Date of Award

Spring 2026

Language

English

Embargo Period

5-14-2026

Document Type

Master's Thesis

Degree Name

Master of Science (MS)

College/School/Department

Department of Chemistry

Program

Chemistry

First Advisor

Marina Petrukhina

Committee Members

Marina Petrukhina, Evgeny Dikarev

Keywords

Molecular Nanographene, Chemical Reduction, Alkali Metal Intercalation, Corannulene

Subject Categories

Chemistry | Inorganic Chemistry | Organic Chemistry

Abstract

Corannulene is a bowl-shaped π-conjugated fragment of the ball-shaped C60-fullerene that undergoes stepwise multielectron reduction and can accept four electrons to form the aromatic tetraanion, C₂₀H₁₀⁴⁻. Prior literature has established this charge state in donor-solvated alkali-metal assemblies: early solution studies identified the formation of the tetraanion under lithium reduction in THF, and later X-ray diffraction crystallography demonstrated a triple-decker lithium sandwich in which two corannulene tetraanion decks encapsulate five Li⁺ ions. The central objective of this thesis is to determine whether the corannulene tetraanion can instead be isolated as a bulk solvent-free alkali-metal salt containing only corannulene and alkali metal cations, without coordinated donor solvent. Two strategies are investigated. The first approach examines the direct solid-state reduction and intercalation of corannulene with Li, K, Rb, and Cs under oxygen- and moisture-free conditions. To date, these reactions have primarily yielded amorphous materials; however, observable changes in the reaction mixtures indicate that chemical interaction between corannulene and the alkali metals is occurring. The second approach involves reproducing the previously reported THF-solvated corannulene tetraanion complex, followed by removal of the coordinated solvent through reduced pressure/high-temperature THF extraction. This method has yielded a mixed-phase material, which requires further investigation. Since alkali-metal intercalation plays a central role in charge transport, electronic conductivity, and battery-related materials chemistry, solvent-free alkali-metal corannulene tetraanion salts could serve as simplified molecular models for studying metal insertion into curved carbon frameworks, including fullerene fragments, carbon nanotubes, and graphitic electrode materials.

License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.

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