Melanins are a class of naturally occurring pigmentary macromolecules found in mammals. These compounds have a high degree of conjugation rendering them a powerful radiation absorber with broadband photon absorption spectrum that extends from the ultraviolet into the infrared region. The black-brown variety of melanin is known as eumelanin and is thought to be a heterogeneous network produced by oxidative polymerization of the two monomers, 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid. Groundbreaking work by McGinness and Proctor on electrical switching established that eumelanins were organic semiconductors. Currently, we have synthesized a eumelanin-inspired indole core, methyl 4,7-dibromo-5,6-dimethoxy-<i>N</i>-methyl-<i>1H</i>-indole-2-carboxylate from the plant extract, vanillin, which can serve as new building block for organic semiconductors. The design, synthesis, and characterization of eumelanin-inspired conjugated polymers from this indole core will be presented.

Design and synthesis of eumelanin-inspired polymers derived from vanillin

249th National Meeting (2015)

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