Palladium Catalyzed Suzuki-Miyaura Synthesis of 2-(4-nitrophenyl)-thiophene and 2-(4-methylphenyl)-thiophene Monomer and Dimer

Abstract

Thiophene dimerization reactions have become of interest in the growing fields of Green and Energy Chemistry, due to the ability of thiophene dimers to store energy in the carbon-carbon dimer bond. Intermittent renewable energy sources, such as solar power, require extensive battery storage capacity in order to provide energy consistently. A proposed solution to the problem of solar energy storage are solar-powered thiophene dimerization reactions that can store the energy in carbon-carbon bonds until released through reaction. Thiophene dimers are ideal for this kind of energy storage, as they have high energy density, are lightweight molecules, and can undergo reversible redox chemistry. Suzuki-Miyaura coupling reactions between an aryl boronic acid and 2-bromothiophene monomer or dimer forms the aryl-thiophene monomer or dimer of interest. For ease of comparison, all aryl compounds studied are para-substituted. Two different thiophene monomers were synthesized. Future studies will be directed at synthesizing a family of thiophene monomers and dimers for study and fabricating solar energy storage devices from these molecules. This will allow for the study of the redox chemistry of energy storage/release from carbon-carbon bonds.