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

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

doi:10.1016/j.eurpolymj.2018.02.009

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

Biological, Environmental Sciences and Engineering

Research output: Contribution to journal › Article › peer-review

10 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 language	English (US)
Pages (from-to)	298-307
Number of pages	10
Journal	European Polymer Journal
Volume	100
DOIs	https://doi.org/10.1016/j.eurpolymj.2018.02.009
State	Published - Mar 2018

Bibliographical note

Publisher Copyright:
© 2018 Elsevier Ltd

Keywords

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

ASJC Scopus subject areas

General Physics and Astronomy
Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1016/j.eurpolymj.2018.02.009

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title = "Post modification of acetylene functional poly(oxindole biphenylylene) by photoinduced CuAAC",

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.",

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

author = "Mustafa Arslan and Bicak, {Tugrul Cem} and Pulido, {Bruno A.} and Nunes, {Suzana P.} and Yusuf Yagci",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = mar,

doi = "10.1016/j.eurpolymj.2018.02.009",

language = "English (US)",

volume = "100",

pages = "298--307",

journal = "European Polymer Journal",

issn = "0014-3057",

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TY - JOUR

T1 - Post modification of acetylene functional poly(oxindole biphenylylene) by photoinduced CuAAC

AU - Arslan, Mustafa

AU - Bicak, Tugrul Cem

AU - Pulido, Bruno A.

AU - Nunes, Suzana P.

AU - Yagci, Yusuf

PY - 2018/3

Y1 - 2018/3

N2 - 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.

AB - 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.

KW - Grafting

KW - Photo-induced CuAAC

KW - Poly(ethylene glycol)

KW - Poly(oxindolebiphenylylene)

KW - Pyrene

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DO - 10.1016/j.eurpolymj.2018.02.009

M3 - Article

AN - SCOPUS:85041909752

SN - 0014-3057

VL - 100

SP - 298

EP - 307

JO - European Polymer Journal

JF - European Polymer Journal

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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