dc.description.abstract | 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. | en |