| In the quest to develop low cost energy production, utilization of solar energy to generate electrical energy has gained wide attention in recent years. Artificial photosynthetic systems, mimicking natural photosynthesis, are emerging as a promising approach for efficient photoinduced electron transfer and, consequently, a powerful technique to afford low cost electrical energy. Hydrogen-bonded supramolecular systems hold great promise in this application due to the involvement of H-bonds in electronic communication. Therefore, such a system possessing multi-point, hydrogen-bonded groups have the potential to enhance the photo conversion efficiency significantly.;Among the small organic molecule n-type semiconductors, perylene tetracarboxylic diimides (PDIs) and perylene tetracarboxylic dianhydrides (PTCDs) possess great potential due to the combination of a variety of desirable characteristics such as excellent thermal and photostability, high molar absorptivities and good electron accepting properties. Because of these attractive properties, PDIs are being heavily researched as materials in the burgeoning field of organic electronics such as organic photovoltaic, n-channel materials, organic thin film transistors, etc. PDIs have great potential due to their ability to form self-assembled complex architectures via their high propensity for pi-pi stacking which can be coupled with other intermolecular interactions, such as hydrogen bonding, to form ordered functional systems. This dissertation focuses on the convenient synthesis and separation of 1,6- and 1,7-regioisomers of PDIs and PTCDs, the comparison of their anonymous properties, the effect of multi-point hydrogen bonding motifs on the self-assembly of PDIs, and the electron transport properties of novel derivatives of PTCDs. |
