Tethered bisadducts of C60 and C70 with addends on a common hexagonal face and a 12-membered hole in the fullerene cage

J Am Chem Soc. 2015 Jun 17;137(23):7502-8. doi: 10.1021/jacs.5b03768. Epub 2015 Jun 4.

Abstract

The regioselective synthesis of easily isolable pure bismethano derivatives of C60 and C70 with high steric congestion is described using 1,3-dibenzoylpropane bis-p-toluenesulfonyl hydrazone as the addend precursor. When the addition occurs at two [6,6] ring junctions within the same hexagon, bisadducts with mirror symmetry are obtained for both C60 and C70. When the addition occurs at two [5,6] ring junctions in C60, a symmetrical adduct is formed, which readily undergoes photo-oxygenation and ring opening to yield a fullerene with a hole in the cage. In this work, we also propose a simple and general system to name all of the possible [6,6] bisadduct isomers on C70.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Fullerenes / chemistry*
  • Isomerism
  • Models, Molecular
  • Molecular Structure

Substances

  • Fullerenes