Date of Award
2025
Document Type
Thesis
Terms of Use
© 2025 Stephen Kwas. All rights reserved. This work is freely available courtesy of the author. It may only be used for non-commercial, educational, and research purposes. For all other uses, including reproduction and distribution, please contact the copyright holder.
Degree Name
Bachelor of Arts
Department
Chemistry & Biochemistry Department
First Advisor
Anna Yang
Abstract
Tubular structures are ubiquitous in nature and possess functions ranging from the structural ones played by microtubules to transporting necessary ions across cell membranes by membrane proteins. In addition, the excellent electronic and structural properties of carbon nanotubes have made them of great interest to chemists. Yet, the functionalization of these nanotubes is hindered by unselective post-modification, often requiring harsh reaction conditions. As such, the assembly of macrocycles into nanotubular structures has been widely studied by chemists. One such way to make these materials is by using dynamic, reversible reactions to synthesize pyridine-containing macrocycles in high yields. Due to inherent strength of carbon-carbon bonds, the Yang Group is interested in synthesizing pyridine-containing macrocycles using dynamic alkyne and dynamic olefin metathesis. Despite the advantages offered by both of these reactions, they are ultimately limited by their poor tolerance of Lewis basic groups like pyridine.
This thesis explores the synthesis of these macrocycles from two different approaches. First, I investigate the origins of a catalyst deactivation by pyridinyl substrates during alkyne metathesis using small molecule test substrates. I suggest that the product of alkyne metathesis on pyridinyl substrates plays a critical role in deactivating the catalyst. I then continue to use these small molecule test substrates to test various ways to overcome this low reactivity. Second, I apply the findings from my small molecule test reactions to synthesize pyridine-containing monomers for alkyne or olefin metathesis. The results from this thesis provide a guide for the synthesis of metathesis-compatible monomers, which will be explored further by the Yang Group.
Recommended Citation
Kwas, Stephen , '25, "Progress toward the synthesis of pyridine-containing macrocycles using dynamic alkyne and olefin metathesis" (2025). Senior Theses, Projects, and Awards. 978.
https://works.swarthmore.edu/theses/978