SavedAdd your journal

Journals / Niğde Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi / 2017 / Cilt: 6 Sayı: 2

SYNTHESIS OF ORTHO-HYDRAZONE-FUNCTIONALIZED OLIGOPHENOL VIA ENZYMATIC OXIDATIVE POLYMERIZATION

ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ

Ersen Turaç0000-0002-3543-4728
Pages
773–784
Publication Date
2017-07-31
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Synthesized oligomer was characterized by nuclear magnetic resonance ( 1 H and 13 C NMR), fourier transform infrared (FT-IR), gel permeation chromatography (GPC), ultraviolet-visible (UV-Vis), cyclic voltammetry (CV) and thermogravimetric analysis (TGA/DTG).

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Hydrazone substituted oligophenol was synthesized via enzymatic oxidative polymerization of (E) -2-(1-(2-phenylhydrazono)ethyl)phenol [PHEP].
📊
Key Findings & Data:Enzymatic polymerization catalyzed by Horseradish peroxidase (HRP) enzyme and hydrogen peroxide (H 2 O 2 ) oxidizer yielded oligophenol with hydrazone functionality on the side-chain.
💡
Conclusion & Impact:Synthesized oligomer was characterized by nuclear magnetic resonance ( 1 H and 13 C NMR), fourier transform infrared (FT-IR), gel permeation chromatography (GPC), ultraviolet-visible (UV-Vis), cyclic voltammetry (CV) and thermogravimetric analysis (TGA/DTG).
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Enzimatik oksidatif polimerleşme · horseradish peroksidaz · hidrazon

Abstract

Hydrazone substituted oligophenol was synthesized via enzymatic oxidative polymerization of (E) -2-(1-(2-phenylhydrazono)ethyl)phenol [PHEP]. Enzymatic polymerization catalyzed by Horseradish peroxidase (HRP) enzyme and hydrogen peroxide (H 2 O 2 ) 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. Synthesized oligomer was characterized by nuclear magnetic resonance ( 1 H and 13 C NMR), fourier transform infrared (FT-IR), gel permeation chromatography (GPC), ultraviolet-visible (UV-Vis), cyclic voltammetry (CV) and thermogravimetric analysis (TGA/DTG).

Özet

Hidrazon fonksiyonlu oligofenol, (E) -2-(1-(2-fenilhidrazon)etil)fenol [FHEF] enzimatik oksidatif polimerizasyon yöntemiyle sentezlenmiştir. Yan zincirinde hidrazon fonksiyonel grubu içeren fenol türevinin enzimatik oksidatif polimerizasyonunda; katalizör olarak Horseradish peroksidaz (HRP) enzimi, yükseltgeyici olarak ise Hidrojen peroksit ( H 2 O 2 ) kullanılmıştır. Polimerleşme üzerine reaksiyon sıcaklığı, reaksiyon pH’sı ve çözücü sistemleri gibi değişik parametrelerin etkileri çalışılmıştır. Sentezlenen oligomerin karakterizasyonu nükleer magnetic rezonans ( 1 H ve 13 C NMR), infrared spektroskopisi (FT-IR), jel geçirgenlik kromotoğrafisi (GPC), ultraviyole spektroskopisi (UV-Vis), dönüşümlü voltametri (CV) ve termogravimetrik analiz (TGA/DTA) teknikleri ile yapılmıştır.

🔖

Cite This Article

Turaç, E. (2017). SYNTHESIS OF ORTHO-HYDRAZONE-FUNCTIONALIZED OLIGOPHENOL VIA ENZYMATIC OXIDATIVE POLYMERIZATION. Niğde Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi, Cilt: 6 Sayı: 2, 773–784. https://doi.org/10.28948/ngumuh.342077

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (38)

