Chemoselective oxidative polymerization of m-ethynylphenol by peroxidase catalyst to a new reactive polyphenol

Biomacromolecules

Volumn 1, Issue 2, 2000, Pages 149-151

  Tonami, Hiroyuki ^a   Uyama, Hiroshi ^a   Kobayashi, Shiro ^a   Fujita, Takayuki ^b   Taguchi, Yoshihiro ^b   Osada, Katsuhisa ^b  

^a KYOTO UNIVERSITY   (Japan)

^b Mechatronic Devices Division 2   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HORSERADISH PEROXIDASE; M ETHYNYLPHENOL; M-ETHYNYLPHENOL; PHENOL DERIVATIVE; POLYMER;

ARTICLE; CATALYSIS; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; THERMOGRAVIMETRY;

CATALYSIS; HORSERADISH PEROXIDASE; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PHENOLS; POLYMERS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMOGRAVIMETRY;

EID: 0001677222     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm000005o     Document Type: Article

References (24)

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18. The following is a procedure for the polymerization. Under air, 1 (0.30 g, 2.5 mmol) and HRP (100 units/mg, 2.0 mg) in a mixture of 6.25 mL of methanol and 6.25 mL of 0.1 M phosphate buffer (pH 7) were placed in a 50 mL flask. Hydrogen peroxide (5% aqueous solution, 1.7 mL, 2.5 mmol) was added dropwise under gentle stirring to the mixture for 2 h at room temperature under air. After 3 h, polymer precipitates were collected by centrifugation. The polymer was washed with an aqueous methanol (50:50 vol %), followed by drying in vacuo to give 0.28 g of the polymer (yield 95 %).
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21. Reaction of phenylacetylene (2.5 mmol, 0.26 g) using HRP (1.0 mg) catalyst was carried out in a mixture of 8.75 mL of 1,4-dioxane and 3.75 mL of 0.1 M phosphate buffer (pH 7). Hydrogen peroxide (5% aqueous solution, 2.5 mmol) was added dropwise for 2 h. During the reaction, polymeric precipitates were not formed. In the HRR-catalyzed copolymerization of phenylacetylene (2.5 mmol, 0.26 g) and phenol (1.25 mmol, 0.12 g) under the similar reaction conditions, black powdery materials were precipitated, which were collected by centrifugation, followed by washing with an aqueous 1,4-dixoane to give 0.089 g of the polymer (75% yield based on phenol).
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