Polydopamine and eumelanin models in various oxidation states
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c8cp05037f.pdf
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2.91 MB
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Author(s)
Chen, Chun-Teh
Buehler, Markus J
Date Issued
October 2018
Journal
Physical Chemistry Chemical Physics
Publisher
Royal Society of Chemistry (RSC)
Citation
Chen, Chun-Teh and Markus J. Buehler. “Polydopamine and Eumelanin Models in Various Oxidation States.” Physical Chemistry Chemical Physics 20, 44 (2018): 28135–28143
Version
Final published version
Abstract
We report a comprehensive ab initio structural investigation of more than 43 000 probable molecular structures of polydopamine (PDA) and eumelanin in various oxidation states. With the aid of a computational approach including a brute-force algorithmic generation of chemical isomers and density functional theory, all probable oxidized 5,6-dihydroxyindole (DHI) oligomers, ranging from dimers to tetramers, have been systematically generated and evaluated. We identify a set of the most stable molecular structures of PDA and eumelanin which represent the chemically diverse nature of these materials. Results show that more planar molecular structures have a tendency to be more stable. We also observe that, in some cases, forming cyclic molecular structures could reduce the energy of a DHI tetramer and make it more stable. This finding supports the hypothesis that cyclic molecules could exist in eumelanin-like materials. Additionally, the cyclic molecular models proposed in this work are energetically more favorable than the popular porphyrin-like models in this field.
MIT Department
Massachusetts Institute of Technology. Department of Civil and Environmental Engineering
Terms of Use
Creative Commons Attribution-NonCommercial 3.0 Unported
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DOI of Published Version
https://doi.org/10.1039/c8cp05037f
