Authors: Mackay B Steffensen, AustinRyan A Kirkby, Kieran L Richards
Mentors: Mackay B Steffensen
Insitution: Southern Utah University
Cyanuric chloride, a 1,3,5-trichlorotriazine, serves as a valuable platform for constructing innovative molecules. This project explores the unique reactivity of triazines to synthesize triazine crown ethers—a class of cyclic polyethers with a central cavity capable of selectively binding metal ions and polar molecules. Temperature-controlled nucleophilic aromatic substitution is employed to selectively substitute the triazine ring, providing precise control over the reaction. The first substitution with a primary amine nucleophile occurs rapidly at 0 °C, while subsequent substitutions at room temperature or 70 °C necessitate longer reaction times. This controlled approach enables the incorporation of three different amines.
The project aims to synthesize triazine crown ethers through temperature-dependent substitution using two different methods. The first approach employs a diamine with an ether linkage in the presence of a base, facilitating consecutive substitutions to produce the target molecule. Intramolecular reactions are favored, but intermolecular reactions may lead to unexpected yet valuable products. The second method utilizes templated synthesis, taking advantage of the affinity of crown ethers for metal cations to promote cyclization reactions. A traditional route involving post-synthetic cyclization with ethylene glycol is also considered.
The successful synthesis of these molecules opens up opportunities for further research, including characterizing their affinity for metals and exploring other unique properties. The acquired knowledge can be applied to construct more complex molecular structures, making this work valuable in materials science, analytical chemistry, and pharmaceuticals.