This paper reports 16 chemical reactions for elaborating the structures of self-assembled monolayers (SAMs) of alkanethiolates on gold. This work takes advantage of matrix-assisted laser desorption/ionization and time-of-flight mass spectrometry (MALDI-TOF MS) to rapidly characterize the products and yields of reactions that occur with molecules attached to monolayers. The paper also describes a method for screening reaction conditions, wherein monolayers are treated with an array of reactants and mass spectrometry is used to identify those regions that undergo reactions to give new, and unanticipated, products in high yield. These examples serve to increase the collection of reactions that can be used to elaborate the structures, and therefore the properties, of self-assembled monolayers of alkanethiolates on gold and to introduce label-free methods for screening interfacial reactions.
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