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

M. Arslan, T.C. Bicak, B. Pulido, S.P. Nunes, Y. Yagci
European Polymer Journal, (2018)

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

Keywords

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

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.

Code

DOI: 10.1016/j.eurpolymj.2018.02.009

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