CUR - The Council on Undergraduate Research

Separation and isolation of [6,6]-closed epoxide derivative of fullerene using semi-preparative high performance liquid chromatography

Mitzy Garner, Jesse Ingham, and Dr. Rangika Hikkaduwa Koralege, Department of Chemistry and Physics, Western Carolina University, 1 University Way, Cullowhee NC 28723

Due to wide spread applications and commercialization of fullerene (C60), both human and environmental systems become increasingly exposed to these materials. Although fullerene has negligible solubility in water, the ability to form stable aqueous colloids (known as nano-C60 or nC60) and the availability of these in natural systems at environmentally-relevant concentrations led to the studies of its toxicity. It has been demonstrated that the key component of these fullerene colloids that allows water stability is a derivative of fullerene known as [6,6]-closed epoxide or C60O.  Previous studies have indicated that the colloidal suspensions of fullerene can induce oxidative stress in living systems. Our final goal in this research is to determine the effect of C60O in the oxidative behavior of these colloids. The major focus of this project is to separate and isolate the C60O using semi-preparative high performance liquid chromatography (HPLC). Ozonation of C60 dissolved in toluene produces a mixture of fullerene and various fullerene oxides. Semi-preparative HPLC has been used to separate these compounds and isolate the [6,6]-closed epoxide and ultraviolet-visible spectroscopy has been used to confirm the isolated compounds. Excellent peak separation has been achieved, between C60, C60O, and C60O2 by using a mixture of toluene/n-hexane mobile phase in a Nacalai Cosmosil Buckyprep packed semi-preparative column. Isolated C60O has been used to prepare aqueous colloidal suspensions of C60O for further experimentation and we are currently working on characterizing these colloidal suspensions.

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