Self-assembled organosilane monolayers on silica surfaces find many applications
however, their structural characterization is challenging. We found that organic molecules in these monolayers can be dissociated from the surface by cleaving C-Si bonds under mild conditions of Fleming-Tamao oxidation. Once removed from the surface, the monolayer molecules could be isolated, purified, and analyzed in solution using conventional analytical techniques including NMR and GC-MS. This method enables efficient cleavage of different organic molecules attached to silica supports (e.g., in mixed monolayers) and is tolerant to a wide range of functional groups. Organic monolayers can be dissociated from a range of silica substrates, including silica nanoparticles, silica gel, flat glass slides, and related inorganic oxides, such as alumina or titania.