J. Am. Chem. Soc., 128 (49), 15793 -15798, 2006. 10.1021/ja065178l S0002-7863(06)05178-X
Web Release Date: November 14, 2006

Copyright © 2006 American Chemical Society

Trifluoromethyl Derivatives of Insoluble Small-HOMO-LUMO-Gap Hollow Higher Fullerenes. NMR and DFT Structure Elucidation of C2-(C74-D3h)(CF3)12, Cs-(C76-Td(2))(CF3)12, C2-(C78-D3h(5))(CF3)12, Cs-(C80-C2v(5))(CF3)12, and C2-(C82-C2(5))(CF3)12

Natalia B. Shustova, Igor V. Kuvychko, Robert D. Bolskar, Konrad Seppelt, Steven H. Strauss,* Alexey A. Popov,* and Olga V. Boltalina*

Contribution from the Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, Institut für Anorganische und Analytische Chemie der Freie Universität Berlin, Berlin D14195, Germany, TDA Research Inc., 12345 West 52nd Avenue, Wheat Ridge, Colorado 80033, and Chemistry Department, Moscow State University, Moscow 119992, Russia

steven.strauss@colostate.edu; popov@phys.chem.msu.ru; ovbolt@lamar.colostate.edu

Received July 19, 2006

Abstract:

Reaction of a mixture of insoluble higher fullerenes with CF3I at 500 C produced a single abundant isomer of C74(CF3)12, C76(CF3)12, and C80(CF3)12, two abundant isomers of C78(CF3)12 and C82(CF3)12, and an indeterminant number of isomers of C84(CF3)12. Using a combination of 19F NMR spectroscopy, DFT calculations, and the structures and spectra of previously reported fullerene(CF3)n compounds, the most-probable structures of six of the seven isolated compounds were determined to be specific isomers of C2-(C74-D3h)(CF3)12, Cs-(C76-Td(2))(CF3)12), C2-(C78-D3h(5))(CF3)12), Cs-(C80-C2v(5))(CF3)12), C2-(C82-C2(5))(CF3)12), and C2-(C82-C2(3))(CF3)12) containing ribbons and/or loops of edge-sharing para-C6(CF3)2 hexagons. The seventh isolated compound is a C1 isomer of C78(CF3)12 containing two such ribbons. This set of compounds represents only the second reported isolable compound with the hollow C74-D3h cage and the first experimental evidence for the existence of the hollow fullerenes C76-Td(2), C78-D3h(5), C80-C2v(5), and C82-C2(5) in arc-discharge soots.

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