  1. KOBAYASHI, S., “Green Polymer Chemistry: New Methods of Polymer Synthesis Using Renewable Starting Materials”, Structural Chemistry, 28(2), 461-474, 2016.
  2. DORDICK, J.S., MARLETTA, M.A., KLIBANOV, A.M., “Polymerization of Phenols Catalyzed by Peroxidase in Nonaqueous Media”, Biotechnology and Bioengineering, 30(1), 31-36, 1987.
  3. ZERVA, A., MANOS, N., VOUYIOUKA, S., CHRISTAKOPOULOS, P., TOPAKAS, E., “Bioconversion of Biomass-Derived Phenols Catalyzed by Myceliophthora thermophila Laccase”, Molecules, 21(5), 550, 2016.
  4. GAO, Y., JIANG, F., ZHANG, L., CUI, Y., “Enzymatic Synthesis of Polyguaiacol and its Thermal Antioxidant Behavior in Polypropylene”, Polymer Bulletin, 73, 1343–1359, 2016.
  5. KUMBUL, A., GOKTURK, E., SAHMETLIOGLU, E., “Synthesis, Characterization, Thermal Stability and Electrochemical Properties of Ortho-Imine-Functionalized oligophenol via Enzymatic Oxidative Polycondensation”, Journal of Polymer Research 23, 52, 2016.
  6. NANAYAKKARA, S., ZHAO, Z., PATTI, A.F., HE, L., SAITO, K., “Immobilized Horseradish Peroxidase (I-HRP) as Biocatalyst for Oxidative Polymerization of 2,6-Dimethylphenol”, ACS Sustainable Chemistry Engineering, 2(8), 1947−1950, 2014.
  7. UYAMA, H., LOHAVISAVAPANICH, C., IKEDIA, R., KOBAYASHI, S., “Chemoselective Polymerization of a Phenol Derivative Having a Methacryl Group by Peroxidase Catalyst”, Macromolecules, 31, 554-556, 1998.
  8. NABID, M.R., ENTEZAMI, A.A., “Enzymatic Synthesis and Characterization of a Water-Soluble, Conducting Poly(o-toluidine)”, European Polymer Journal, 39, 1169-1175, 2003.
  9. NABID, M.R., ENTEZAMI, A.A., “Synthesis of Water-soluble and Conducting Poly(2-ethylaniline) by Using Horseradish Peroxidase”, Iranian Polymer Journal, 12(5), 401-406, 2003.
  10. MOULAY, S., “Polymers with Dihydroxy/Dialkoxybenzene Moieties”, Comptes Rendus Chimie, 12, 577-601, 2009.
  11. PRADEEP, N.V., ANUPAMA, A., HAMPANNAVAR, U.S., “Polymerization of Phenol using Free and Immobilized Horseradish Peroxidase”, Journal of Environment and Earth Science, 2(1), 31-36, 2012.
  12. NARAYAN, A.V., PUSHPA, A., “Enzyme Based Processes for Removal of Phenol from Waste Water: Current Status and Future Challenges”, Journal of Environmental Research and Development, 7(2), 724-728, 2012.
  13. SU, X., APRAHAMIAN, I., “Hydrazone-based Switches, Metallo-Assemblies and Sensors”, Chemical Society Reviews, 43, 1963-1981, 2014.
  14. BRINKHUIS, R.P., VISSER, T.R., RUTJES, F.P.J.T., VAN HEST, J.C.M., “Shedding the Hydrophilic Mantle of Polymersomes”, Polymer Chemistry, 2, 550–552, 2011.
  15. GU, Z., “Bioinspired and Biomimetic Polymer Systems for Drug and Gene Delivery”, Wiley-VCH Verlag GmbH & Co. KGaA, 2014.
  16. YILDIRIM, P., GOKTURK, E., TURAC, E., DEMIR, H.O., SAHMETLIOGLU, E., “Chemoenzymatic Polycondensation of Para-Benzylamino Phenol”, Chemical Papers, 70(5), 610–619, 2016.
  17. SAHMETLIOGLU, E., MART, H., YURUK, H., SURME, Y., “Synthesis and Characterization of Oligosalicylaldehyde-Based Epoxy Resins”, Chemical Papers, 60(1), 65-68, 2006.
  18. SHAN, J.N., HAN, L.Y., BAI, F.L., CAO, S.K., “Enzymatic Polymerization of Aniline and Phenol Derivatives Catalyzed by Horseradish Peroxidase in Dioxane(II)”, Polymers for Advanced Technologies, 14, 330–336, 2003.
  19. KOLCU, F., KAYA, I., “Synthesis and Characterization of Conjugated Polyphenols Derived from Azomethine Formation Containing Terephtaldehyde via Oxidative Polycondensation”, Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 53(7), 438-451, 2016.
  20. DOGAN, F., KAYA, I., TEMIZKAN, K., “Multi-response Behavior of Aminosulfonaphthole System”, Journal of Molecular Catalysis B: Enzymatic, 133, 234–245, 2016.
