Fullerenes and Related Structures

254 Pages·1999·9.613 MB·English

by  Andreas Hirsch (auth.), Prof. Dr. Andreas Hirsch (eds.)

199
Topics in Current Chemistry
Editorial Board:
A. de Meijere • K.N. Houk. H. Kessler
J.-M. Lehn. S.V. Ley. S.L. Schreiber • J. Thiem
B.M. Trost • F. V6gtle • H. Yamamoto
Springer
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Fullerenes and Related
Structures
Volume Editor: A. Hirsch
With contributions by
C. Bellavia-Lund, E Diederich, A. Hirsch, W. K. Hsu,
].C. Hummelen, H.W. Kroto, M. Prato, Y. Rubin,
M. Terrones, C. Thilgen, D. R. M. Walton, E Wudl
~ Springer
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ISSN 0340-1022
ISBN 3-540-64939-5
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Volume Editors
Prof. Dr. Andreas Hirsch
Institut fiir Organische Chemie
Universit~it Erlangen-Nfirnberg
Henkestrat]e 42
D-91054 Erlangen, Germany
E-mail: [email protected]
Editorial Board
Prof. Dr. Armin de Meijere Prof. K.N. Houk
Institut fiir Organische Chemie Department of Chemistry and Biochemistry
der Georg-August -Universit/it University of California
Tammannstrage 2 405 Higard Avenue
D-37077 G6ttingen, Germany Los Angeles, CA 90024-1589, USA
E-maih ameijerl @uni-goettingen.de E-mail: [email protected]
Prof. Dr. Horst Kessler Prof. Jean-Marie Lehn
Institut ffir Organische Chemie Institut de Chimie
TU Mfinchen Universit6 de Strasbourg
Lichtenbergstrafle 4 1 rue Blaise Pascal, B.EZ 2961R8
D-85747 Garching, Germany F-67008 Strasbourg Cedex, France
E-maih [email protected]. E-mail: [email protected]
tu-muenchen.de
Prof. Steven V. Ley Prof. Stuart L. Schreiber
University Chemical Laboratory Chemical Laboratories
Lensfield Road Harvard University
Cambridge CB2 1EW, Great Britain 12 Oxford Street
E-maih svl l [email protected] Cambridge, MA 02138-2902, USA
E-mail: [email protected]
Prof. Dr. Joachim Thiem Prof. Barry M. Trost
Institut ftir Organische Chemie Department of Chemistry
Universitiit Hamburg Stanford University
Mar tin-Luther-King-Platz 6 Stanford, CA 94305-5080, USA
D-20146 Hamburg, Germany E-maih [email protected]
E-maih [email protected]
Prof. Dr. Fritz V6gtle Prof. Hisashi Yamamoto
Kekul~-Institut ftir Organische Chemie School of Engineering
und Biochemie der Universit/it Bonn Nagoya University
Gerhard-Domagk-St rage 1 Chikusa, Nagoya 464-01, Japan
D-53121 Bonn, Germany E-mail: [email protected]
E-maih [email protected]
Preface
The development of the chemistry of the fuUerenes was and continues
to be a most exciting challenge in chemical research of the 1990s. It is not
only the symmetrical structure and the beauty of these molecular allo-
tropes of carbon but also their unprecedented properties that keep a large
number of chemists, physisists and material scientists working with these
spherical architectures. It came as no surprise that, the discovery of the
fullerenes by Curl, Kroto and Smalley was rewarded with the Nobel prize
in 1996.
The prototype of all fullerenes is Buckminsterfullerene C60. Since it is the
most abundant fullerene obtained from macroscopic preparation procedures
such as the classical Krtitschmer-Huffman method, its chemical and physical
properties were developed in very quick sucession soon after it became available
in 1990. The icosahedral football shaped Buckminsterfullerene C60 is now the
most intensively studied molecule of all. Many principles of the chemistry of C60
are known. These allowone to tailor design new fullerene derivates with specific
properties useful for biological applications or as new materials. The main types
of fuUerene derivative are exohedral addition products, endohedral fullerenes,
heterofullerenes and cluster opened systems. Whereas many examples of the
