PMID- 18282186
OWN - NLM
STAT- MEDLINE
DCOM- 20080911
LR  - 20081121
IS  - 0031-8655 (Print)
IS  - 0031-8655 (Linking)
VI  - 84
IP  - 3
DP  - 2008 May-Jun
TI  - Synthesis and polymerization studies of organic-soluble eumelanins.
PG  - 632-8
LID - 10.1111/j.1751-1097.2007.00295.x [doi]
AB  - The isolation, structure determination and chemical characterization of 
      eumelanins has been plagued by their very low solubility in organic solvents. To 
      gain insights into the structure and reactivity of these unusual and important 
      biologic macromolecules and to pave the way for their use in electronics, we have 
      prepared soluble melanins via the synthesis of monomeric precursors containing 
      lipophilic substituents. Two such monomers derived from 
      5,6-dihydroxyindole-2-carboxylic acid (DHICA) were prepared, namely the benzyl 
      and octyl ester derivatives. Both benzyl and octyl ester monomers were 
      oxidatively polymerized to yield dark, melanin-like pigments. These 
      polymerization processes were followed by UV-visible, fluorescence and NMR 
      spectroscopy. These studies showed that the polymerizations proceeded by 
      cross-linking at the 4- and 7-positions of the indole nucleus and led to highly 
      heterogeneous polymeric products. Incorporation of a lipophilic benzyl or octyl 
      group resulted in enhanced solubility of the pigments in a wide range of organic 
      solvents. The UV-visible spectra of the organically soluble synthetic melanins 
      were essentially identical to that of natural eumelanin.
FAU - Lawrie, Kirsten J
AU  - Lawrie KJ
AD  - School of Molecular and Microbial Sciences, University of Queensland, Brisbane, 
      Queensland, Australia.
FAU - Meredith, Paul
AU  - Meredith P
FAU - McGeary, Ross P
AU  - McGeary RP
LA  - eng
PT  - Journal Article
DEP - 20080211
PL  - United States
TA  - Photochem Photobiol
JT  - Photochemistry and photobiology
JID - 0376425
RN  - 0 (Esters)
RN  - 0 (Indoles)
RN  - 0 (Melanins)
RN  - 0 (Polymers)
RN  - 12627-86-0 (eumelanin)
RN  - 4790-08-3 (5,6-dihydroxy-2-indolylcarboxylic acid)
SB  - IM
MH  - Chemistry, Organic
MH  - Esters/chemical synthesis/chemistry
MH  - Hydrogen-Ion Concentration
MH  - Indoles/chemistry
MH  - Magnetic Resonance Spectroscopy
MH  - Melanins/*chemical synthesis/chemistry
MH  - Molecular Structure
MH  - Organic Chemistry Phenomena
MH  - Polymers/chemical synthesis/*chemistry
MH  - Solubility
EDAT- 2008/02/20 09:00
MHDA- 2008/09/13 09:00
CRDT- 2008/02/20 09:00
PHST- 2008/02/20 09:00 [pubmed]
PHST- 2008/09/13 09:00 [medline]
PHST- 2008/02/20 09:00 [entrez]
AID - PHP295 [pii]
AID - 10.1111/j.1751-1097.2007.00295.x [doi]
PST - ppublish
SO  - Photochem Photobiol. 2008 May-Jun;84(3):632-8. doi: 
      10.1111/j.1751-1097.2007.00295.x. Epub 2008 Feb 11.