Eumelanin, the brown-to-black pigment present in mammals, is formed through the oxidative polymerization of dihydroxyindoles to form a heterogeneous mixture of oligomers. This complex natural pigment, along with numerous bio-inspired synthetic derivatives, have been of considerable interest in materials chemistry, finding applications in areas as diverse as modifiable surface coatings, organic electronics and metal remediation. Despite its broad and growing applications, the discrete molecules and supramolecular assembly of the oligomers that constitute eumelanin are still poorly understood. In order to explore the composition and unique physical properties of eumelanin, the Belitsky group has worked to develop a modular, metal-mediated synthetic approach to systematically create a library of biologically relevant oligomers, varying in regioconnectivity and monomer length. Specifically, commercially available 5,6-dimethoxyindole (DMI) and ethyl-5,6-dimethoxyindole-2-carboxylate (DMICE) have been functionalized via regioselective halogenation and iridium-catalyzed borylation at the 2-,3-,4- and 7-positions of the indole. Using a Suzuki coupling, the functionalized 5,6-dimethoxyindoles were assembled into dimers, trimers and tetramers in good yields.

Metal-mediated modular synthesis of eumelanin-inspired 5,6-dimethoxyindole oligomers

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

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