Since my sophomore year of undergraduate studies, I have been conducting research in Professor Dennis D. Cao’s organic materials lab at Macalester College. Since my debut in the lab, I have worked on two independent projects that encompass the areas of photocatalysis and supramolecular self-assembly.
Interest in supramolecular self-assembly has continued to grow exponentially within recent years. A notable surge in synthetic interest has grown towards the creation of novel and highly organized symmetric, porous structures, that may hold promise for the development of new materials to be used in diversified applications. The 1987 Nobel Prize-winning work of Donald J. Cram, Jean-Marie Lehn, and Fritz Vogtle, which demonstrated the ability of porous organic macrocycles (crown ethers) to engage in non-covalent, host-guest interactions with ions, has further fueled work in this field.
Macrocycles' unique and symmetric structures enable them to encapsulate other molecules within their structural cavity, and can be designed to bind with charged or neutral substrates. Resultantly, macrocycles offer a high level of specificity and selectivity, and are of keen interest for their use in diverse applications such as targeted drug delivery, gas adsorption, and organic electronics.
Through mentorship of Professor Dennis D. Cao (Macalester College), the focus of our project is to synthesize novel macrocycles by exploiting the 109° angle of sp3 carbons to direct the assembly of pentagonal shapes, which we believe possible since the interior angle of a pentagon is 108°.
At the heart of the project, we are employing dynamic covalent chemistries by exposing di-topic alkene monomers to alkene metathesis conditions with the hypothesis that pentagonal macrocycles will be thethermodynamically favored products of the metathesis equilibrium. Recently, we were excited to synthesize novel aforementioned macrocycle that features a cavity of about 14 Å in diameter, and obtained ground-breaking APCI-MS data that strongly supports our claim.
Additional reactions are currently being tested in order to optimize our processes, with the hope of submiting a manuscript for publication within the next year. I am currently working on optimizing the metathesis reactions, after which I expect to be the first author of a resulting manuscript and eventual publication within the next year.
Most notably, my abstract was accepted by the ACS, and as a result, will be traveling to the 255th American Chemical Society National Meeting this March in New Orleans, Louisiana, where I will be presenting his work and most recent findings at the Division of Organic Chemistry's poster session.