Supramolecular chemistry features the study of molecular constituents that self-assemble into a specific complex directed by intermolecular forces (e.g. hydrogen bonding, hydrophilic/hydrophobic effects, metal-ligand coordination) between the functional groups within the overall structure. This type of self-assembly to form functional networks is exhibited in many biological structures, such as the actin and myosin filaments that control muscle movements, and building functional molecular networks using organic synthesis could be a useful tool to create new materials. Supramolecular complexes have been extensively studied for a diverse range of applications, including controlling chemical reactions, since supramolecular structures have been demonstrated to encapsulate guest molecules (e.g. catalysts) and release them in response to an applied stimulus. The main objective of our research is to functionalize a metal-ligand coordinated supramolecular capsule, such that it can be integrated into a polymer network for further applications in engineering stimuli-responsive biomimetic polymers or designing capsules for controlling chemical reactions. The supramolecular cluster developed by our group is a functionalized version of the Raymond group’s M4L6 tetrahderon; however, we have utilized a novel synthetic route to optimize the capsule for appending into a polymer network. The synthesis of the ligand uses commercially-available 2,3-dimethoxybenzoic acid and 1,5-diaminonapthalene as starting materials and employs a series of amide bond coupling and protection/deprotection reactions. The final phase of the synthesis involves the self-assembly of the metal-ligand cage itself with gallium (III) acetylacetonate (Ga(acac)3) and a copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction that will click the terminal alkyne on the capsule to the azide on a polymer of choice. Results from our work will be useful for a variety of applications, including the development of new stimuli-responsive polymers and materials inspired by mimicry of biological function.

Synthesis of a functionalized metal-ligand-coordinated supramolecular capsule for appending into polymers

251st National Meeting (2016)

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