Electrochemical charging of a fullerene-functionalized self-assembled monolayer on Au(111)

A fullerene derivative 10 with a terminal thiol group dissolves easily in common organic solvents and forms a densely packed self-assembled monolayer on gold surfaces. The functionalization of C-60 is based on the 1,3-dipolar cycloaddition of the azomethine ylide generated in situ from the corresponding aldehyde and N-methylglycine. The monolayers were characterized by grazing angle reflectance FTIR spectroscopy, scan tunneling microscopy, and cyclic voltammetry. The cyclic voltammogram of a SAM of 10 showed two well-resolved reversible cathodic waves corresponding to the first two one-electron reductions of the fullerene fragment.