Organic semiconductors have the potential to be used in the manufacture of solution processable thin film transistors (TFTs), and may provide an inexpensive alternative to current silicon technology. One promising family of semiconducting organic molecules is oligothiophenes. The purpose of this research is to synthesize and characterize arene-capped oligothiophenes with alkyl substituents for use as the semiconducting layer in a TFT. Unsubstituted molecules show p-type behavior and a herringbone packing motif. The addition of alkyl substituents will force the molecules into a g-stacking structure in the solid state and change the behavior of the semiconductor. The alkyl substituents will also provide increased solubility, which can provide ease in the characterization and possible spin coating of films. All the molecules synthesized in this study will be characterized by methods that include: nuclear magnetic resonance spectroscopy, UV-VIS spectroscopy, X-ray crystallography, mass spectrometry, and cyclic voltammetry.