2024 Theses Doctoral

Applications of Charged Aromatic Species in Electronics

Prindle, Claudia

Charged organic species are ubiquitous throughout organic chemistry. They are ideal ascomponents in organic electronics, and are common as transition states or intermediates in many organic transformations. This dissertation details the investigation of the effect of external electric fields on reactions with charged transition states, as well as the incorporation of triarylmethylium and triangulenium cations as components in single-molecule and organic electronics.

Chapter 1 provides an introduction to the scanning tunneling microscope break junction (STM-BJ) technique, which is used as a tool to assess the effect of external electric fields on reaction rate and the performance of single-molecule devices. In this chapter, the different design criteria for molecules used in both single-molecule and optoelectronic devices are discussed.

Chapter 2 evaluates the effect of electric fields on two classes of reactions with charged transition states – the Menshutkin reaction and the Chapman rearrangement. Chapter 3 describes triarylmethylium and triangulenium dyes as single-molecule devices, and how their conductance can be tuned through different pendant substituents via Fano resonances. Chapter 4 details an ongoing project that incorporates triangulenium cores to yield a modular donor-acceptor system that shows tunable quenching of emission.

Finally, Chapter 5 chronicles the progress of our TikTok account called @IvyLeagueScience and outlines the success criteria for using short-form videos as a way of conducting scientific outreach.