Thiol functionalization of surfaces for biosensor development

The immobilization of biomolecules on substrate surfaces for biosensor development requires linking molecules that must meet a specific set of criteria. Two such agents based on bifunctional alkyltrichlorosilane structures, 1-bromo-11-(trichlorosilyl)-undecane and 1-(thiotrifluoroacetato)-11-(trichlorosilyl)-undecane, are employed to generate thiol-functionalized surfaces either by nucleophilic substitution followed by reduction (bromine-containing derivative) or deprotection (fluorine-containing compound). Both molecules have been attached to the surfaces of silicon wafers in conjunction with the diluent silane, octyltrichlorosilane. X-ray photoelectron spectroscopic analysis in the conventional and angle-resolved modes confirms that both silanization reactions were successful. The alkyl-bromine surfaces were subjected to treatment with a set of nucleophilic reactants followed by reduction and derivatization with trifluoroacetic anhydride. The latter in conjunction with surface analysis was used to estimate the level of thiol functionalization achieved. The fluorine-containing undecane surface has been studied by surface analysis both before and after deprotection of the thiol group by hydroxylamine solution. The results indicate that a high coverage of the surface was found for the protected moiety, with approximately 10% of the trifluoro acetate groups remaining after the deprotection procedure.