ORGN 591 |
| Tao Gu, James K. Whitesell, and Marye Anne Fox. Department of Chemistry, North Carolina State University, Raleigh, NC 27695 |
| 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 C60 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. A self-assembled monolayer of 10 on gold exhibited a GAR-FTIR spectrum indicative of aromatic rings of the C60 and diphenylacetylenes perpendicular to the Au surface. Electrochemical measurements showed that the surface-confined self-assembled monolayer of 10 exhibits ideal behavior (for the first and second one-electron reduction) because of softly packed alkoxy chains permit easy penetration of counter ions into the preformed monolayer. STM demonstrates a high coverage of surface-confined fullerene-alkylthiol 10. |
|
Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Thursday, April 1, 2004 Anaheim Convention Center -- 303A, Oral
Division of Organic Chemistry |
