Enzymatic synthesis of soluble phenol polymer in water using anionic surfactant as additive

Zhang, Lei; Zhang, Yudong; Xue, Yingying; Duan, Hua; Cui, Yuanchen

doi:10.1002/pi.4411

Cited by 15 publications

(7 citation statements)

References 30 publications

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“…For the HRP-catalyzed polymerization of phenol, sodium dodecylbenzenesulfonate was used to produce the polymer in high yields over a wide pH range from 4 to 10 . The polymer showed good solubility toward organic solvents such as DMF, DMSO, acetone, and THF …”

Section: Oxidoreductasesmentioning

confidence: 99%

“…144 The polymer showed good solubility toward organic solvents such as DMF, DMSO, acetone, and THF. 145 Ionic liquids are effective as cosolvent for the enzymatic oxidative polymerization of phenols. In a mixture of a phosphate buffer and 1-butyl-3-methylimidazolium tetrafluoroborate or 1-butyl-3-methylpyridinium tetrafluoroborate, pcresol, 1-naphthol, 2-naphthol, and p-phenylphenol were polymerized by SBP to give the polymers in good yields.…”

Section: Peroxidasesmentioning

confidence: 99%

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Enzymes as Green Catalysts for Precision Macromolecular Synthesis

et al. 2016

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The present article comprehensively reviews the macromolecular synthesis using enzymes as catalysts. Among the six main classes of enzymes, the three classes, oxidoreductases, transferases, and hydrolases, have been employed as catalysts for the in vitro macromolecular synthesis and modification reactions. Appropriate design of reaction including monomer and enzyme catalyst produces macromolecules with precisely controlled structure, similarly as in vivo enzymatic reactions. The reaction controls the product structure with respect to substrate selectivity, chemo-selectivity, regio-selectivity, stereoselectivity, and choro-selectivity. Oxidoreductases catalyze various oxidation polymerizations of aromatic compounds as well as vinyl polymerizations. Transferases are effective catalysts for producing polysaccharide having a variety of structure and polyesters. Hydrolases catalyzing the bond-cleaving of macromolecules in vivo, catalyze the reverse reaction for bond forming in vitro to give various polysaccharides and functionalized polyesters. The enzymatic polymerizations allowed the first in vitro synthesis of natural polysaccharides having complicated structures like cellulose, amylose, xylan, chitin, hyaluronan, and chondroitin. These polymerizations are "green" with several respects; nontoxicity of enzyme, high catalyst efficiency, selective reactions under mild conditions using green solvents and renewable starting materials, and producing minimal byproducts. Thus, the enzymatic polymerization is desirable for the environment and contributes to "green polymer chemistry" for maintaining sustainable society.

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Section: Oxidoreductasesmentioning

confidence: 99%

Section: Peroxidasesmentioning

confidence: 99%

Enzymes as Green Catalysts for Precision Macromolecular Synthesis

et al. 2016

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“…Increasing the organic solvent content, increases the molecular weight, however, the polymer yield will also decrease due to the HRP denaturation in organic solvents . During last decade, ionic surfactants, polyelectrolytes, and ionic liquids were used to obtain higher molecular weight water soluble polyphenols with enzyme catalysis. Nevertheless, in this work, the ethanol content was retained at 10% and polymer molecular weight was limited to less than 1500 Daltons.…”

Section: Resultsmentioning

confidence: 99%

Facile enzymatic preparation of fluorescent conjugated polymers of phenols and their application in sensing

Kiratitanavit

Bruno

Kumar

et al. 2018

J of Applied Polymer Sci

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The recognized drawback of utilizing metal catalysts for the synthesis of fluorescent conjugated polymers (CP) is the requirement for extensive purification to ensure complete removal of residual catalyst that would otherwise quench the fluorescence. In addition, typical synthesis of fluorescent CP involves multiple steps, monomers and solvents with varying levels of toxicity. This work demonstrates the possibility of utilizing oxidoreductase enzymes as the catalyst, for the one step polymerization of naturally occurring phenols to yield fluorescent conjugated polyphenols. The metal in the active site of the enzyme remains chelated during the synthesis allowing the polymers to be fluorescent as synthesized without the need for extensive purification. Three natural phenols, 4‐hydroxyphenylacetic acid, hydroxytyrosol, and chlorogenic acid were polymerized using Horseradish peroxidase as the biocatalyst. Spectroscopic techniques, UV–vis, Fourier transform infrared Spectroscopy–Attenuated Total Reflectance, and fluorescence, are used to characterize chemical structure and photoluminescence of these polymers. The polyphenols exhibit fluorescence with significant stokes shift in the range 30–100 nm rendering them useful in fluorescence quenching‐based sensors. Preliminary studies on use of these polymers, in the detection of nitro‐aromatic compounds in solution through using fluorescence‐quenching are also presented. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46496.

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“…Recently, the efficient enzymatic polymerization of phenol in aqueous solution was developed in the presence of templates, such as poly (ethylene oxide) (PEG) [34,35], cyclodextrin derivates [36,37], or surfactant [38,39]. The polymerization is fast and moderate without toxic formaldehyde.…”

Section: Introductionmentioning

confidence: 99%

Core–Shell Structured Phenolic Polymer@TiO2 Nanosphere with Enhanced Visible-Light Photocatalytic Efficiency

Zhang

et al. 2020

Nanomaterials

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Core–shell structured TiO2 is a promising solution to promote the photocatalytic effectiveness in visible light. Compared to metal or semiconductor materials, polymers are rarely used as the core materials for fabricating core–shell TiO2 materials. A novel core–shell structured polymer@TiO2 was developed by using phenolic polymer (PP) colloid nanoparticles as the core material. The PP nanoparticles were synthesized by an enzyme-catalyzed polymerization in water. A subsequent sol–gel and hydrothermal reaction was utilized to cover the TiO2 shell on the surfaces of PP particles. The thickness of the TiO2 shell was controlled by the amount of TiO2 precursor. The covalent connection between PP and TiO2 was established after the hydrothermal reaction. The core–shell structure allowed the absorption spectra of PP@TiO2 to extend to the visible-light region. Under visible-light irradiation, the core–shell nanosphere displayed enhanced photocatalytic efficiency for rhodamine B degradation and good recycle stability. The interfacial C–O–Ti bonds and the π-conjugated structures in the PP@TiO2 nanosphere played a key role in the quick transfer of the excited electrons between PP and TiO2, which greatly improved the photocatalytic efficiency in visible light.

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Enzymatic synthesis of soluble phenol polymer in water using anionic surfactant as additive

Cited by 15 publications

References 30 publications

Enzymes as Green Catalysts for Precision Macromolecular Synthesis

Enzymes as Green Catalysts for Precision Macromolecular Synthesis

Facile enzymatic preparation of fluorescent conjugated polymers of phenols and their application in sensing

Core–Shell Structured Phenolic Polymer@TiO2 Nanosphere with Enhanced Visible-Light Photocatalytic Efficiency

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