Surface-Triggered Tandem Coupling Reactions of Cyclic Azasilanes

Cyclic azasilanes have been synthesized for the purpose of developing coupling agents appropriate for a variety of nanotechnologies including surface modification of nanoparticles, nanocrystals, mesoporous materials and substrates. N-methyl-aza-2,2,4-trimethylsilacyclopentane is representative of this class of compounds. Preliminary data for the treatment of inorganic surfaces, including nanoparticles and oxidized silicon wafers, with cyclic azasilanes suggest high density monolayer deposition by a ring-opening reaction. Cyclic azasilanes contain cryptic amine functionality that can perform a subsequent 'tandem' coupling reaction with functional molecules after the surface triggered ring-opening reaction, allowing for a one-pot self-assembly route on nanostructures. Tandem coupling reactions are demonstrated via addition reactions of the cryptic amine with epoxy and acrylate systems.