Supramolecular Chemistry focuses on the intramolecular interactions between molecules, such as hydrogen bonding and anion binding. Dipyrrinones are found in many biological molecules, such as Bilirubin, Biliverdin, and Urobilin, and are well known to be avid participants in hydrogen bonding.  They have been shown to form dipyrrinone-dipyrrinone dimers via a network of four intermolecular hydrogen bonds.  In this research, a series of dipyrrinones with amide functionality in the 7-position have been prepared to improve solubility and provide an opportunity to build larger supramolecular systems using the dipyrrinone hydrogen bonding as the building blocks.  The synthesis and characterization of these new dipyrrinone systems will be presented. The synthetic route for the amide derivative of the mono-dipyrrinones has been established and the same route is being applied to synthesize the bis-dipyrrinones of the amides, while the synthetic route to the urea derivatives of the mono-dipyrrinones is being completed.

Synthesis and characterization of dipyrrinones as supramolecular building blocks

251st National Meeting (2016)

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