Trialkoxyheptazine-Based Glyconanoparticles for Fluorescence in Aqueous Solutions and on Surfaces via Controlled Binding in Space

The fluorescent organic 2,5,8-tris((adamantan-1-yl) methoxy)-heptazine (HTZ-Ad) was solubilized in water by inclusion of adamantane groups into free β-cyclodextrins or cyclodextrin shell of glyconanoparticles. These glyconanoparticles with average diameters between 40 and 60 nm result from the self-assembly of polystyrene-block-β-cyclodextrin copolymer. Under UV irradiation at 365 nm, the modified nanoparticles exhibit fluorescence emission in aqueous media as well as in their adsorbed state. This constitutes the first spectroscopic characterization of a trialkoxyheptazine in aqueous medium. The specific binding of the glyconanoparticles to a surface was achieved via host-guest interactions with an electrochemically generated poly(pyrroleadamantane) film. An interdigitated microelectrode modified with poly(pyrrole-adamantane) film and glyconanoparticles was incubated in HTZ-Ad resulting in a substrate with spatially controlled fluorescence. The same modified electrode was incubated with an aqueous suspension of glyconanoparticles previously functionalized by HTZ-Ad, resulting in a fluorescent 3D assembly.