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Post Modification of Acetylene Functional Poly(oxindole biphenylylene) by Photoinduced CuAAC
European Polymer Journal ( IF 6 ) Pub Date : 2018-03-01 , DOI: 10.1016/j.eurpolymj.2018.02.009
Mustafa Arslan , Tugrul Cem Bicak , Bruno A. Pulido , Suzana P. Nunes , Yusuf Yagci

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.

中文翻译:

光致CuAAC对乙炔官能聚(羟吲哚联苯)的后改性

摘要 描述了一种通过光诱导铜 (I) 催化叠氮化物-炔环加成 (CuAAC) 点击反应获得侧链改性聚(羟吲哚亚联苯)(POXI)的新策略。在第一步中,通过靛红与芳烃的超强酸催化缩合合成炔官能化的聚(oxindolebiphenylylene)(POXI-炔烃)。随后,聚(乙二醇)甲基醚(Me-PEG)、1-芘甲醇(Py-OH)和1,3-二溴丙烷(DBP)通过简单的亲核取代反应被叠氮基团官能化。可见光诱导的 POXI-炔烃与相应的叠氮化物功能化点击组分(采用二苯甲酰二乙基锗烷(DBDEG)作为光活化剂)之间的 CuAAC 反应分别导致 POXI-PEG、POXI-Py 和不溶性网络的形成。
更新日期:2018-03-01
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