Document Type
Honors Thesis
Degree Name
Bachelor of Science
Date of Award
Spring 4-15-2026
Abstract
Once widely used for its vivid presence in an array of industrial dyes, perylene-3, 4, 9, 10-tetracarboxylic dianhydride (PTCDA) is a known precursor for perylene diimides (PDIs). These compounds are an alternative for sustainable energy within organic solar cells (OSCs) and for improving organic light emitting diodes (OLEDs). PDIs are a great candidate for organic semiconductor applications because of their overall flexibility and low manufacturing cost as an organic photovoltaic. Its extended π-conjugation results in a planar structure promoting strong π- π intermolecular stacking, giving aggregated PDIs high electron mobility, allowing a flow of electrons to move through these stacked molecules, and high photochemical stability, a property allowing the compounds to endure high levels of radiation. However, their extended planar structure leads to poor solubility in common organic solvents, limiting their processability and potential for large scale operations.
In this study, PTCDA was functionalized at its anhydride sites with a series of molecular group substituents to produce five PDI variations, denoted A-E. These modifications were designed to improve the solubility characteristics while also preserving the molecule’s ability to aggregate, an important feature for efficient charge mobility. As PDIs stack, their π-orbitals overlap enabling stronger electron delocalization, improving their conductivity and light-emitting properties.
The synthesized derivatives were characterized using proton nuclear magnetic resonance spectroscopy (1H-NMR), mass spectrometry, and fourier-transform infrared (FT-IR) spectroscopy to confirm structural identity and successful functionalization. Further analysis included qualitative solubility testing across an array of organic solvents, UV-Vis spectroscopy to evaluate absorption behavior, and polarized microscopy to assess aggregation tendencies. Together, these methods provide valuable insight into how specific functional groups influence 3 the solubility, aggregation and optical properties, providing a guide to future designs for the optimization of PDIs for organic electronic applications.
Advisor
Stephen Starnes
Recommended Citation
Salinas, Erica, "Exploring the Synthesis, Characterization, and Aggregation Properties of Perylene Diimide Derivatives" (2026). Honors Theses. 292.
https://lair.etamu.edu/honorstheses/292
