Progress Towards the Design and Synthesis of Vinyl-Sulfone Functionalized Polymers

Sophie Wazlowski

Sophie is a rising senior at Wesleyan double majoring in Chemistry and English. She joined the Northrop lab as a sophomore and has been researching the use of vinyl sulfone derivatives in both dendrimer and polymer synthesis. She grew up in New Fairfield, Connecticut and graduated from the High School Avenues: New York. At Wesleyan, Sophie writes for the Wesleyan Argus and the Individuals in STEM site, in addition to serving as a TA for organic chemistry. After graduating, she hopes to work in Biotech before deciding to pursue graduate degrees in chemistry or business. Outside of the lab, she enjoys singing, running and creative writing.

Abstract: Ring-opening metathesis polymerization, or ROMP, is a reaction driven by the favorability of relieving ring strain which results in the opening of cyclic structures that contain an alkene. While ROMP has been used extensively to synthesize various types of polymers, there has been little exploration of cyclic alkenes containing vinyl sulfone derivatives. For this project, vinyl sulfonyl norbornene monomers were synthesized through Diels-Alder reactions. Cyclopentadiene and furan were used as dienes and reacted with numerous dienophiles: isopropoxy vinyl sulfone, n-butoxy vinyl sulfone, n-hexyloxy vinyl sulfone, ethyl vinyl sulfone, and phenyl vinyl sulfone. The synthesized structures were analyzed through ¹H NMR and 2D COSY NMR. Relative Gibbs transition state and reaction free energies were calculated using Gaussian16 optimizations performed at the M062x/6-311G(2d,p) level of theory. In the future, each of the norbornene products synthesized will be reduced to their thioether and sulfoxide forms. The resulting products will be used as monomers for ROMP to form various polymers, which are expected to have new and exciting properties.

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Summer-Research-2021

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