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Issue 44, 2018
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Polydopamine and eumelanin models in various oxidation states

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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.

Graphical abstract: Polydopamine and eumelanin models in various oxidation states

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Publication details

The article was received on 07 Aug 2018, accepted on 08 Oct 2018 and first published on 09 Oct 2018


Article type: Paper
DOI: 10.1039/C8CP05037F
Citation: Phys. Chem. Chem. Phys., 2018,20, 28135-28143
  • Open access: Creative Commons BY-NC license
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    Polydopamine and eumelanin models in various oxidation states

    C. Chen and M. J. Buehler, Phys. Chem. Chem. Phys., 2018, 20, 28135
    DOI: 10.1039/C8CP05037F

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