Post modification of acetylene functional poly(oxindole biphenylylene) by photoinduced CuAAC

Mustafa Arslan, Tugrul Cem Bicak, Bruno A. Pulido, Suzana P. Nunes*, Yusuf Yagci

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)298-307
Number of pages10
JournalEuropean Polymer Journal
Volume100
DOIs
StatePublished - Mar 2018

Bibliographical note

Funding Information:
The authors would like to thank Istanbul Technical University, Research Fund, and King Abdullah University of Science and Technology (KAUST) for financial support.

Publisher Copyright:
© 2018 Elsevier Ltd

Keywords

  • Grafting
  • Photo-induced CuAAC
  • Poly(ethylene glycol)
  • Poly(oxindolebiphenylylene)
  • Pyrene

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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