Author

Solmaz Asadi

Date of Award

December 2024

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Qianli R. Chu

Abstract

The present work examines the photoreactivity of 4-hydroxy-2(5H)-furanone and 2-pyridone un-der varying conditions, with the aim of investigating how solvent and wavelength can influence their photochemical reactivity. In the first chapter, the photoreactivity of 4-hydroxy-2(5H)-furanone in its crystalline state was observed to undergo a [2+2] photocycloaddition reaction when exposed to UV-C light and led to a new cyclobutane containing dimer (CB-SA-1). More impressively, CB-SA-1 was determined to be stable at room temperature for two years. This method was solvent-free and catalyst-free offering an environmentally friendly method for synthesizing furanone deriva-tives. Further, in order to study the photoreactivity of 4-hydroxy-2(5H)-furanone in solution, with acetone as a solvent and under UV-A light exposure, a new compound 3,3'-(propane-2,2-diyl)bis(4-hydroxyfuran-2(5H)-one) (BHF) was observed. This method is environmentally friend-ly, generating only water as a byproduct. It also features straightforward purification processes and produces minimal waste. In the second chapter it was found that 2-pyridone (in solid form) is inert upon exposure to various UV lights and no reaction takes place. However, in solution, it under-went [4+4] photocycloaddition under UV-C light with a good yield of 90%. These results show the impact of substrate state, the nature of the solvent used, and the type of UV light on the yield of photoreaction products. These methods provide the opportunity for the synthesis of organic com-pounds through green pathways that might find use in a variety of fields, such as medicine, agricul-ture, and engineering, among many others.

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