title: Highly stable organic monolayers for reacting silicon with further functionalities: the effect of the C-C bond nearest the silicon surface.
abstract: Crystalline Si(111) surfaces have been alkylated in a two-step chlorination/alkylation process using various organic molecules having similar backbones but differing in their C-C bond closest to the silicon surface (i.e., C-C vs C=C vs C[triple bond]C bonds). X-ray photoelectron spectroscopic (XPS) data show that functionalization of silicon surfaces with propenyl magnesium bromide (CH3-CH=CH-MgBr) organic molecules gives nearly full coverage of the silicon atop sites, as on methyl- and propynyl-terminated silicon surfaces. Propenyl-terminated silicon surface shows less surface oxidation and is more robust against solvent attacks when compared to methyl- and propynyl-terminated silicon surfaces. We also show a secondary functionalization process of propenyl-terminated silicon surface with 4'-[3-Trifluoromethyl-3H-diazirin-3-yl]-benzoic acid N-hydroxysuccinimide ester [TDBA-OSu] cross-linker. The Si-CH=CH-CH3 surfaces thus offer a means of attaching a variety of chemical moieties to a silicon surface through a short linking group, enabling applications in molecular electronics, energy conversion, catalysis, and sensing.
authors.affiliation: The Department of Chemical Engineering and Russell Berrie Nanotechnology Institute, Technion-Israel Institute of Technology, Haifa 32000, Israel.
authors.forename: Sreenivasa Reddy
authors.initials: SR
authors.lastname: Puniredd
authors.forename: Ossama
authors.initials: O
authors.lastname: Assad
authors.forename: Hossam
authors.initials: H
authors.lastname: Haick
mesh_terms: D002244:Carbon / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D010084:Oxidation-Reduction; D012825:Silicon / Q000737:chemistry*; D013053:Spectrophotometry; D013499:Surface Properties
chemical_list: D002244:Carbon; D012825:Silicon