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Cited by 591melanin and skin pigmentationConducting polymers and applicationsSynthesis and Properties of Aromatic Compounds

Chemical and Structural Diversity in Eumelanins: Unexplored Bio‐Optoelectronic Materials

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d'Ischia, Marco, Napolitano, Alessandra, Pezzella, Alessandro, Meredith, Paul, Sarna, Tadeusz·2009·Angewandte Chemie International Edition
DOI 10.1002/anie.200803786PMC PMC2799031
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Abstract

A black whole: The black insoluble biopolymer eumelanin is prepared through the oxidative polymerization of 5,6‐dihydroxyindoles (see scheme). It has a largely unknown heterogeneous structure and unique optoelectronic properties. Current structural models are presented and possible applications are discussed.magnified image Eumelanins, the characteristic black, insoluble, and heterogeneous biopolymers of human skin, hair, and eyes, have intrigued and challenged generations of chemists, physicists, and biologists because of their unique structural and optoelectronic properties. Recently, the methods of organic chemistry have been combined with advanced spectroscopic and imaging techniques, theoretical calculations, and methods of condensed‐matter physics to gradually force these materials to reveal their secrets. Herein we review the latest advances in the field with a view to showing how the emerging knowledge is not only helping to explain eumelanin functionality, but may also be translated into effective strategies for exploiting their properties to create a new class of biologically inspired high‐tech materials.

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  • The first model exhibits a "covalent bonding" polymerization fashion where DA is polymerized via 5,6-dihydroxyindole monomers following further oxidization and subsequent intermolecular cross-linking of PDA.

    “The first model exhibits a “covalent bonding” polymerization fashion where DA is polymerized via 5,6-dihydroxyindole monomers following further oxidization and subsequent intermolecular cross-linking of PDA [29, 40–44].”

    From Polydopamine-Assisted Surface Modification for Bone Biosubstitutes (2016) · cites this paper as [42]

    The Introduction (page not provided) describes oxidative polymerization of 5,6-dihydroxyindole precursors into eumelanin. Section 2 (page not provided) describes oxidation and interring bonding of those indole units. The paper does not establish the claimed pathway specifically for dopamine (DA) polymerization into polydopamine (PDA). (LLM, conf=0.87)

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Authors
d'Ischia, M., Napolitano, A., Pezzella, A., Meredith, P., & Sarna, T.
Affiliations
  • University of Naples Federico II (IT)
  • The University of Queensland (AU)
  • Jagiellonian University (PL)
ORCID
Venue
Angewandte Chemie International Edition
Publisher
Wiley
Published
2009-05-12
Volume
48
Issue
22
Pages
3914-3921
ISSN
  • 1433-7851 (ISSN-L)
  • 1521-3773
DOI
10.1002/anie.200803786
PMC
PMC2799031
OpenAlex
W2001038139
Cited by
591
References
2
Citations by year
2026: 23 · 2025: 23 · 2024: 23 · 2023: 29 · 2022: 39 · 2021: 42 · 2020: 36 · 2019: 33 · 2018: 49 · 2017: 38 · 2016: 43 · 2015: 41 · 2014: 45 · 2013: 46 · 2012: 29
FWCI
2.05
Type
journal article
Language
en
Open access
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations
  • Angewandte Chemie International Edition (publishedVersion)
  • PubMed (publishedVersion)
  • PubMed Central (acceptedVersion)
  • Jagiellonian University Repository (Jagiellonian University) (submittedVersion, other-oa)
  • Scuola Normale Superiore di Pisa (submittedVersion)
Funders
National Eye Institute (R01EY013722)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › melanin and skin pigmentation
  • Physical Sciences › Materials Science › Polymers and Plastics › Conducting polymers and applications
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
Keywords
eumelanin, 5,6-dihydroxyindole, oxidative polymerization, biopolymer structure, optoelectronic properties, black pigment, biomimetic materials, skin pigmentation
MeSH terms
Humans, Light, Melanins, Models, Chemical, Oxidation-Reduction, Semiconductors, Molecular Structure

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