An investigation of the enzymatic oligomerization of nitro-substituted phenylene diamine: Thermal and fluorescence properties

Year 2024, , 153 - 164, 31.08.2024

Feyza Kolcu

https://doi.org/10.54187/jnrs.1527152

Abstract

2-nitro-p-phenylenediamine, an aromatic diamine, was studied for its oxidative oligomerization with H2O2 using enzyme-catalyzed oligomer synthesis. Characterization of molecular structures was performed utilizing ultraviolet-visible (UV-Vis) spectrophotometer, Fourier-transform infrared spectroscopy (FT-IR), and nuclear magnetic resonance (NMR) techniques, identifying phenazine-bridged oligomer resulting from the enzymatic oligomerization process. Based on the results of gel permeation chromatography (GPC) analysis, the synthesized compound was identified as being in an oligomeric form. Conversely, the number of repeating units, as determined by Mw, was found to be 28. The solvent effect on the optical features of the synthesized oligomer in polar solvents was analyzed. The degradation of phenazine-type structures in the oligomer occurred at higher temperatures than that of the monomer. Under visible light excitation, the oligomer exhibited green light emission with a quantum yield (QY) of 6.2% in N,N-dimethylformamide (DMF). 2-nitro-p-phenylenediamine was readily oxidized into an oligomer with ortho-coupled constitutional units, having a lower electrochemical band gap than the monomer, via the enzymatic oligomerization route. Scanning electron microscopy revealed that enzyme-catalyzed oxidation of monomers exhibited a spongy morphology with some pores

Keywords

p-phenylenediamine, Horseradish peroxidase, Enzyme-catalyzed oligomerization, Green photoluminescence emission, Limiting oxygen index

Ethical Statement

No approval from the Board of Ethics is required.

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