Chemoenzymatic synthesis of a poly(hydroquinone)

Tonami, Hiroyuki; Uyama, Hiroshi; Kobayashi, Shiro; Rettig, Karsten; Ritter, Helmut

doi:10.1002/(sici)1521-3935(19990901)200:9<1998::aid-macp1998>3.0.co;2-6

Cited by 34 publications

(22 citation statements)

References 18 publications

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“…Figure shows effects of the buffer pH on yield and molecular weight of the oligomer in 1,4‐dioxane at 35°C. These results indicate that reaction pH strongly affects the polymerization yield and molecular weight …”

Section: Resultsmentioning

confidence: 77%

Enzymatic oxidative polymerization of para‐imine functionalized phenol catalyzed by horseradish peroxidase

Kümbül

Göktürk

Turaç

et al. 2015

Polymers for Advanced Techs

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Enzymatic oxidative polymerization of a new para‐imine functionalized phenol derivative, 4‐(4‐hydroxybenzylideneamino)benzoic acid (HBBA), using horseradish peroxidase enzyme and hydrogen peroxide oxidizer has been investigated in an equivolume mixture of an organic solvent (acetone, methanol, ethanol, dimethylformamide, 1,4‐dioxane, and tetrahydrofuran) and phosphate buffer (pH = 5.0, 6.0, 6.8, 7.0, 7.2, 8.0, and 9.0) at different temperatures under air for 24 h. The resulting oligomer, oligo(4‐(4‐hydroxybenzylideneamino)benzoic acid) [oligo(HBBA)], was characterized using ultraviolet–visible, Fourier transform infrared (FT‐IR), 1H nuclear magnetic resonance (NMR), cyclic voltammetry, size exclusion chromatography, differential scanning calorimetry, and thermogravimetric analyses. Polymerization involved carbon dioxide and hydrogen elimination from the monomer, and terminal units of the oligomer structure consisted of phenolic hydroxyl (–OH) groups at the ends. The polymer is mainly composed of a mixture of phenylene and oxyphenylene units according to 1H NMR and FT‐IR analyses. Effects of solvent system, temperature and buffer pH on the polymerization have been investigated in respect to the yield and molecular weight (Mn) of the product. The best condition in terms of the highest molecular weight (Mn = 3000 g/mol, DP ~ 15) was achieved in an equivolume mixture of 1,4‐dioxane/pH 5.0 phosphate buffer condition at 35°C. Electrochemical characterization of oligo(HBBA) was investigated at different scan rates. The resulting oligomer has also shown relatively high thermal stability according to thermogravimetric analysis. Copyright © 2015 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 77%

Enzymatic oxidative polymerization of para‐imine functionalized phenol catalyzed by horseradish peroxidase

Kümbül

Göktürk

Turaç

et al. 2015

Polymers for Advanced Techs

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“…The resulting polymer was used for a glucose sensor exploiting its good redox properties [53] . Another route for the chemoenzymatic synthesis of poly(hydroquinone) was the SBP -catalyzed polymerization of 4 -hydroxyphenyl benzoate, followed by alkaline hydrolysis [54] .…”

Section: Peroxidase -Catalyzed Synthesis Of Functional Phenolic Polymersmentioning

confidence: 99%

Enzymatic Polymerization of Phenolic Monomers

Uyama

2010

Biocatalysis in Polymer Chemistry

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“…Chemo-enzymatic synthesis of a polymer containing hydroquinone units was achieved by the SBP-catalyzed polymerization of 4-hydroxyphenyl benzoate, followed by alkaline hydrolysis. [212] Urushi, a natural crosslinked material from a phenolic monomer, is a typical Japanese traditional coating showing excellent toughness and brilliance for a long period of time. In the early days of the last century, pioneering works by Majima revealed that the mainly important components of urushi are ''urushiols'', a catechol derivative directly linked to unsaturated hydrocarbon chains consisting of a mixture of monoenes, dienes, and trienes at 3-or 4-position of catechol (Scheme 45).…”

Section: Phenolic Polymersmentioning

confidence: 99%

Biomacromolecules and Bio‐Related Macromolecules

Kobayashi

Uyama

2003

Macro Chemistry & Physics

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The present article briefly reviews research developments in the area of biomacromolecules and bio‐related macromolecules, whose research papers have been published for several decades preferably in the Macromolecular Journals. The area covers the important classes of macromolecules, polysaccharides (cellulose, amylose, chitin, etc.), polyesters (poly(lactic acid), poly(hydroxyalkanoate)s, etc.), and phenolic polymers (lignin, urushi, etc.). These polymers and their derivatives are very important for scientific interests as well as for industrial applications. Their synthesis, structure, reactions, and properties are mainly mentioned, and important topics of the target polymers are selected and mostly chronologically reviewed.

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Chemoenzymatic synthesis of a poly(hydroquinone)

Cited by 34 publications

References 18 publications

Enzymatic oxidative polymerization of para‐imine functionalized phenol catalyzed by horseradish peroxidase

Enzymatic oxidative polymerization of para‐imine functionalized phenol catalyzed by horseradish peroxidase

Enzymatic Polymerization of Phenolic Monomers

Biomacromolecules and Bio‐Related Macromolecules

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