Date of Award

Spring 2026

Degree Type

Thesis

Department

Chemistry and Biochemistry

Director of Thesis

Dr. Linda Shimizu

Second Reader

Vaibhavi Samant

Abstract

Macrocycles are large, cyclic molecules with central cavities that can encapsulate other molecules and that have uses in supramolecular chemistry. The Shimizu group has previously synthesized Macrocycle 1, a phenylethynylene bis-urea macrocycle that crystallizes in a columnar form, enabling its utility as a host in host-guest systems. Reactions within these systems can be used to modify stereospecificity, kinetics, and other physical properties. Previously, photodimerization reactions between coumarins and chromones have been studied in systems of Macrocycle 1, resulting in the improved specificity of photodimerization products. Herein, we apply a dynamic covalent chemistry (DCC) strategy to synthesize Macrocycle 1 and its brominated derivative Macrocycle 2, improving the yield of the cyclization reaction of macrocycle 1 and 2 from 10% to 68% and 29%, respectively. We are screening crystallization conditions to obtain large crystals of 1 and 2 for structure elucidation by single-crystal X-ray diffraction. Additionally, co-crystal formation is being screened using a range of molar-ratio mixtures of Macrocycles 1 and 2. This thesis will contribute to the design of functional materials for the synthesis of useful photoproducts that are challenging to synthesize.

First Page

1

Last Page

58

Rights

© 2026, Paras Srivastava

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