Chemoenzymatic polycondensation of para-benzylamino phenol

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dc.authoridSahmetlioglu, Ertugrul/0000-0002-7324-0385
dc.authoridGokturk, ersen/0000-0001-6742-2847
dc.authoridDemir, Haci Okkes/0000-0002-2078-010X
dc.contributor.authorYildirim, Pinar
dc.contributor.authorGokturk, Ersen
dc.contributor.authorTurac, Ersen
dc.contributor.authorDemir, Haci O.
dc.contributor.authorSahmetlioglu, Ertugrul
dc.date.accessioned2024-09-18T20:19:47Z
dc.date.available2024-09-18T20:19:47Z
dc.date.issued2016
dc.departmentHatay Mustafa Kemal Üniversitesien_US
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 Sciencesen_US
dc.description.sponsorshipTurkish Ministry of National Educationen_US
dc.description.sponsorshipErsen Gokturk would like to acknowledge the Turkish Ministry of National Education for his Ph.D. scholarship.en_US
dc.identifier.doi10.1515/chempap-2015-0242
dc.identifier.endpage619en_US
dc.identifier.issn0366-6352
dc.identifier.issn1336-9075
dc.identifier.issue5en_US
dc.identifier.scopus2-s2.0-84959233655en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage610en_US
dc.identifier.urihttps://doi.org/10.1515/chempap-2015-0242
dc.identifier.urihttps://hdl.handle.net/20.500.12483/9843
dc.identifier.volume70en_US
dc.identifier.wosWOS:000376512000011en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer International Publishing Agen_US
dc.relation.ispartofChemical Papersen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectenzymatic oxidative polymerizationen_US
dc.subjecthorseradish peroxidase enzymeen_US
dc.subjectoligophenolen_US
dc.subjecthydrogen peroxideen_US
dc.titleChemoenzymatic polycondensation of para-benzylamino phenolen_US
dc.typeArticleen_US

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