Of Buckminsterfullerene

Sun Y-P, Wang P and Hamilton N B 1993 Fluorescence spectra and quantum yields of Buckminsterfullerene (Cgg) in room-temperature solutions. No excitation wavelength dependence J. Am. Chem. Soc. 115 6378-81... 

Suzuki, T. Li, Q. Khemani, KC. Wudl, F. Almarsson, O. Systematic Inflation of Buckminsterfullerene CgQi Synthesis of Diphenyl Fulleroids Cgj to Cgg Science, 254 1186-1188, 1991. 

Since the discovery of buckminsterfullerene (C o) [85NAT(318)162] and other fullerenes (Cig. C70), these molecules have been intensely studied, both experimentally and theoretically. Likewise, several reports on heterofullerenes containing heteroatoms such as nitrogen and boron have appeared (91JPC4948 91JPC10564). The incorporation of heteroatoms is expected to modify the structural and electronic features of these structures, and have thus attracted some interest. 

Chemists were greatly surprised when soccer-ball-shaped carbon molecules were first identified in 1985, particularly because they might be even more abundant than graphite and diamond The C60 molecule (10) is named buckminsterfullerene after the American architect R. Buckminster Fuller, whose geodesic domes it resembles. Within 2 years, scientists had succeeded in making crystals of buckminsterfullerene the solid samples are called fullerite (Fig. 14.32). The discovery of this molecule and others with similar structures, such as C70, opened up the prospect of a whole new field of chemistry. For instance, the interior of a C60 molecule is big enough to hold an atom of another element, and chemists are now busily preparing a whole new periodic table of these shrink-wrapped atoms. 

C14-0135. S ° of graphite is 3 times larger than S ° of diamond. Explain why this is so. (You may need to review the structures and properties of graphite and diamond in Section 11-.) Buckminsterfullerene is a solid that consists of individual molecules with formula Cgo. Is the molar entropy of buckminsterfullerene larger or smaller than that of graphite How about the entropy per gram Explain. 

Of all the fullerene forms, the nearly spherical properties of C o have attracted the greatest attention, especially in the field of bioconjugation. In addition to its physical properties, C o fullerenes have unique photo-optical and electro-chemical properties, which make them useful as carriers for biomedical research applications. For instance, upon exposure to light C o will generate singlet oxygen, which can be used in vivo to cleave biological molecules, particularly DNA and RNA. Studies indicate that irradiation of Cgo in solution can be used to destroy virus contamination (Kasermann and Kempf, 1997). Solutions of Buckminsterfullerene are a deep purple color, whereas other sizes of fullerenes display a variety of other colors. 

FIGURE 13.13 The structure of buckminsterfullerene, C60.The structure consists of five- and six-membered rings. 

Yang SH, Pettiette CL, Conceicao CJO, Smalley RE (1987) UPS of buckminsterfullerene and other large clusters of carbon. Chem Phys Lett 139 233-238... 

L. Isaacs, R. E Haldimann, F. Diederich, Tether-directed Remote Functionalization of Buckminsterfullerene Regiospecific Hexaadduct Formation , Angew. Chem. Int. Ed. Engl. 1994,33, 2339-2342. 

W. Y. Qian, Y. Rubin, Towards Sixfold Functionalization of Buckminsterfullerene (Qo) at Fully Addressable Octahedral Sites Angew. Chem Int. Ed. Engl. 1999, 38, 2356-2360. 

Shibuya M, Kato M, Ozawa M et al. (1999) Detection of buckminsterfullerene in usual soot and commercial charcoals. Full Sci Technol. 7 181-193. 

Steele et al. [28] have measured the standard enthalpy of combustion of buckminsterfullerene Ceo with bomb calorimetry of solid samples at 298.15 K. They have found a value of 26,033 + 14kJ mol Calculate the standard enthalpy of formation of Ceo and the standard enthalpy of transition from graphite to Cgo-... 

The preceding section indicated the importance of corannulene as the smallest member of the family of bowl-shaped, polynuclear aromatic hydrocarbons modeling the surface of buckminsterfullerene. Surprisingly, despite its obvious significance in relationship to the theory of aromaticity, 8 had not attracted the attention of chemists prior to the first report of its synthesis in 1966." As Barth and Lawton noted ... to the time of our first report, it appears this structure had neither adoriied the jacket or end cover of any book nor served as a symbol of an international symposium. More than that, corannulene does not appear to have been suggested in the chemical literature prior to 1966. 

The chemistry of curved, polynuclear aromatic hydrocarbons holds great promise due, in part, to the rampant interests in fullerenes. Of special interest, of course, is their relationship to the fullerenes, and these compounds should serve as good models in many ways since the curvature of the systems already known matches that of buckminsterfullerene, at least at the point of maximum curvature. 

Aldersey-Williams, JJugh. The Most Beautiful Molecule The Discovery of the Buckyball. New York Wiley, 1995. Scientific discoveries are often based on a complicated series of events. This book tells the lively tale of the discovery of buckminsterfullerenes (also known as buckyballs), and discusses their potential applications. 

What is the symmetry of buckminsterfullerene934 Do you expect it to be chiral To have a dipole moment To be soluble in benzene Buckminsterfullerene was named after R. Buckminster Fuller, who became best known for his popularization of the geodesic dome Is a geodesic dome the same as a segment of buckminsterfullerene What is the symmetry of the bis(4-r-butyIpyridine)osmyl derivative of buckminsterfullerene (Fig. 3.34) Do you expect it to be chiral To have a dipole moment To be soluble in benzene ... 

A similar outline drawing for the construction of buckminsterfullerene has been published.2 Several other polyhedral models constructed from simple materials have been described in a series of articles.3... 

Hydrosilylations of buckminsterfullerene (Cgo) with a poly(hydrosiloxane) (301) or H(SiMe20)3SiMe2H in the presence of Karstedt s catalyst (vide supra) proceed smoothly at 29 °C to give the corresponding (1 1) Cgo-polysiloxanes (302) with molecular weights of 5000 and 4000, respectively (equation 112)297. 

Fullerenes, Cxy, have internal cavities that can act as containers for metal atoms. The metal reduces Cxy and is trapped in a fullerene cage (Saalfrank 1996). For example, Buck-minsterfullerene C6o can react with two potassium atoms, producing a dianion diradical that is a triplet in its ground state. Alkali metal salts of Buckminsterfullerene C6o possess the highest superconductivity transition temperatures (Tc) to date for organic materials, e.g., K3C60 with Tc = 19 K, Rt Ceo with Tc = 29 K, and Cs2RbC60 with / , 33 K (Haddon... 

Ballenwey S, Gleiter R, Kratshmer W (1993) Hydrogenation of buckminsterfullerene c-60 via hydrozirconation - a new way to organofullerenes. Tetrahedron Lett 34 3737-3740... 

Busci I, Szabo P, Aniszfeld R, Surya Prakash GK, Olah GA (1998) HPLC separation of hydrogenated derivatives of buckminsterfullerene. Chromatographia 48 59-64... 

Aihara, J. Hosoya, H. 1988 Spherical aromaticity of buckminsterfullerene. Bull. Chem. Soc. Japan 61, 2657 2659. 

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