Publication Date

2017

Document Type

Dissertation/Thesis

First Advisor

Adler, Marc Jordan, 1981-||Horn, James R.

Degree Name

Ph.D. (Doctor of Philosophy)

Department

Department of Chemistry and Biochemistry

LCSH

Organic chemistry

Abstract

o-Hydroxychalcone and its flavanone isomer undergo facile and complete interconversion in response to a change in pH. These characteristics make the o-hydroxychalcone scaffold an appealing target for use as a molecular switch. The addition of a single methoxy substituent to one of the core phenyl rings was enough to show a measurable deviation in the pH at which there is a 1:1 ratio of isomers, or midpoint pH. The discovery that structural modifications can control the switching behavior led to the synthesis of a library of chalcones containing multiple substituents and variable aromatic rings. It was shown that each analogue was able to maintain its switching functionality and that each modification had a unique and additive effect on the midpoint pH. Through the use of structural modifications, the midpoint pH of the parent compound was changed from a single value of 11.46 to a range that spans from 9.15 to 13.20. Foundational work was also done to assess the viability of the scaffold for use as a beta-turn mimetic to better study reversible beta-sheet formation.

Comments

Advisors: Marc J. Adler; James R. Horn.||Committee members: Timothy Hagen; Douglas Klumpp; Laurence Lurio.||Includes bibliographical references.||Includes illustrations.

Extent

ix, 344 pages

Language

eng

Publisher

Northern Illinois University

Rights Statement

In Copyright

Rights Statement 2

NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.

Media Type

Text

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