2+ 2 cycloaddition reactions provide a means by which solids can react in the presence of light without any solvent. The reactants are oriented by metal-organic complexes that act as templates. These reactions are very useful in forming products that could otherwise not be formed in the liquid phase and enables stereospecific control of the products. Of particular interest to us is the synthesis of the organic compounds used in these metal-organic co-crystals. Acquisition of these organic molecules is an often overlooked and expensive process as many are not commercially available. New novel syntheses of these precursor molecules from readily-accessible starting materials provide a synthesis problem approachable at the undergraduate level.
We attempted to devise simple synthetic routes for three organic molecules with the ultimate goal of performing solid-state photochemical reactions. Development of multistep synthesis procedures required optimization of the reaction procedure as well as purification and identification of several intermediates. Upon successfully producing one of the templates, 4-4’-bispyridylethylene-resorcinol, an attempt at performing a photochemical transformation was made. From this reaction, a small but identifiable amount of the target compound was created, revealing that the methods used were successful, as well as providing a clear direction for further research.
Adam Jones, ’13
Grays Lake, IL
Samantha de Gannes, ’13
Diego Martin, Trinidad
Majors: Biochemistry and Molecular Biology, Spanish
Sponsor: Charles Liberko