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The aesthetically pleasing molecular architectures of fullerenes and nanotubes are appealing not only because of their beauty but also because they are responsible for the many unprecedented chemical and physical properties of this compound class. Although succession of exciting new discoveries continues unabated fullerene research has become a mature science. It is now possible to predict fullerene chemistry, to design new structure variations like open fullerene clusters, heterofullerenes and endohedral fullerenes, and to develop fullerene materials and modified nanotubes with high potential for technological applications. This volume represents the state-of-the-art of fullerene research, focussing on areas showing high potential for future growth and practical applications. The authors are leading scientists whose groups are making major contributions in the field.



Principles of Fullerene Reactivity

The fullerenes have been established as new and versatile building blocks in organic chemistry. A large number of fascinating fullerene derivatives, especially of the icosahedral buck-minsterfullerene C60, have been synthesized. The chemistry of C60 continues to be good for many surprises. However, based on present knowledge a series of reactivity principles can be deduced which makes derivatization of this all carbon cluster more and more predictable. In this article first the geometric and electronic properties of the parent molecule are analyzed. The bent structure of the carbon network C60 and the filling of its molecular orbital with 60 π-electrons dictate the chemical reactivity. A very important aspect that was introduced with the investigation of fullerene chemistry is the shape dependence of reactivity.
Andreas Hirsch

Ring Opening Reactions of Fullerenes: Designed Approaches to Endohedral Metal Complexes

Endohedral complexes of fullerenes are some of the most attractive targets of research in fullerene chemistry and physics. An overview of the field is provided with a focus on endohedral complexes incorporating lanthanide metals, noble gases, and atomic nitrogen. Although the present approaches have been successful in providing the first members of this class of fullerenes, their preparation is still difficult and limited to a few elements. It is argued that ring opening reactions within fullerene shells have the potential to provide easy access to endohedral metallofullerenes on a large scale, including those with transition metals which are potentially the most interesting elements in regard to their materials properties. Current ring opening reactions within fullerene shells are reviewed. An outlook on ring opening reactions leading to effectively large apertures is presented.
Yves Rubin


The state of the art in heterofullerene chemistry and physics is reviewed with emphasis on azafullerenes. The macroscopic synthetic methods that have been developed for aza[60] fullerene compounds since 1995 have led to a whole new and rich area in the science of fullerenes: cage modification chemistry. The synthetic routes towards aza[60]fullerene and its derivatives are reviewed in Sect. 2. The synthetic routes for aza[70]fullerene and its derivatives are summarized in Sect. 3. Section 4 comprises the theoretical and experimental work on the physicochemical properties of azafullerene compounds. Finally, in Sect. 5, the literature regarding heterofullerenes other than monoazafullerenes is reviewed.
Jan C. Hummelen, Cheryl Bellavia-Lund, Fred Wudl

The Higher Fullerenes: Covalent Chemistry and Chirality

Many higher fullerenes, including some of their isomers, can be separated by high performance liquid chromatography (HPLC) on a number of stationary phases, a remarkable fact in view of the similarity of the carbon spheroids which differ mainly in shape and electronic properties of their π-systems, in addition to slight variations in size. Except for C70, which is available in preparative amounts from fullerene soot extract without tedious HPLC purification and has been derivatized in many ways, most separations of the larger carbon spheroids are limited to the milligram scale and require a multistep chromatographic purification. Furthermore, taking into account the relatively small amounts of these carbon cages contained in fullerene soot, the availability of pure higher fullerenes has remained the bottleneck in the field of their multifaceted chemistry. Still, a number of pure adducts of C76, C78 and C84 has now been isolated and characterized, and reactivity as well as regioselectivity principles begin to emerge for the higher fullerenes.
Another fascinating aspect of this research is the chirality of many higher fullerenes and numerous derivatives of chiral as well as achiral parent cages. It can originate from different structural characteristics of the spheroids and has led to the formulation of a new and simple configurational descriptor system. The study of chiral fullerenes and derivatives with a chiral functionalization pattern, initiated by the isolation and characterization of (±)-D 2-C76, constitutes the central topic of the present review. Following the successful resolution of C76 by two different methods, the structural assignment of its enantiomers became possible through comparison of the experimental to calculated circular dichroism spectra.
Carlo Thilgen, François Diederich

Fullerene Materials

The range of potential applications of fullerenes and fullerene derivatives in materials science is becoming broader in virtue of the increased number of derivatives that are continuously produced. New opportunities arise from the combination of the fullerene properties with those of other classes of materials, such as polymers, electro- or photoactive units, liquid crystals, etc. In this article we will review the most recent achievements in this field.
Maurizio Prato

Nanotubes: A Revolution in Materials Science and Electronics

Nanotube theoretical and experimental research has developed very rapidly over the last seven years, following the bulk production of C60 and structural identification of carbon nanotubes in soot deposits formed during plasma arc experiments. This review summarises achievements in nanotube technology, in particular various routes to carbon nanotubes and their remarkable mechanical and conducting properties. The creation of novel nanotubules, nanowires and nanorods containing other elements such as B, N, Si, O, Mo, S and W is also reviewed. These advances are paving the way to nanoscale technology and promise to provide a wide spectrum of applications.
Mauricio Terrones, Wen Kuang Hsu, Harold W. Kroto, David R. M. Walton


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