first two groups are already known, sophisticated methods for the synthesis of
the latter two groups have started to emerge only recently.
It was also more recently that the chemistry of the less abundant and less
symmetrical higher fullerenes like C70 and C76 started to develop. Aspects
such as the inherent chirality of some of these carbon cages or the search for the
principles of the regioselectivities of addition reactions to their conjugated
n-system make these investigations most attractive.
The macromolecular analogues of the fullerenes are the carbon nanotubes.
The development of nanotube research started soon after the bulk production
of C60 and their identification in soot deposits formed during plasma arc ex-
periments. Next to their remarkable and at the same time variable shape the
carbon nanotubes have unique mechanical and electronic properties which are
very sensitive to their geometries and dimensions.
The present volume combines reports and the current status of the principles
of fullerene reactivity, of duster modified fullerenes, of higher fullerenes
and nanotubes and reviews potential applications of fullerene materials. This
volume is also meant to inspire interested fullerene researchers to find elegant
VIII Preface
solutions and improvements for the perpectives described here. Fullerene and
nanotube chemistry is still a young field and many facinating ideas await
realization.
Andreas Hirsch, Erlangen August 1998
Contents
Principles of Fullerene Reactivity
A. Hirsch ....................................
Ring Opening Reactions of Fullerenes:
Designed Approaches to Endohedral Metal Complexes
Y. Rubin .................................... 67
Heterofullerenes
J. C. Hummelen, C. Bellavia-Lund, E Wudl ................. 93
The Higher FuUerenes: Covalent Chemistry and Chirality
C. Thilgen, F. Diederich ............................ 135
Fullerene Materials
M. Prato .................................... 173
Nanotubes: A Revolution in Materials Science and Electronics
M. Terrones, W. K. Hsu, H.W. Kroto, D. R. M. Walton ............ 189
Author Index Volumes 151 - 199 ....................... 235
Contents of Volume 196
Carbon Rich Compounds I
Volume Editor: A. de Meijere
ISBN 3-540-64110-6
Design of Novel Aromatics Using the Loschmidt Replacement on Graphs
Y. Sritana-Anant, T. J. Seiders, J. S. Siegel
Modern Routes to Extended Aromatic Compounds
S. Hagen, H. Hopf
Carbon Rich Cyclophanes with Unusual Properties - an Update
B. K6nig
Unsaturated Oligoquinanes and Related Systems
R. Haag, A. de Meijere
The Centropolyindanes and Related Centro-Fused Polycyclic
Organic Compounds
D. Kuck
Contents of Volume 197
Dendrimers
Volume Editor: F.V6gtle
ISBN 3-540-64112-1
Iterative Synthesis in Organic Chemistry
N. Feuerbacher, F. V6gtle
Supramolecular Chemistry within Dendritic Structures
V. V. Narayanan, G.R. Newkome
Divergent Approaches to Phosphorus-Containing Dendrimers
and Their Functionalization
J.-P. Majoral, A.-M. Caminade
Chiral Dendrimers
13. Seebach, P. B. Rheiner, G. Greiveldinger, T. Butz, H. Sellner
Dendrimers with Polymeric Core: Towards Nanocylinders
A.-D. Schliiter
Electrochemical and Photochemical Properties
of Metal-Containing Dendrimers
M. Venturi, S. Serroni, A. Juris, S. Campagna, V. Balzani
Contents of Volume 198
Design of Organic Solids
Volume Editor: E. Weber
ISBN 3-540-64645-0
Directional Aspects of Intermolecular Interactions
J. P. Glusker
Supramolecular Synthons and Pattern Recognition
A. Nangia, G. R. Desiraju
Hydrogen-Bonded Ribbons, Tapes and Sheets as Motifs
for Crystal Engineering
R. E. Mel~ndez, A. D. Hamilton
Functional Organic Zeolite Analogues
Y. Aoyama
Crystalline Polymorphism of Organic Compounds
M. R. Caira