Orthogonal covalent and noncovalent functionalization of cyclodextrin-alkyne patterned surfaces.

The creation of cyclodextrin patterns on a fluorescent reporter surface by microcontact printing provides a versatile orthogonal surface modification method. The alkyne-beta-cyclodextrin surface is prepared through a "click" reaction on alkyne-terminated coumarin monolayers. The resulting alkyne-beta-cyclodextrin surface can be functionalized through supramolecular microcontact printing on cyclodextrin host patterns and by reactive microcontact printing-induced click chemistry on the alkyne-terminated patterns. The orthogonal covalent and supramolecular "host-guest" functionalization of the surface, and its specificity as well as selectivity, is demonstrated by sequential and one-step printing procedures.