Date of Award

Summer 2022

Project Type


Program or Major


Degree Name

Doctor of Philosophy

First Advisor

Erik B Berda

Second Advisor

John G Tsavalas

Third Advisor

Margaret E Greenslade


The aim of this dissertation is to provide insight into synthetic materials that replicate the function and structure of natural materials. First, a comprehensive overview of the challenges and recent advances in tailored synthetic molecular recognition through molecularly imprinted polymers (MIPs) will be presented. Chapter 2 of this work discusses the synthesis of azlactone-based homopolymers as functional polymers tuned for the detection of opioid molecules. Through the rapid and efficient ring-opening reaction of azlactone pendant chains with primary amines, customized functionalization of the homopolymers with receptor-like moieties was achieved post-polymerization. Chapter 3 explores the use of functionalized diblock copolymers as protein mimics for single-chain nanoparticle (SCNP) collapse. The collapse was successful by use of a newer, one-pot deprotection and coupling Sonogashira-like reaction without copper-catalyst. The polymers and associated nanoparticles were analyzed by size-exclusion chromatography equipped with a multi-angle light scattering (SEC-MALS) detector. Shifts in retention time from polymer to nanoparticle was indicative of change in hydrodynamic volume, suggesting that the polymer was folded into SCNP. Chapter 4 investigates the use of functionalized diblock copolymers with Diels—Alder reaction compatible monomers to form SCNP. Like Chapter 4, shifts in the retention time were observed between polymer and nanoparticle, and SCNP formation discussed.