title: Elucidating the structure of poly(dopamine).
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station, A1590 Austin, Texas, USA.
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Dreyer
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Miller
authors.forename: Benny D
authors.initials: BD
authors.lastname: Freeman
authors.forename: Donald R
authors.initials: DR
authors.lastname: Paul
authors.forename: Christopher W
authors.initials: CW
authors.lastname: Bielawski
mesh_terms: D001688:Biological Products / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008543:Melanins / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D001688:Biological Products; D007211:Indoles; D008543:Melanins; D011108:Polymers; C568283:polydopamine; C041877:eumelanin