Date of Award

2025

Degree Name

Chemistry

College

College of Science

Type of Degree

M.S.

Document Type

Thesis

First Advisor

Dr. Michael Castellani

Second Advisor

Dr. John Markiewicz

Third Advisor

Dr. Shin Moteki

Abstract

The work described in this thesis has generated new oligoviologen structures designed to facilitate the formation of supermolecules that incorporate photoactive and redox-active groups. These viologens have several potential uses; for example, the 4+ oligoviologen (viologen 5) exhibits solvatochromic properties in various polar protic and polar aprotic solvents, indicating suitability for use as a solvatochromic dye. The syntheses of bis(4,4’-bipyridine)ortho-xylene, bis(4,4’-bipyridine)meta-xylene, and bis(4,4’-bipyridine)para-xylene were demonstrated through 1H NMR characterization and confirmed through literature. Bis(4,4’-bipyridine)ortho-xylene, bis(4,4’-bipyridine)meta-xylene, and bis(4,4’-bipyridine)para-xylene were produced in 68%, 72%, and 54% yields, respectively. 4,4’-Bipyridine-1-[4-(bromomethyl)phenylmethyl]-1’- propanol, 4,4’-bipyridine-1-[3-(bromomethyl)phenylmethyl]-1’-propanol, 4,4’-bipyridine-1-[2- (bromomethyl)phenylmethyl]-1’-propanol, 4+ oligoviologen isomers, 6+ oligoviologen isomers, and 8+ oligoviologen isomers were new molecules. The syntheses of 4,4’-bipyridine-1-[4- (bromomethyl)phenylmethyl]-1’-propanol, 4,4’-bipyridine-1-[3-(bromomethyl)phenylmethyl]- 1’-propanol, and 4,4’-bipyridine-1-[2-(bromomethyl)phenylmethyl]-1’-propanol were confirmed by comparison to literature reported comparable compounds with similar 1H NMR peaks. 4,4’- Bipyridine-1-[2-(bromomethyl)phenylmethyl]-1’-propanol, was produced in a 46% yield. 4,4’- bipyridine-1-[3-(bromomethyl)phenylmethyl]-1’-propanol, was produced in a 40% yield. 4,4’- bipyridine-1-[4-(bromomethyl)phenylmethyl]-1’-propanol was produced in a 42% yield. The 4+ oligoviologen ortho isomer yielded 1.02 g containing impurities, such as starting reagents. The 6+ oligoviologen para-para isomer yielded 0.38 g but contained impurities, such as starting reagents. The OOO 8+ oligoviologen isomer was synthesized, and its yield was determined to be 45% based on integrations from the 1H NMR spectrum peaks. The product was obtained in 45% yield due to impurities present in the sample.

Subject(s)

Chemistry.

Chemistry, Organic.

Molecules.

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