Chemoenzymatic polycondensation of para-benzylamino phenol

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dc.authorid0000-0002-7324-0385
dc.authorid0000-0002-2078-010X
dc.contributor.authorYildirim, Pinar
dc.contributor.authorGokturk, Ersen
dc.contributor.authorTurac, Ersen
dc.contributor.authorDemir, Haci O.
dc.contributor.authorSahmetlioglu, Ertugrul
dc.date.accessioned2019-08-01T13:38:39Z
dc.date.available2019-08-01T13:38:39Z
dc.date.issued2016
dc.departmentNiğde ÖHÜ
dc.description.abstractpara-Benzylamine substituted oligophenol was synthesized via enzymatic oxidative polycondensation of 4-(benzylamino) phenol (BAP). Polymerization involved only the phenolic moiety without oxidizing the sec-amine (benzylamine) group. Chemoselective polycondensation of BAP monomer using HRP enzyme yielded oligophenol with sec-amine functionality on the side-chain. Effects of various factors including solvent system, reaction pH and temperature on the polycondensation were studied. Optimum polymerization process with the highest yield (63 %) and molecular weight (M-n = 5000, degree of polymerization approximate to 25) was achieved using the EtOH/buffer (pH 5.0; 1 : 1 vol. ratio) at 25 degrees C in 24 h under air. Characterization of the oligomer was accomplished by H-1 NMR and C-13 NMR, Fourier transform infrared spectroscopy (FT-IR), gel permeation chromatography (GPC), ultraviolet-visible spectroscopy (UV-Vis), cyclic voltammetry (CV) and thermogravimetric analysis (TGA). The polymerization process involved the elimination of hydrogen from BAP, and phenolic -OH end groups of the oligo(BAP), confirmed using H-1 NMR and FT-IR analyses. The oligomer backbone possessed phenylene and oxyphenylene repeat units, and the resulting oligomer was highly soluble in common organic solvents such as acetone, CHCl3, 1,4-dioxane, N, N-dimethylformamide (DMF), tetrahydrofurane (THF) and dimethylsulfoxide (DMSO). Oligo(BAP) was thermally stable and exhibited 5 % and 50 % mass loss determined by thermogravimetric analysis at 247 degrees C and 852 degrees C, respectively. (c) 2015 Institute of Chemistry, Slovak Academy of Sciences
dc.description.sponsorshipTurkish Ministry of National Education
dc.description.sponsorshipErsen Gokturk would like to acknowledge the Turkish Ministry of National Education for his Ph.D. scholarship.
dc.identifier.doi10.1515/chempap-2015-0242
dc.identifier.endpage619
dc.identifier.issn0366-6352
dc.identifier.issn1336-9075
dc.identifier.issue5
dc.identifier.scopus2-s2.0-84959233655
dc.identifier.scopusqualityQ2
dc.identifier.startpage610
dc.identifier.urihttps://dx.doi.org/10.1515/chempap-2015-0242
dc.identifier.urihttps://hdl.handle.net/11480/3656
dc.identifier.volume70
dc.identifier.wosWOS:000376512000011
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthor[0-Belirlenecek]
dc.language.isoen
dc.publisherSPRINGER INTERNATIONAL PUBLISHING AG
dc.relation.ispartofCHEMICAL PAPERS
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectenzymatic oxidative polymerization
dc.subjecthorseradish peroxidase enzyme
dc.subjectoligophenol
dc.subjecthydrogen peroxide
dc.titleChemoenzymatic polycondensation of para-benzylamino phenol
dc.typeArticle

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