Structural (im)perfection in antibacterial oligomers

Zhou, Zhe
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Palermo, Edmund
Ullal, Chaitanya
Ozisik, Rahmi
Bae, Chulsung
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Materials engineering
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In this dissertation, we designed a fully abiotic way to synthesize discrete unimolecular weight polyolefins by using a molecular template. We synthesized discrete and unimolecular oligo(thiophene)s template with alternating sequence by iterative convergent/divergent couplings and then pendant cyclic olefin monomers are attached in the side chains. Once the Grubbs third-generation catalyst loaded in dilute DCM solution, the attached monomers underwent templated ring-opening metathesis (TROM). Then, we liberated the daughter olefin from the parent template by hydrolysis. Cyclooctenes underwent TROM to generate macrocyclic polyolefins that exactly replicate the template’s chain length. As a comparison, we treated norbornene attached template molecules in the same TROM condition, which formed linear products with styrenic groups at the chain end. Then a heterogenous template, which contains one norbornene monomer at the α chain end followed five cyclooctene monomers along the template, was synthesized. The heterogenous template molecule was treated under same TROM condition to afford the macrocyclic daughter olefin. Intertemplate metathesis can be controlled by adjusting the reaction time and concentration.
May 2020
School of Engineering
Dept. of Materials Science and Engineering
Rensselaer Polytechnic Institute, Troy, NY
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