Project Director

Dungey, Keenan

Department Examiner

Pienkos, Jared; Rybolt, Thomas R.

Department

Dept. of Chemistry and Physics

Publisher

University of Tennessee at Chattanooga

Place of Publication

Chattanooga (Tenn.)

Abstract

Two-dimensional crystals have unique properties, giving them the potential to develop practical items such as electronics, biomedicine, and sensors. Our goal is to use chemical principles to synthesize molecules that spontaneously form 2D crystals with designed patterns and properties. For this, we will exploit directional, non-covalent interactions to determine what pattern will form in 2D. In this project halogen-bonding will be utilized: halogen-bonding is the interaction between the electrophilic region of a halogen and a nucleophilic region of a Lewis base. We are functionalizing anthracenes with iodine and nitrogen to form halogen bonds that enable the molecules to pack more uniformly. The flat, stable, conjugated composition of anthracenes makes them good candidates for 2D molecular crystals. Our hypothesis is that halogen-bonded anthracenes will have an offset row tiling pattern in 2D.

Acknowledgments

I would like to thank everyone who has assisted me with this thesis and research: - Dr. Keenan Dungey, for helping me write this thesis and for assisting me with STM characterization. - Dr. Jared Pienkos, for helping write this thesis and for assisting me with synthesis and NMR characterization. - Dr. Tom Rybolt, for providing valuable advice for this research. - The University of Tennessee Department of Chemistry and Physics, for providing travel funding and for supporting this thesis and research. - Dr. Colin McMillen from Clemson University, for providing crystal structures and data - Mr. Richard X. Zhang, for providing the funding for this research through the Tom Rybolt and Richard X. Zhang Endowed Undergraduate Research in Chemistry Scholarship and for giving me an opportunity to spend a summer on this project. - Marisa James, for all the synthesis, recrystallization, and NMR characterization she did

Degree

B. S.; An honors thesis submitted to the faculty of the University of Tennessee at Chattanooga in partial fulfillment of the requirements of the degree of Bachelor of Science.

Date

5-2024

Subject

Anthracene; Halogen compounds; Molecular crystals

Keyword

molecular crystals; 9,10-bis(iodoethynyl); anthracene; halogen-bonding; pi-stacking

Discipline

Materials Chemistry

Document Type

Theses

Extent

iv, 37 leaves

DCMI Type

Text

Language

English

Rights

http://rightsstatements.org/vocab/InC/1.0/

License

http://creativecommons.org/licenses/by/4.0/

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