Novel chemistry of elemental carbon: Graphite, fullerenes and nanotubes

The goal of this work was to examine the chemistry that one can do with various fluorinated forms of elemental carbon. As a prelude to the experimental worked out for this thesis, a brief discussion of the various allotropic forms of carbon is given followed by a brief discussion of elemental fluorine and fluorination procedures. Graphite fluorides have been defluorinated with ammonia, trimethyl amine and hydrazine and functionalized with organolithium species to give soluble, submi sized graphitic particles. C₆₀ has been fluorinated to yield C₆₀F_n species which n is predominately 42–46. These fluorinated fullerenes were then reacted with organolithium species to yield highly alkylated species having properties which differed greatly from C₆₀ or their fluorinated counterparts. While the fluorination of graphite and fullerenes has been reported before, the fluorination of single wall carbon nanotubes (SWNTs) has not. The first report of the fluorination of SWNTs is described here as is our finding that hydrazine can defluorinate the “fluorotubes” to regenerate the original SWNTs. It was also determined that the fluorotubes were soluble in alcohol solvents and that reactions could be carried out on them while in solution. Using a technique which we developed here at Rice called “Ultrasonic assistance,” we were able to react the fluorotubes with organolithium species in solution to yield alkylated SWNTs which could then be isolated by filtration and dissolved in chloroform.