Master of Science, Miami University, 2024, Chemistry and Biochemistry

Chapter 1 introduces carbodiimide-driven anhydride formation from carboxylic acids, a useful reaction in a variety of non-equilibrium systems. It also introduces established techniques for regulating this reaction. Multiple strategies to control deactivation (anhydride hydrolysis) rates have been reported, but control over activation (anhydride formation) rates is limited. It also explores the role that pyridine already plays within established carbodiimide systems. Chapter 2 explores the reversible reaction of pyridine derivatives with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide methiodide in water to form adducts. These adducts are unreactive with carboxylic acids and thus reduce the anhydride formation rate while prolonging carbodiimide lifetime. The best results are obtained with 4-methoxypyridine. We demonstrate that this strategy can be used to control the formation of transient polymer network hydrogels, in one example increasing the time to reach peak modulus by 86% and the lifetime by 43%. Chapter 3 concludes and summarizes the work completed in Chapters 1-2 and provides future directions and opportunities with the carbodiimide adduct system. The appendix includes supporting information.

Committee: C. Scott Hartley (Advisor); Dominik Konkolewicz (Committee Member); Rock Mancini (Committee Member); David Tierney (Committee Member) Subjects: Chemistry; Organic Chemistry