Date of Award
1-1-2022
Document Type
Dissertation
Degree Name
Ph.D. in Chemistry
Department
Chemistry and Biochemistry
First Advisor
Davita Watkins
Second Advisor
Jared Delcamp
Third Advisor
James Cizdziel
Relational Format
dissertation/thesis
Abstract
Halogen bonding (XBing) is a type of non-covalent interaction between covalently bound halogen atoms (XB donor), and Lewis bases (XB acceptor). In recent years, it has become a remarkable and adaptable tool to produce interesting molecular architectures and functionalities in organic-based materials. Such applications include liquid crystals, nonlinear optics, photovoltaics, and multicolor displays in the solid phase. Due to this variety of applications, XBing has become an exciting area of study in supramolecular chemistry. Herein are presented synthetic routes and characterization of self-assembling XBing molecules and their resulting materials. First, four different heterocyclic oligomers containing pyrazine, thiophene, and furan have been synthesized as XB acceptors. Their solution and solid-phase properties were studied via spectroscopic, electrochemical, and single-crystal (X-ray diffraction) XRD analysis to highlight the impact of molecular packing on material properties. Second, newly synthesized pyrimidine-based self-assembling XB building blocks were introduced, and their XBing nature in the solution-state was studied. Finally, a Schiff-based pyridine-capped halogen bonding acceptor molecule was synthesized. Its halogen bonding nature was investigated with two different halogen bonding donors in a solution state using NMR and UV-Vis spectroscopy. The findings of this study emphasize the importance of using prudent design criteria for materials to induce favorable optical and photophysical properties and achieve advanced materials.
Recommended Citation
Karunathilaka, Dilan Chinthaka, "Halogen Bond Driven Supramolecular Materials" (2022). Electronic Theses and Dissertations. 2237.
https://egrove.olemiss.edu/etd/2237