Abstract

Our group has demonstrated the feasibility of utilizing phenazine-1,6-dicarboxamides as redox-responsive molecular switches: changes in the oxidation state of the phenazine core forces the secondary amide arms to rotate between the doubly folded form when oxidized and the unfolded form when reduced to its dihydrophenazine form. To construct phenazine-based oligomers, we have developed dibenzofuran linkers that can easily be decorated with different solubilizing groups and incorporated into the foldamer backbone. In our initial attempts, we used xanthene linkers. However, problems with limited solubility and preference for cyclization prompted us to consider an alternative cisoid linker with a wider bite angle. Structurally similar to xanthene, the geometry of dibenzofuran addressed all the drawbacks associated with the xanthene linker and its synthesis allowed us to easily introduce side chains to enhance its solubility. The synthesis, characterization, and redox studies of these dibenzofuran and phenazine-based oligomers have been described.

Committee Chair

Vladimir Birman

Degree

Doctor of Philosophy (PhD)

Author's Department

Chemistry

Author's School

Graduate School of Arts and Sciences

Document Type

Dissertation

Date of Award

9-1-2023

Language

English (en)

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