The 1996 Nobel Prize for Chemistry has been won by Harold W. Kroto, Robert F. Curl and Richard E. Smalley for their discovery in 1985 of a new allotrope of carbon, in which have the structure of a truncated icosahedron and the atoms are arranged in closed shells. The new molecule was similar to geodesic domes designed by the architect Buckminster Fuller, therefore it was named Buckminsterfullerene.
Fig.1. Fullerene with different shapes
A fullerene is a molecule of carbon in the form of a hollow sphere, ellipsoid, tube, and many other shapes. Spherical fullerenes, also referred to as Buckminster fullerenes or buckyballs, whose structure resemble football. Cylindrical fullerenes are also called carbon nanotubes (buckytubes). Fullerenes are similar in structure to graphite, which is composed of stacked graphene sheets of linked hexagonal rings. Unless they are cylindrical, they must also contain pentagonal (or sometimes heptagonal) rings.
Structures and properties
Typical C60 fullerenes consist of 20 hexagonal and 12 pentagonal rings as the basis of an icosohedral symmetry closed cage structure. Each carbon atom is bonded to three others and is sp2 hybridised. Another fairly common fullerene is C70, but fullerenes with 72, 76, 84 and even up to 100 carbon atoms are commonly obtained (Fig 2).
Fig.2. The major isomers of fullerenes
Aromaticity: C60 is not "superaromatic" as it tends to avoid double bonds in the pentagonal rings, resulting in poor electron delocalisation. As a result, C60 behaves like an electron deficient alkene, and reacts readily with electron rich species.
Reactivity: Fullerenes are stable, but not totally unreactive. The sp2-hybridized carbon atoms, which are at their energy minimum in planar graphite, must be bent to form the closed sphere or tube, which produces angle strain. The characteristic reaction of fullerenes is electrophilic addition at 6,6-double bonds, which reduces angle strain by changing sp2-hybridized carbons into sp3-hybridized ones.
Solubility: Fullerenes are sparingly soluble in many solvents. Common solvents for the fullerenes include aromatics, such as toluene, and others like carbon disulfide. Solutions of pure buckminsterfullerene have a deep purple color. Solutions of C70 are a reddish brown. The higher fullerenes C76 to C84 have a variety of colors.
Chirality: Some fullerenes (e.g. C76, C78, C80, and C84) are inherently chiral because they are D2-symmetric, and have been successfully resolved. Many researches are ongoing to develop specific sensors for their enantiomers.
Fullerenes have been extensively used in materials science, electronics, and nanotechnology, especially in several biomedical applications including the design of high-performance MRI contrast agents, X-Ray imaging contrast agents, photodynamic therapy and drug and gene delivery.