Molecular Recognition with 2,4-Diaminotriazine-Functionalized Colloids

New polymeric colloids functionalized with 2,4-diaminotriazine residues have been prepared. The functionalities provide a triple hydrogen bond motif with a donor acceptor donor (DAD) pattern. The colloids are based on cross-linked poly-4-methoxymethyl styrene and are polymerized by means of surfactant-free emulsion polymerization. The reaction pathway including five steps was successfully tracked and verified via C-13 CP/MAS solid-state NMR. Characterization of the colloids was done by combined static and dynamic light scattering and indicates a compact spherical particle shape. In solvents with the appropriate polarity, intercolloidal hydrogen bonding was enabled, including colloidal aggregation. In highly dilute solutions of THF, this aggregation was recordable by means of time-resolved static light scattering experiments. If THF was saturated with uracil, then aggregation could be completely inhibited. Uracil bears a triple hydrogen bond motif of the form acceptor donor acceptor (ADA) and is a direct antagonist of 2,4-diaminotriazine. The charging of the colloids with uracil via hydrogen bond formation as a typical molecular recognition mechanism could be confirmed by IR spectroscopy.