Production of Perfluoroalkylated Nanospheres from Buckminsterfullerene

Perfluoroalkylated nanospheres have been prepared by reaction of fullerenes with a variety of fluoroalkyl radicals. The latter are generated by thermal or photochemical decomposition of fluoroalkyl iodides or fluorodiacyl peroxides. Up to 16 radicals add to C60 to afford easily isolable fluoroalkylated derivatives. The monosubstituted radical adducts were detected by electron spin resonance in the early stages of the fluoroalkylation reactions. These spheroidal molecules are thermally quite stable, soluble in fluoroorganic solvents, chemically resistant to corrosive aqueous solutions, and more volatile than the parent fullerenes. Films of the sublimed material display properties typical for a perfluoroalkylated material.

[1]  D. Chase,et al.  Synthesis and Single-Crystal X-ray Structure of a Highly Symmetrical C60 Derivative, C60Br24 , 1992, Science.

[2]  Weaver,et al.  Electronic structure of highly fluorinated C60. , 1993, Physical review. B, Condensed matter.

[3]  T. Nakajima,et al.  Chemical bonding and electrochemical reduction of fluorinated fullerene , 1992 .

[4]  E. Campbell,et al.  Transfer Hydrogenation and Deuteration of Buckminsterfullerene C60 by 9,10‐Dihydroanthracene and 9,9′,10,10′[D4]Dihydroanthracene , 1993 .

[5]  D. Griller,et al.  Homolytic addition to benzene. Rate constants for the formation and decay of some substituted cyclohexadienyl radicals , 1981 .

[6]  B. Parkinson,et al.  Electron spin resonance study of the radical reactivity of C60 , 1991 .

[7]  E. Wasserman,et al.  ESR studies of the reaction of alkyl radicals with fullerene (C60) , 1992 .

[8]  K. Preston,et al.  Radical Reactions of C60 , 1991, Science.

[9]  P. Krusic,et al.  The proton hyperfine interaction in HC60, signature of a potential interstellar fullerene , 1993 .

[10]  W. Krätschmer,et al.  Solid C60: a new form of carbon , 1990, Nature.

[11]  E. Johnston,et al.  EPR study of hindered internal rotation in alkyl-fullerene (C60) radicals , 1993 .

[12]  Yitzhak Apeloig,et al.  The chemistry of organic silicon compounds , 1989 .

[13]  E. Wasserman,et al.  The dimerization of fullerene RC60 radicals [R = alkyl] , 1992 .

[14]  R. Hettich,et al.  Characterization and stability of highly fluorinated fullerenes , 1992 .

[15]  Michael M. Haley,et al.  Efficient production of C60 (buckminsterfullerene), C60H36, and the solvated buckide ion , 1990 .

[16]  Y. Rubin,et al.  Characterization of the soluble all-carbon molecules C60 and C70 , 1990 .

[17]  J. Adcock,et al.  Hyperfluorination of buckminsterfullerene: Cracking the sphere , 1993 .

[18]  R. Strongin,et al.  Fluorinated fullerenes: synthesis, structure, and properties , 1993 .