Brian J. Knight, N. Martín, T. Ohno
Oct 15, 1997
Citations
0
Influential Citations
63
Citations
Journal
Journal of the American Chemical Society
Abstract
Spiroannelated methanofullerenes bearing quinone-type addends including TCNQ and DCNQI analogues (3a−c, 6a,b, 8, 10, and 11) have been prepared, and their structural and electronic properties have been characterized by both experimental techniques and quantum-chemical calculations. The spiro[2,5-cyclohexadienone-4,61‘-methanofullerene] derivatives (3a−c), the spiro[10-anthrone-9,61‘-methanofullerene] (8), and the TCNQ- and DCNQI-type derivatives (10 and 11) were isolated as [6,6] adducts. The spiro[cyclohexanone-4,61‘-methanofullerene] (6) was however obtained as a mixture of [5,6] and [6,6] isomers. The novel methanofullerenes, with the only exception of 6, show irreversible cyclic voltammograms with additional reduction peaks. The conjugated cyclohexadienone derivatives 3 exhibit better acceptor abilities than the parent C60. Semiempirical PM3 calculations show that the addend lies perpendicular to the transanular bond in 3, while it folds down and adopts a butterfly shaped structure for compounds 8, 10...