Synthesis, characterization, thermal stability and electrochemical properties of ortho-imine-functionalized oligophenol via enzymatic oxidative polycondensation

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dc.authoridGokturk, ersen/0000-0001-6742-2847
dc.authoridSahmetlioglu, Ertugrul/0000-0002-7324-0385
dc.contributor.authorKumbul, Altug
dc.contributor.authorGokturk, Ersen
dc.contributor.authorSahmetlioglu, Ertugrul
dc.date.accessioned2024-09-18T20:54:12Z
dc.date.available2024-09-18T20:54:12Z
dc.date.issued2016
dc.departmentHatay Mustafa Kemal Üniversitesien_US
dc.description.abstractOrtho-imine functionalized oligophenol was synthesized via enzymatic polymerization of 2-((4-nitrophenylimino) methyl) phenol (NPIMP). Enzymatic polymerization was catalyzed by Horseradish peroxidase (HRP) enzyme and hydrogen peroxide (H2O2) oxidizer yielded oligophenol with imine functionality on the side-chain. Effects of various factors including reaction pH, temperature and solvent system on the polymerization were studied. Optimum polymerization with the highest yield (96 %) and number-average molecular weight (M-n = 7300 g/mol, degree of polymerization approximate to 30) was accomplished using equivolume mixture of acetone/pH 7.0 phosphate buffer medium at 35 degrees C in 24 h under air. Characterization of the resulting oligomer was accomplished by ultraviolet-visible spectroscopy (UV-Vis), fourier transform infrared spectroscopy (FT-IR), H-1 and C-13 nuclear magnetic resonance (H-1 and C-13 NMR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltammetry (CV) and gel permeation chromatography (GPC). The polymerization involved elimination of hydrogen from NPIMP, and the oligomer possessed phenolic -OH end groups. The oligomer backbone was composed of oxyphenylene and phenylene repeat units. The optical band gaps (Eg) of NPIMP and oligo(NPIMP) were measured as 3.21 and 3.39 Eg, respectively. Thermal stability of the oligo(NPIMP) was also found to be relatively high, and lost 5 % of its mass at 175 degrees C and lost 50 % of its mass at 600 degrees C.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [115Z482]en_US
dc.description.sponsorshipThis research was partially supported by the Scientific and Technological Research Council of Turkey (TUBITAK) (115Z482).en_US
dc.identifier.doi10.1007/s10965-016-0953-1
dc.identifier.issn1022-9760
dc.identifier.issn1572-8935
dc.identifier.issue3en_US
dc.identifier.scopus2-s2.0-84958772107en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1007/s10965-016-0953-1
dc.identifier.urihttps://hdl.handle.net/20.500.12483/11667
dc.identifier.volume23en_US
dc.identifier.wosWOS:000439781600002en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringeren_US
dc.relation.ispartofJournal of Polymer Researchen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectPhenolen_US
dc.subjectEnzymatic polymerizationen_US
dc.subjectHorseradish peroxidase (HRP) enzymeen_US
dc.subjectOligophenolen_US
dc.subjectpHen_US
dc.subjectHydrogen peroxideen_US
dc.titleSynthesis, characterization, thermal stability and electrochemical properties of ortho-imine-functionalized oligophenol via enzymatic oxidative polycondensationen_US
dc.typeArticleen_US

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