Applications of triazine chemistry: education, remediation, and drug delivery

Triazine chemistry has many applications from industrial usage, such as melamine resins, to academic interests in dendritic structures which may one day come to fruition as pharmaceutically applicable molecules. Organic synthesis, using the 1,3,5- triazine derivative 2,4,6-trichlorotriazine, cyanuric chloride, for practical applications was investigated. By utilizing the selective reactivity of cyanuric chloride, a plethora of targets from small molecules to large dendrimers may be synthesized. Triazine chemistry was adapted to an educational application for the development of an undergraduate laboratory to synthesize simazine, a widely used herbicide. The laboratory was designed to foster a sense of the applications of chemistry in the world and its effect on the environment and society. The modification of chitosan for herbicide remediation has been accomplished using triazine chemistry, as well. Treatment of chitosan iteratively with cyanuric chloride followed by piperazine produces dendritic grafts from these flakes. Dendrons of generation one through three were synthesized on chitosan backbones of low, medium, and high molecular weights. The piperazine derivatives were shown to sequester more than 99% of atrazine from an aqueous 100 ppb solution in a 24 h period. Drug delivery applications of triazine-based dendrimers were investigated. Pegylated G3 dendrimers with molecular weights of 18 and 34 kDa with 9% and 17% iodine content by weight, respectively, were synthesized as potential macromolecular contrast agents. The development of macromolecular contrast agents is of great interest to counteract the drawbacks associated with currently used, small molecule contrast media, including toxicity, extravasation into the extracellular space, and rapid clearance from the bloodstream. Dendrimers are well suited for use as macromolecular media due to the unique properties of these molecules, including monodispersity and multivalency.