  21. LIU, W., BIAN, S., LI, L., SAMUELSON, L., KUMAR, J., TRIPATHY, S., “Enzymatic Synthesis of Photoactive Poly(4-phenylazophenol)”, Chemistry of Materials, 12(6), 1577-1584, 2000.
  22. KOBAYASHI, S., HIGASHIMURA, H., “Oxidative Polymerization of Phenols Revisited”, Progress in Polymer Science, 28, 1015-1048, 2003.
  23. MITA, N., TAWAKI, S.I., UYAMA, H., KOBAYASHI, S., “Enzymatic Oxidative Polymerization of Phenol in an Aqueous Solution in the Presence of a Catalytic Amount of Cyclodextrin”, Macromolecular Bioscience, 2(3), 127-130, 2002.
  24. IKEDA, R., SUGIHARA, J., UYAMA, H., KOBAYASHI, S., “Enzymatic Oxidative Polymerization of 4-Hydroxybenzoic acid Derivatives to Poly(phenylene oxide)s”, Polymer International, 47(3), 295-301, 1998.
  25. ZHENG, K., ZHANG, L., GAO, Y., WU, Y., ZHAO, W., CUI, Y., “Enzymatic Oxidative Polymerization of Pyrogallic acid for Preparation of Hindered Phenol Antioxidant”, Journal of Applied Polymer Science, 132(12), 41591, 2015.
  26. ISCI, I., GOKTURK, E., TURAC, E., SAHMETLIOGLU, E., “Chemoenzymatic Polymerization of Hydrazone Functionalized Phenol”, Polymer Science, Series B, 58(4), 411–420, 2016.
  27. DINESHKUMAR, S., MUTHUSAMY, A., CHANDRASEKARAN, J., “Temperature and Frequency Dependent Dielectric Properties of Electrically Conducting Oxidatively Synthesized Polyazomethines and their Structural, Optical, and Thermal Characterizations”, Journal of Molecular Structure, 1128, 730-740, 2017.
  28. KOCAK, A., KUMBUL, A., GOKTURK, E., SAHMETLIOGLU, E., “Synthesis and Characterization of Imine-Functionalized Polyphenol via Enzymatic Oxidative Polycondensation of a Bisphenol Derivative”, Polymer Bulletin, 73(1), 163–177, 2016.
  29. KUPRIYANOVICH, Y.N., SUKHOV, B.G., MEDVEDEVA, S.A., MIKHALEVA, A.I., VAKUL’SKAYA, T.I., MYACHINA, G.F., TROFIMOV, B.A., “Peroxidase-Catalysed Synthesis of Electroconductive Polypyrrole”, Mendeleev Communications, 18(1), 56-58, 2008.
  30. TURAC, E., SURME, Y., SAHMETLIOGLU, E., VAROL, R., NARIN, I., TOPPARE, L., “Synthesis and characterization of Water-Soluble Oligosalicylaldehyde-Sulfanilic Acid and Its Cu(II), Co(II), Pb(II) Complexes”, Journal of Applied Polymer Science, 110, 564-568, 2008.
  31. CHANDRASEKHAR, P., “Conducting Polymers, Fundamentals and Applications: A Practical Approach”, Springer US, 1999.
  32. SKOTHEIM, T.A., ELSENBAUMER, R.L., REYNOLDS, J.R., “Handbook of Conducting Polymers”, Second Edition; Marcel Dekker inc., New York, 1998.
  33. AK, M., GANCHEVA, V., TERLEMEZYAN, L., TANYELI, C., TOPPARE, L., “Synthesis Of A Dipyrromethane Functionalized Monomer And Optoelectrochromic Properties of Its Polymer”, European Polymer Journal, 44, 2567–2573, 2008.
  34. SARANYA, K., RAMEEZ, M.D., SUBRAMANIA, A., “Developments in Conducting Polymer Based Counter Electrodes for Dye-Sensitized Solar Cells – An overview”, European Polymer Journal, 66, 207–227, 2015.
  35. ABD-EL-AZIZ, A.S., DALGAKIRAN, S.S., BICHLER, L., “Novel Synthesis and Electropolymerization of Metallo-Conjugated Thiophene Derivatives”, European Polymer Journal, 48, 1901–1913, 2012.
  36. TURAC, E., SAHMETLIOGLU, E., DEMIRCAN, A., TOPPARE, L., “Synthesis and Characterization of Conducting Copolymer of Trans-1-(4-methyl-3′-thienyl)-2-(ferrocenyl)ethene with EDOT”, Journal of Applied Polymer Science, 126, 808–814, 2012.
  37. TURAC, E., AK, M., SAHMETLIOGLU, E., SENER, M.K., KAYA, M.A., “Synthesis and Characterization of poly{2-[3-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole} and Its Copolymer with EDOT”, Russian Journal of General Chemistry, 81(12), 2510–2516, 2011.
  38. KUMBUL, A., GOKTURK, E., TURAC, E., SAHMETLİOGLU, E., “Enzymatic Oxidative Polymerization of Para-Imine Functionalized Phenol Catalyzed by Horseradish Peroxidase”, Polymers for Advanced Technologies, 26(9), 1123-1129, 2015.