Thioacetate-Functionalized Fullerene: Redox Properties and Self-Assembly on the Au(111) Surface

C-60 molecules have been functionalized according to the Prato method with the short S-acetyl-protected chains. The redox properties of this fullerene derivative in the solution reveal reversible 1e reduction - oxidation steps similar to those of C-60 but shifted to more negative potentials. The in situ deprotected fullerenethioacetate compound forms a stable uniform electroactive monolayer on the (111) surface of gold with the most common diameter of the molecule in range 1.4 +/- 0.2 nm. It undergoes both stepwise electroreduction playing the role of an efficient electron acceptor and electrooxidation to radical cation at highly positive potentials. This indicates that fullerenethioacetate formed ordered SAMs while maintaining the unique electronic properties of C-60 molecules. (C) 2012 The Electrochemical Society. [DOI: 10.1149/2.044301jes] All rights reserved.