Elucidating the structure of poly(dopamine)

Langmuir. 2012 Apr 17;28(15):6428-35. doi: 10.1021/la204831b. Epub 2012 Apr 4.


Herein we propose a new structure for poly(dopamine), a synthetic eumelanin that has found broad utility as an antifouling agent. Commercially available 3-hydroxytyramine hydrochloride (dopamine HCl) was polymerized under aerobic, aqueous conditions using tris(hydroxymethyl)aminomethane (TRIS) as a basic polymerization initiator, affording a darkly colored powder product upon isolation. The polymer was analyzed using a variety of solid state spectroscopic and crystallographic techniques. Collectively, the data showed that in contrast to previously proposed models, poly(dopamine) is not a covalent polymer but instead a supramolecular aggregate of monomers (consisting primarily of 5,6-dihydroxyindoline and its dione derivative) that are held together through a combination of charge transfer, π-stacking, and hydrogen bonding interactions.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biological Products / chemistry
  • Indoles / chemistry*
  • Magnetic Resonance Spectroscopy
  • Melanins / chemistry
  • Polymers / chemistry*
  • Spectroscopy, Fourier Transform Infrared


  • Biological Products
  • Indoles
  • Melanins
  • Polymers
  • polydopamine
  • eumelanin