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Enzymatic Template Synthesis of Polyphenol

Published online by Cambridge University Press:  10 February 2011

Ferdinando F. Bruno
Affiliation:
Materials Science Team, Natick Soldier Center, U.S. Army Soldier, Biological, Chemical Command, Natick, MA 01760
Ramaswamy Nagarajan
Affiliation:
Departments of Physics and Chemistry, Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA 01854.
Jena S. Sidhartha
Affiliation:
Materials Science Team, Natick Soldier Center, U.S. Army Soldier, Biological, Chemical Command, Natick, MA 01760
Ke Yang
Affiliation:
Departments of Physics and Chemistry, Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA 01854.
Jayant Kumar
Affiliation:
Departments of Physics and Chemistry, Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA 01854.
Sukant Tripathy
Affiliation:
Departments of Physics and Chemistry, Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA 01854.
Lynne Samuelson
Affiliation:
Materials Science Team, Natick Soldier Center, U.S. Army Soldier, Biological, Chemical Command, Natick, MA 01760
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Abstract

An alternative, biocatalytic approach for the synthesis of a new class of water soluble and processable polyphenols is presented. In this approach, the enzyme horseradish peroxidase (HRP) is used to polymerize phenol in the presence of an ionic template. The template serves as a surfactant that can both emulsify the phenol monomer and growing polyphenol chains and provide water solubility of the final polyphenol/template complex. This approach is a simple, one step synthesis where the reaction conditions are remarkably mild and environmentally compatible. The final product is a water soluble, high molecular weight complex of polyphenol and the template used. The approach is also very versatile as numerous templates may be used to build in specific functionalities to the final polyphenol complex. Polystyrene sulfonates (SPS), lignin sulfonate and dodecyl benzene sulfonates (micelles) are the templates investigated in this study. Thermal analysis and UV-Vis spectroscopy shows that these complexes have exceptional thermal stability and a high degree of backbone conjugation. Electrical conductivities on the order of 10−5 S/cm and third order nonlinear optical susceptibilities (χ(3)) of 10−12 esu are also observed. In the case of the SPS template, under certain conditions, a sol gel complex may be formed. This enzymatic approach offers interesting opportunities in the synthesis and functionalization of a new class of processable polyphenolic materials.

Type
Research Article
Copyright
Copyright © Materials Research Society 2000

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References

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