Synthesis of Melanin Polymerization Modifiers
Location
Science Center: Bent Corridor
Document Type
Poster
Start Date
4-28-2023 12:00 PM
End Date
4-28-2023 2:00 PM
Abstract
Synthetic analogs of melanins, the biological pigments, are being explored for numerous applications in materials science. Eumelanin, the black to brown human pigment, is formed through a combination of oxidative polymerization and self-assembly. These modifiers can be used to influence synthetic eumelanin formation and optimize the resulting material for specific applications. Most small molecules tested so far have been commercially available compounds. We are using organic synthesis to generate next-generation modifiers by combining the beneficial features of previously studied modifiers with features of the eumelanin intermediates themselves. The target compounds have features ranging from eumelanin-like oxygenated indole rings to aggregation-promoting positive charges. Each target has an amide bond, and we are exploring some new catalytic amidation reactions in addition to classic reactions used in peptide synthesis. We are testing several potential catalysts including silica gel, tripenylborate, and tetrahydroxydiboron. We are characterizing the reaction products by NMR, GC-MS, and LC-MS. This poster will report on our current efforts toward the synthesis of new modifiers of synthetic eumelanin polymerizations.
Keywords:
Melanin, Synthesis
Recommended Citation
Lee, Jenny; Chvatal, Jo; and Belitsky, Jason, "Synthesis of Melanin Polymerization Modifiers" (2023). Research Symposium. 18.
https://digitalcommons.oberlin.edu/researchsymp/2023/posters/18
Major
Chemistry
Project Mentor(s)
Jason Belitsky, Chemistry and Biochemistry
2023
Synthesis of Melanin Polymerization Modifiers
Science Center: Bent Corridor
Synthetic analogs of melanins, the biological pigments, are being explored for numerous applications in materials science. Eumelanin, the black to brown human pigment, is formed through a combination of oxidative polymerization and self-assembly. These modifiers can be used to influence synthetic eumelanin formation and optimize the resulting material for specific applications. Most small molecules tested so far have been commercially available compounds. We are using organic synthesis to generate next-generation modifiers by combining the beneficial features of previously studied modifiers with features of the eumelanin intermediates themselves. The target compounds have features ranging from eumelanin-like oxygenated indole rings to aggregation-promoting positive charges. Each target has an amide bond, and we are exploring some new catalytic amidation reactions in addition to classic reactions used in peptide synthesis. We are testing several potential catalysts including silica gel, tripenylborate, and tetrahydroxydiboron. We are characterizing the reaction products by NMR, GC-MS, and LC-MS. This poster will report on our current efforts toward the synthesis of new modifiers of synthetic eumelanin polymerizations.
