The work presented in this thesis describes the design and preparation of asymmetrical, amphiphilic dithienylethenes (DTEs). In general, enhancing the photochromic properties of DTEs is crucial to their application in biocompatible drug delivery systems. The syntheses of DTEs 1–4 were carried out following various devised synthetic routes. Within these synthetic routes, the efficiency of two coupling reactions was found to be important to the overall efficiency of these syntheses. The first reaction involved the regioselective substitution at the 2– and 5–position of thiophene derivatives with aryl- and alkylaryl-substituted boronic acids via Suzuki–Miyaura cross-coupling reactions. In most cases, these substitution reactions were successful in moderate yields. Secondly, lithium-halogen exchange reactions were used to generate the 3-thienyllithium intermediates that were then coupled to mono-substituted perfluorocyclopentene derivatives via a nucleophilic addition–elimination reaction. The efficiency of this coupling reaction was greatly influenced by the nature of substituents at the 2–, 2'–, 4–, 4'– and 5–, 5'–positions of the thiophene ring systems. The synthesis of 1 and 3 and intermediate products for 2 and 4 were successfully prepared. However, the final coupling reaction used to prepare the precursors of 2 and 4 was unsuccessful. It was concluded that the preparation of 2 and 4 would be viable if the scale of these synthetic routes was increased ten fold.