Date Available


Year of Publication


Degree Name

Doctor of Philosophy (PhD)

Document Type

Doctoral Dissertation


Arts and Sciences



First Advisor

Dr. John E. Anthony


Small-molecule organic materials are of increasing interest for electronic and photonic devices due to their solution processability and tunability, allowing devices to be fabricated at low temperature on flexible substrates and offering utility in specialized applications. This tunability is the result of functionalization through careful synthetic strategy to influence both material properties and solid-state arrangement, both crucial variables in device applications. Functionalization of a core molecule with various substituents allows the fine-tuning of optical and electronic properties, and functionalization with solubilizing groups allows some degree of control over the solid- state order, or crystal packing. These combinations of core chromophores with varying substituents are systematically evaluated to develop structure-function relationships that can be applied to numerous applications. This is the basis of Chapter 2, which focuses on identifying trends between physical structure and resulting optical and electronic properties in heteroacenes.

In Chapter 3, the chromophores of Chapter 2 are further functionalized with substituents that allow them to work in tandem with inorganic materials for a hybrid singlet fission-triplet harvesting photovoltaic system. Chapter 4 further explores these key chromophores with still other substituents, here for isolated triplet pair generation and eventual quantum computing applications. Finally, Chapter 5 explores a relatively understudied class of formally antiaromatic compounds, the octadehydro[12]annulenes, demonstrating a unique effort at crystal engineering these molecules using similar strategies as in Chapter 2. A comprehensive overview of the physical, optical, and electronic properties is offered, providing a robust basis for future work.

Digital Object Identifier (DOI)

Funding Information

This research was supported by the National Science Foundation (CHE-1609974) from 2017 - 2021.