Anisotropic Synthetic Allomelanin Materials via Solid-State Polymerization of Self-Assembled 1,8-Dihydroxynaphthalene Dimers

Xuhao Zhou, Xinyi Gong, Wei Cao, Christopher J. Forman, Julia Oktawiec, Liliana D'Alba, Hao Sun, Matthew P. Thompson, Ziying Hu, Utkarsh Kapoor, Naneki C. McCallum, Christos D. Malliakas, Omar K. Farha, Arthi Jayaraman, Matthew D. Shawkey, Nathan C. Gianneschi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Melanosomes in nature have diverse morphologies, including spheres, rods, and platelets. By contrast, shapes of synthetic melanins have been almost entirely limited to spherical nanoparticles with few exceptions produced by complex templated synthetic methods. Here, we report a non-templated method to access synthetic melanins with a variety of architectures including spheres, sheets, and platelets. Three 1,8-dihydroxynaphthalene dimers (4-4′, 2-4′ and 2-2′) were used as self-assembling synthons. These dimers pack to form well-defined structures of varying morphologies depending on the isomer. Specifically, distinctive ellipsoidal platelets can be obtained using 4-4′ dimers. Solid-state polymerization of the preorganized dimers generates polymeric synthetic melanins while maintaining the initial particle morphologies. This work provides a new route to anisotropic synthetic melanins, where the building blocks are preorganized into specific shapes, followed by solid-state polymerization.

Original languageEnglish (US)
Pages (from-to)17464-17471
Number of pages8
JournalAngewandte Chemie - International Edition
Volume60
Issue number32
DOIs
StatePublished - Aug 2 2021

Keywords

  • DHN melanin
  • allomelanin
  • anisotropy
  • melanin
  • solid-state polymerization

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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