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Chemoenzymatic polycondensation of para-benzylamino phenol

  • Pinar Yildirim , Ersen Gokturk , Ersen Turac , Haci O Demir and Ertugrul Sahmetlioglu EMAIL logo
Published/Copyright: February 11, 2016
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Chemical Papers
From the journal Chemical Papers Volume 70 Issue 5

para-Benzylamine substituted oligophenol was synthesized via enzymatic oxidative polycondensation of 4-(benzylamino)phenol (BAP). Polymerization involved only the phenolic moiety without oxidizing the sec-amine (benzylamine) group. Chemoselective polycondensation of BAP monomer using HRP enzyme yielded oligophenol with sec-amine functionality on the side-chain. Effects of various factors including solvent system, reaction pH and temperature on the polycondensation were studied. Optimum polymerization process with the highest yield (63 %) and molecular weight (Mn = 5000, degree of polymerization ≈ 25) was achieved using the EtOH/ buffer (pH 5.0; 1 : 1 vol. ratio) at 25 °C in 24 h under air. Characterization of the oligomer was accomplished by 1H NMR and 13C NMR, Fourier transform infrared spectroscopy (FT-IR), gel permeation chromatography (GPC), ultraviolet-visible spectroscopy (UV-Vis), cyclic voltammetry (CV) and thermogravimetric analysis (TGA). The polymerization process involved the elimination of hydrogen from BAP, and phenolic-OH end groups of the oligo(BAP), confirmed using 1H NMR and FT-IR analyses. The oligomer backbone possessed phenylene and oxyphenylene repeat units, and the resulting oligomer was highly soluble in common organic solvents such as acetone, CHCl3, 1,4-dioxane, N,N-dimethylformamide (DMF), tetrahydrofurane (THF) and dimethylsulfoxide (DMSO). Oligo(BAP) was thermally stable and exhibited 5 % and 50 % mass loss determined by thermogravimetric analysis at 247°C and 852°C, respectively.

Keywords: enzymatic oxidative polymerization; horseradish peroxidase enzyme; oligophenol; hydrogen peroxide

Acknowledgements.

Ersen Gokturk would like to acknowledge the Turkish Ministry of National Education for his Ph.D. scholarship.

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Received: 2015-7-31
Revised: 2015-10-6
Accepted: 2015-10-7
Published Online: 2016-2-11
Published in Print: 2016-5-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.1515/chempap-2015-0242
Keywords for this article
enzymatic oxidative polymerization; horseradish peroxidase enzyme; oligophenol; hydrogen peroxide

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  1. Original Paper
  2. Preparation and characterisation of gelatine hydrogels predisposed to use as matrices for effective immobilisation of biocatalystst‡
  3. Original Paper
  4. Photocatalytic reduction of nitro aromatic compounds to amines using a nanosized highly active CdS photocatalyst under sunlight and blue LED irradiation
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  15. Original Paper
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  19. Original Paper
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