Fluorinated saccharides on the Si(0 0 1) surface

The attachment of saccharide molecules directly to silicon surface has been for the first time. Oxygen free silicon surface was functionalized with monosacharides thanks to UV irradiation in acetonitryl solution (254 nm). Selected derivatives of pentofuranose were protected at the C-1 and C-2 position. The remaining hydroxyl group at C-3 or C-5 was suitable for direct attachment to H-terminated Si(0 0 1) surface via Sisingle bondOsingle bondC bonds. The binding energy of the saccharide to the Si surface was investigated by quantum mechanical calculations method. The Parametric Method 5 (PM5) calculations confirmed that the formation of Sisingle bondOsingle bondC bonds was chemically possible. Synthesis of new fluorinated carbohydrates has been described. The resulting monolayers were characterized by Atomic Force Microscopy (AFM), X-ray photoelectron spectroscopy (XPS) and Attenuated Total Reflection (ATR) infrared spectroscopy. The effect of incorporating fluorine atom or CF3 group into self-assembled monosaccharide monolayers was studied using a water contact angle measurements. The resulting surface wettability of different fluorinated components on one kind of planar substrate enables an answer which of derivative is required for the preparation of the hydrophobic monolayer.