Date of Award

Spring 5-1-2015

Document Type

Honors Project

Degree Name

Bachelor of Science

Department

Chemistry

First Advisor

Crowder, K. Nicole

Second Advisor

Giancarlo, Leanna C.

Major or Concentration

Chemistry (ACS Certified)

Abstract

Carbon dioxide, an abundant waste gas, can be electrochemically reduced with the aid of a catalyst. By modifying a conductive surface, such as copper, with a tailored catalytic complex, the surface simultaneously functions as a working electrode for this electrocatalytic reduction and theoretically facilitates selective reduction to multi-carbon species. The necessary modification requires a bifunctional ligand, capable of both transition metal catalyst coordination and surface tethering; such molecules have been synthesized via multiple routes from the same precursor bipyridine molecule. Commercially available 4,4'-dimethyl-2,2'-bipyridine can be alkylated using a dibrominated alkane substrate, functionalizing the molecule for subsequent synthetic modification. Optimization of chain length has been pursued; both 4,4'-di(10-bromodecyl)-2,2'-bipyridine and 4,4'-di(6-bromohexyl)-2,2'-bipyridine have been isolated and employed in further syntheses. Alternatively, the methyl substituents of the same bipyridine starting material may be radically brominated, allowing for a more direct functionalization. Following installation of a phosphonate at the previously brominated terminus, the bipyridine derivative is then able to be converted to a phosphonic acid, which permits robust covalent binding to a copper oxide surface. These routes allow for the construction of the modified electrodes necessary to reduce carbon dioxide to synthetically useful species. Synthesis and characterization of isolated bipyridine-containing precursors and modified conductive surfaces are presented in an attempt to develop a consistent route to effective, efficient electrodes.

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