Covalent organic frameworks are a burgeoning area of research that seeks to create compounds that exhibit flexibility and utility. These compounds are ideal for mass transport, as they are chemically stable while providing adjustable cylindrical pore size depending upon the linking groups. Porphyrins have been shown to be effective as one of the linking groups in these frameworks, due to the relative ease of manufacture in comparison to the amounts of conjugation and solar activity they provide. However, there has not been a pathway identified yet that allows for a β-substituted porphyrin to be placed within a framework, and therefore these compounds lack synthetic control. To address this issue, my research is focused around synthesizing and characterizing an important intermediate to creating these compounds: tetrabrominated (<i>p</i>-amino)tetraphenylporphyrin, as the bromination of the porphyrin allows for coupling reactions to further enhance the structure. The initial findings show that working directly from the amino porphyrin leads to a lack of selectivity during bromination, however bromination of the precursor (<i>p</i>-nitro)tetraphenylporphyrin compound shows strong indication of tetrabromination by UV, and current research is aimed at finding a reduction method that does not debrominate the porphyrin. My research shows that porphyrin-based covalent organic frameworks may have the potential to be specialized by bromination of the deactivated nitro porphyrin.

Porphyrin-based covalent organic frameworks: Synthesizing β-substituted intermediate linker porphyrins

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.