M. Reihmann, H. Ritter
Jan 12, 2002
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0
Influential Citations
11
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Journal
Journal of Macromolecular Science, Part A
Abstract
ABSTRACT Results on the regioselective enzymatic polymerization of 4-amino-phenol (1) are reported. The HRP-catalyzed treatment of unprotected 4-amino-phenol (1) with hydrogen peroxide results mainly in the formation of [1,4]benzochinone-monoimine (6). In contrast, it was possible to build up phenol polymers, which had relatively high molecular masses, via protection of 1 with 4-nitro-benzaldehyde (2) leading to 4-(4-nitro-benzylidenamino)-phenol (3). The polymer-analogous deprotection of the phenol polymers was performed by treatment with THF/HCl and confirmed by FT-IR, 1H-NMR and UV-Vis analysis. As a result, electrical conducting poly(4-amino-phenol) was obtained, which should have potential application as a redox active polymer, as shown by cyclic voltammetry measurements. Additionally, detailed studies concerning the structure of the phenol polymers 4 and 5 were performed with 1H-NMR, 13C-NMR and FT-IR spectroscopy. Aborting the polymerization process by adding bovine liver catalase at an early stage made it possible to synthesize dimers of 3. This finding allowed a more precise description of the polymeric structure and provides a clearer view of the polymerization mechanism.