Research Article
BibTex RIS Cite

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

Year 2017, Volume: 6 Issue: 2, 773 - 784, 31.07.2017

Ersen Turaç

https://doi.org/10.28948/ngumuh.342077

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 (H2O2) 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 (1H and 13C
NMR), fourier transform infrared (FT-IR), gel permeation chromatography (GPC),
ultraviolet-visible (UV-Vis), cyclic voltammetry (CV) and thermogravimetric
analysis (TGA/DTG).

Keywords

Enzymatic oxidative polymerization Horseradish peroxidase hydrazone

References

  • [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.

ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ

Year 2017, Volume: 6 Issue: 2, 773 - 784, 31.07.2017

Ersen Turaç

https://doi.org/10.28948/ngumuh.342077

Abstract

   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 (H2O2) kullanılmıştır. Polimerleşme üzerine reaksiyon sıcaklığı, reaksiyon pH’sı
ve çözücü sistemleri gibi değişik parametrelerin etkileri çalışılmıştır.
Sentezlenen oligomerin karakterizasyonu nükleer magnetic rezonans (1H
ve 13C NMR), infrared spektroskopisi (FT-IR), jel geçirgenlik
kromotoğrafisi (GPC), ultraviyole spektroskopisi (UV-Vis), dönüşümlü voltametri
(CV) ve termogravimetrik analiz (TGA/DTA) teknikleri ile yapılmıştır.

Keywords

Enzimatik oksidatif polimerleşme horseradish peroksidaz hidrazon hidrojen peroksit

References

  • [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.
There are 38 citations in total.

Details

Subjects Chemical Engineering
Journal Section Others
Authors

Ersen Turaç 0000-0002-3543-4728

Publication Date July 31, 2017
Submission Date December 26, 2016
Acceptance Date April 11, 2017
Published in Issue Year 2017 Volume: 6 Issue: 2

Cite

APA Turaç, E. (2017). ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ. Niğde Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi, 6(2), 773-784. https://doi.org/10.28948/ngumuh.342077
AMA Turaç E. ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ. NOHU J. Eng. Sci. July 2017;6(2):773-784. doi:10.28948/ngumuh.342077
Chicago Turaç, Ersen. “ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ”. Niğde Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi 6, no. 2 (July 2017): 773-84. https://doi.org/10.28948/ngumuh.342077.
EndNote Turaç E (July 1, 2017) ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ. Niğde Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi 6 2 773–784.
IEEE E. Turaç, “ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ”, NOHU J. Eng. Sci., vol. 6, no. 2, pp. 773–784, 2017, doi: 10.28948/ngumuh.342077.
ISNAD Turaç, Ersen. “ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ”. Niğde Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi 6/2 (July 2017), 773-784. https://doi.org/10.28948/ngumuh.342077.
JAMA Turaç E. ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ. NOHU J. Eng. Sci. 2017;6:773–784.
MLA Turaç, Ersen. “ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ”. Niğde Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi, vol. 6, no. 2, 2017, pp. 773-84, doi:10.28948/ngumuh.342077.
Vancouver Turaç E. ENZİMATİK OKSİDATİF POLİMERİZASYON İLE ORTO-HİDRAZON-FONKSİYONLU OLİGOFENOL SENTEZİ. NOHU J. Eng. Sci. 2017;6(2):773-84.

23135