Photochromic compounds are of interest due to their ability to undergo reversible color-changing reactions in the presence of UV light.  This type of reaction allows photochromic compounds to be utilized in optical memories and switches. The goal of this project was to synthesize an aromatic compound with photochromic properties deriving from its ability to perform a reversible ring closure reaction (seen below). 

            A variety of methods were used to determine the most effective synthetic approach for the molecule above.  The applicability of the synthetic pathways followed was enhanced by examining a variety of compounds, including molecules with triple bonds, and with different steric hindrances. The reaction yields in the presence of multiple sites of reactivity were also tested.  The result of this exploration determined that the most logical approach to the desired molecule is a reaction sequence involving the Sonogashira reaction and Kumada coupling.