Melanins and their corresponding synthetic analogues have found numerous and varied applications in materials chemistry, from adhesives to organic semiconductors. Despite the recent surge in interest in these biopolymers, the supramolecular assembly of the oligomeric indole species remains poorly understood. To explore these non-covalent interactions, modular synthetic schemes are being developed to systematically create a library of oligomers from commercially available 5,6-dimethoxyindole (DMI) and ethyl-5,6-dimethoxyindole-2-caboxylate (DMICE). The 5,6-dimethoxyindole starting materials were functionalized through a combination of regioselective halogenation, iridium-catalyzed borylation and Suzuki coupling chemistry. Specifically, DMICE has been monofunctionalized with aryl and heteroaryl substituents at the 3-position and difunctionalized at the 3,7- and 4,7-positions to create a series of novel 5,6-dimethoxyindole compounds, including biologically relevant indole dimers and trimers.

Developing a modular synthesis of Eumelanin oligomers

254th National Meeting (2017)

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