Patterning Ligands on Reactive SAMs by Microcontact Printing

This report describes a method for patterning ligands onto mixed SAMs of alkanethiolates on gold by microcontact printing (μCP). The mixed SAMs were made from thiols presenting terminal tri(ethylene glycol) groups (HS(CH2)11(OCH2CH2)3OH, 1) and terminal hexa(ethylene glycol)−CH2CO2H groups (HS(CH2)11(OCH2CH2)6OCH2CO2H, 2). Ligands were printed using a two-step procedure. The carboxylic acid groups of 2 were first converted to reactive pentafluorophenyl esters. A freshly oxidized PDMS stamp, inked with a ligand derivatized with a primary amine, was then brought into contact with the activated SAM; in the areas of contact, the amine reacted with the activated ester and formed an amide. Two ligands, biotin and benzenesulfonamide, were printed onto these SAMs. The formation of patterned SAMs presenting biotin ligands was detected by fluorescence microscopy of substrates that were incubated with a solution of fluorescently labeled antibiotin antibody. The formation of patterned biotin was also detected using a...