Chemoenzymatic Polymerization of Hydrazone Functionalized Phenol


Isci I., Gokturk E., Turac E., Sahmetlioglu E.

POLYMER SCIENCE SERIES B, vol.58, no.4, pp.411-420, 2016 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 4
  • Publication Date: 2016
  • Doi Number: 10.1134/s1560090416040047
  • Journal Name: POLYMER SCIENCE SERIES B
  • Journal Indexes: Science Citation Index Expanded
  • Page Numbers: pp.411-420

Abstract

Hydrazone substituted oligophenol was synthesized via enzymatic oxidative polymerization of (E)-2-((2-phenylhydrazono) methyl) phenol. Enzymatic polymerization catalyzed by Horseradish peroxidase (HRP) enzyme and H2O2 oxidizer yielded oligophenol with hydrazone functionality on the side-chain. Effects of various factors including solvent system, reaction pH and temperature on the polymerization were studied. Optimum polymerization conditions with the highest yield (84%) and molecular weight (M-n = 8 x 103, DP approximate to 37, PDI - 1.11) was achieved using MeOH/pH 6.0 buffer (1 : 1 vol %) at 25 degrees C in 24 h under air. Synthesized oligomer was characterized by H-1 and C-13 NMR, FTIR, UV-Vis spectroscopy, GPC, cyclic voltammetry and thermo-gravimetric analyses. The polymerization involved hydrogen elimination from the monomer, and terminal units of the oligomer structure consisted of phenolic hydroxyl (-OH) end groups. The oligomer backbone possessed phenylene and oxyphenylene repeat units. The resulting oligomer was completely soluble in common organic solvents. The oligomer was thermally robust and exhibited 5% mass loss at 375 degrees C and 50% mass loss at 440 degrees C.