Redox-active Si(100) surfaces covalently functionalized with [60]fullerene conjugates: new hybrid materials for molecular-based devices

F. Cattaruzza, A. Llanes-Pallas, A. G. Marrani, E. A. Dalchiele, F. Decker, R. Zanoni, M. Prato, D. Bonifazi,
J. Mater. Chem. 2008, 18, 1570-1581
DOI: 10.1039/b717438a


Herein, we report the covalent immobilisation, through Si–C bonds, of various [60]fullerene derivatives on flat silicon surfaces following three different preparative protocols. Each synthetic strategy comprises a two-step approach that includes a pre-modification step of the Si(100) surface with an organic monolayer bearing a terminal functionality that undergoes a bond-forming reaction with a [60]fullerene synthon as characterized by X-ray photoelectron spectroscopy (XPS) measurements. Water contact angle measurements clearly showed a characteristic change of the surface hydrophobicity upon covalent immobilisation of the carbon functions. The hybrid [4b-Si(100)] surfaces, containing [60]fullerene-ferrocene fragments, were also investigated by means of cyclic voltammetry (CV), and were revealed to be exceptionally robust towards repeated reduction–oxidation cycles. Moreover, several surface-confined redox couples were observed in CH3CN solution. The surface coverage was measured to be ca. 2.5 × 10−11 mol cm−2.

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