Cited by 62Synthesis and Properties of Aromatic CompoundsSynthesis of Indole Derivativesmelanin and skin pigmentation

5,6‐Dihydroxyindole Chemistry: Unexplored Opportunities Beyond Eumelanin

d'Ischia, Marco, Napolitano, Alessandra, Pezzella, Alessandro·2011·European Journal of Organic Chemistry

Abstract

5,6‐Dihydroxyindoles, the key building blocks of eumelanin biopolymers, hold promise as versatile molecular systems for the design and development of new functional aromatic scaffolds, biomimetic polymers, and nanomaterials with tailored optical and electronic properties. During the past decade, research into the photophysics, synthesis, π electron manipulation, and reaction behavior of 5,6‐dihydroxyindoles has expanded beyond the traditional boundaries of biology and medicine to involve physicists, organic chemists, and materials scientists. This review presents the latest advances in 5,6‐dihydroxyindole chemistry from a new perspective. Touching only upon themes at the periphery of eumelanin research, it seeks rather to throw light on the chemical and photophysical features of this peculiar π electron system as an unexplored conceptual and practical platform on which synthetic creativity and rational design might generate a range of chemically diverse molecular scaffolds.

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Crossref · 10.1002/ejoc.201100796

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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].”

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Authors
d'Ischia, M., Napolitano, A., & Pezzella, A.
Affiliations
University of Naples Federico II (IT)
Venue
European Journal of Organic Chemistry
Publisher
Wiley
Published
2011-09-02
Volume
2011
Issue
28
Pages
5501-5516
ISSN
  • 1099-0690 (ISSN-L)
  • 1434-193X
OpenAlex
W2141923410
Cited by
62
References
83
Citations by year
2026: 3 · 2025: 2 · 2024: 4 · 2023: 3 · 2022: 5 · 2021: 3 · 2020: 2 · 2019: 8 · 2018: 2 · 2017: 5 · 2016: 11 · 2015: 5 · 2014: 2 · 2013: 3 · 2012: 4
FWCI
1.35
Type
journal article
Language
en
Open access
closed
Locations
  • European Journal of Organic Chemistry (publishedVersion)
  • Scuola Normale Superiore di Pisa (submittedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis of Indole Derivatives
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › melanin and skin pigmentation
Keywords
5,6-dihydroxyindole, eumelanin, biomimetic polymers, nanomaterials, π-electron systems, photophysical properties, organic synthesis, molecular design, optoelectronic properties

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