Synthetic challenges in opening a large orifice on the surface of fullerene C60

ORGN 38

Yves Rubin, rubin@chem.ucla.edu, Shih Ching Chuang, schuang@chem.ucla.edu, and Shaohua Huang, shaohua@chem.ucla.edu. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569
We have been using “molecular surgery” approaches to insert atoms or small molecules inside fullerenes. However, larger species such as the transition metals cannot yet be incorporated because the size of the orifice achieved through chemical transformations has remained small. One of the possible mechanisms to obtain a sizeable orifice relies on the challenging three-fold σ-bond scission of a fully saturated six-membered ring of C60 via concerted [2+2+2] ring opening. The 1,2,3,4,5,6-hexaadducts required to test this mechanism were until recently unknown. We will describe recent work that has provided the first examples of these derivatives and the reactivity of these 1,2,3,4,5,6-hexaadducts towards ring scissions.

 

Novel Fluorophores
1:00 PM-5:30 PM, Sunday, April 6, 2008 Morial Convention Center -- Rm. R05, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008