Publication Date


Document Type


First Advisor

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

Degree Name

Ph.D. (Doctor of Philosophy)

Legacy Department

Department of Chemistry and Biochemistry


Organic chemistry


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.


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


ix, 344 pages




Northern Illinois University

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