This report describes the reactivity of acid fluoride (AF)-terminated self-assembled monolayers (SAMs) on goldtoward amine and alcohol compounds and the potentiality of AF as a reactive intermediate for surface functionalizations.The AF group was generated in situ on a gold surface by reacting the terminal carboxylic acid group in the SAMof 16-mercaptohexadecanoic acid with cyanuric fluoride and pyridine under the optimized conditions. AF was foundto be highly reactive toward various amine groups, such as primary and secondary amines, but it did not reacteffectively with alcohol. In addition, the amide coupling reaction by microcontact printing (
CP) was compared withthe solution-based reaction: when amine-derivatized ferrocene compound was used for 1-min
CP on the AF-activated surface, the surface coverage of the reaction product was about 83% of 3.45 × 10
14 cm
-2, the coverageobtained in the solution-based reaction. On the basis of the high reaction efficiency of
CP, the AF-activated surfacewas also used as a platform for patterning a biological ligand, biotin.