Post Modification of Acetylene Functional Poly(oxindole biphenylylene) by Photoinduced CuAAC

Handle URI:
http://hdl.handle.net/10754/627125
Title:
Post Modification of Acetylene Functional Poly(oxindole biphenylylene) by Photoinduced CuAAC
Authors:
Arslan, Mustafa; Cem Bicak, Tugrul; Pulido, Bruno; Nunes, Suzana Pereira ( 0000-0002-3669-138X ) ; Yagci, Yusuf
Abstract:
A novel strategy to obtain side chain modified poly(oxindole biphenylylene) (POXI) by photoinduced copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction is described. In the first step, an alkyne-functionalized poly(oxindolebiphenylylene) (POXI-alkyne) is synthesized by superacid-catalyzed condensation of isatin with aromatic hydrocarbons. Subsequently, poly(ethylene glycol) methyl ether (Me-PEG), 1-pyrenemethanol (Py-OH) and 1,3-dibromopropane (DBP) are functionalized by azide groups via simple nucleophilic substitution reaction. Visible-light-induced CuAAC reaction between POXI-alkyne and the corresponding azide functionalized click components employing dibenzoyldiethylgermane (DBDEG) as photoactivator resulted in the formation of POXI-PEG, POXI-Py and insoluble network, respectively. Successful modification of POXI was confirmed by the spectral, (1H NMR, FT-IR, Fluorescence), chromatographic (GPC) and thermal (DSC) investigations.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; Environmental Science and Engineering Program
Citation:
Arslan M, Cem Bicak T, Pulido B, Nunes SP, Yagci Y (2018) Post Modification of Acetylene Functional Poly(oxindole biphenylylene) by Photoinduced CuAAC. European Polymer Journal. Available: http://dx.doi.org/10.1016/j.eurpolymj.2018.02.009.
Publisher:
Elsevier BV
Journal:
European Polymer Journal
Issue Date:
8-Feb-2018
DOI:
10.1016/j.eurpolymj.2018.02.009
Type:
Article
ISSN:
0014-3057
Sponsors:
The authors would like to thank Istanbul Technical University, Research Fund, and King Abdullah University of Science and Technology (KAUST) for financial support.
Additional Links:
https://www.sciencedirect.com/science/article/pii/S001430571732013X
Appears in Collections:
Articles; Environmental Science and Engineering Program; Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorArslan, Mustafaen
dc.contributor.authorCem Bicak, Tugrulen
dc.contributor.authorPulido, Brunoen
dc.contributor.authorNunes, Suzana Pereiraen
dc.contributor.authorYagci, Yusufen
dc.date.accessioned2018-02-13T13:43:19Z-
dc.date.available2018-02-13T13:43:19Z-
dc.date.issued2018-02-08en
dc.identifier.citationArslan M, Cem Bicak T, Pulido B, Nunes SP, Yagci Y (2018) Post Modification of Acetylene Functional Poly(oxindole biphenylylene) by Photoinduced CuAAC. European Polymer Journal. Available: http://dx.doi.org/10.1016/j.eurpolymj.2018.02.009.en
dc.identifier.issn0014-3057en
dc.identifier.doi10.1016/j.eurpolymj.2018.02.009en
dc.identifier.urihttp://hdl.handle.net/10754/627125-
dc.description.abstractA novel strategy to obtain side chain modified poly(oxindole biphenylylene) (POXI) by photoinduced copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction is described. In the first step, an alkyne-functionalized poly(oxindolebiphenylylene) (POXI-alkyne) is synthesized by superacid-catalyzed condensation of isatin with aromatic hydrocarbons. Subsequently, poly(ethylene glycol) methyl ether (Me-PEG), 1-pyrenemethanol (Py-OH) and 1,3-dibromopropane (DBP) are functionalized by azide groups via simple nucleophilic substitution reaction. Visible-light-induced CuAAC reaction between POXI-alkyne and the corresponding azide functionalized click components employing dibenzoyldiethylgermane (DBDEG) as photoactivator resulted in the formation of POXI-PEG, POXI-Py and insoluble network, respectively. Successful modification of POXI was confirmed by the spectral, (1H NMR, FT-IR, Fluorescence), chromatographic (GPC) and thermal (DSC) investigations.en
dc.description.sponsorshipThe authors would like to thank Istanbul Technical University, Research Fund, and King Abdullah University of Science and Technology (KAUST) for financial support.en
dc.publisherElsevier BVen
dc.relation.urlhttps://www.sciencedirect.com/science/article/pii/S001430571732013Xen
dc.rightsNOTICE: this is the author’s version of a work that was accepted for publication in European Polymer Journal. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in European Polymer Journal, [, , (2018-02-08)] DOI: 10.1016/j.eurpolymj.2018.02.009 . © 2018. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subjectPhoto-induced CuAACen
dc.subjectgraftingen
dc.subjectpoly(oxindolebiphenylylene)en
dc.subjectpoly(ethylene glycolen
dc.subjectpyreneen
dc.titlePost Modification of Acetylene Functional Poly(oxindole biphenylylene) by Photoinduced CuAACen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentEnvironmental Science and Engineering Programen
dc.identifier.journalEuropean Polymer Journalen
dc.eprint.versionPost-printen
dc.contributor.institutionKirklareli University, Faculty of Science and Letters, Department of Chemistry, 39000, Kirklareli, Turkeyen
dc.contributor.institutionIstanbul Technical University, Faculty of Science and Letters, Department of Chemistry, Maslak, 34469, Istanbul, Turkeyen
kaust.authorPulido, Brunoen
kaust.authorNunes, Suzana Pereiraen
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.