon nanotubes

SWNs  single-walled carbon nanotubes

TDAE  tetrakis(dimethylamino)ethylene

TEM  transmission electron microscopic

TFA  trifluoroacetic acid

TGA  thermogravimetric analysis

THF  tetrahydrofuran

THPP  5,10,15,20-tetrakis(hexadecyloxyphenyl)-21H,23H-porphyrin

TMPD  N,N,N′,N′-tetramethyl-p-phenylenediamine

TMWCNTs  thin multi-walled carbon nanotubes

TNT  trinitrotoluene

TNTs  trimetallic nitride template endohedral fullerenes

TTAP  tetradecyl trimethyl ammonium bromide

TTF  tetrathiafulvalene

UDD  ultra-dispersed diamond

US  ultra-short

UV-vis  ultraviolet-visible

VDW  Van der Waals

VTMWCNTs  very thin multi-walled carbon nanotubes

VT-NMR  variable temperature nuclear magnetic resonance

XPS  X-ray photoelectron spectrum

XRD  X-ray diffraction

ZGNR  zigzag-edged graphene nanoribbon

ZINDO  Zerner  Intermediate Neglect of Differential Overlap

ZnNc  zinc naphthalocyanine

ZnP  zinc tetraphenylporphyrin

ZnPP  zinc protoporphyrin

1

Noncovalent Functionalization of Carbon Nanotubes

Claudia Backesa, b and Andreas Hirschb

aInstitute of Advanced Materials and Processes, Fuerth, Germany

bInstitute of Advanced Materials and Processes, Fuerth, Germany

1.1 Introduction

Within the past decades extensive research has shed light into the structure, reactivity and properties of carbon nanotubes (CNTs) [1–3]. This new carbon allotrope is theoretically constructed by rolling up a graphene sheet into a cylinder with the hexagonal rings joining seamlessly. Commonly, carbon nanotubes are classified into single-walled carbon nanotubes (SWCNTs) which consist of one cylinder and multi-walled carbon nanotubes (MWCNTs) comprising an array of tubes being concentrically nested. Depending on the roll-up vector which defines the arrangement of the hexagonal rings along the tubular surface, single-walled carbon nanotubes exhibit different physical and electronic properties, e.g. they either possess metallic or semiconducting character.

Apart from their outstanding electronic properties providing the foundation for multiple applications as nanowires, field-effect transistors and electronic devices [3–5], carbon nanotubes surmount any other substance class in their mechanical properties. The exceptionally high tensile modulus (640 GPa) and tensile strength (≈100 GPa) together with the high aspect ratio (300–1000) make nanotubes an ideal candidate for reinforcing fibers and polymers [6, 7].

However, in order to tap the full potential of nanotubes in electronics, photonics, as sensors or in composite materials, two major obstacles have to be overcome, e.g. separation according to diameter and/or chirality on the one hand and uniform dispersability in a solvent or matrix on the other hand. Responding to a growing interest, progress in the diameter control during carbon nanotube production has been achieved [8]. However, up to now, the as-produced material contains nanotubes of differing lengths, diameters and chiralities, therefore including semiconducting and metallic nanotubes. This inhomogeneity still forms the bottleneck for nanotube-based technological progress. Furthermore, the strong intertube van der Waals interactions of 0.5 eV/µm, which render nanotubes virtually insoluble in common organic solvents and water also constrict any application [9, 10].

Among the efforts to increase processability of this unique material, chemical and especially noncovalent functionalization represents a cornerstone, as in its nondestructive meaning it does not alter the intrinsic properties of CNTs. Furthermore, tailoring of the surface properties of carbon nanotubes is accessible, boosting solubility in a variety of solvents and increasing matrix interactions, as will be summarized within this chapter.