1,3-Dipolar and Diels–Alder cycloaddition reactions on polyester backbones possessing internal electron-deficient alkyne moieties

Cetin, Muge; Esen, Cansu; Dağlar, Özgün; Luleburgaz, Serter; Hızal, Gürkan; Durmaz, Hakan; Tunca, Ümit

doi:10.1039/c6py01827k

Cited by 42 publications

(44 citation statements)

References 37 publications

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“…Octakis azido‐POSS (POSS‐N 3 as viscous liquid) was prepared according to the literature . The poly(1,4‐cyclohexanedimethylene acetylene dicarboxylate) (PCA) was synthesized according to our published procedure . Tetrahydrofuran (THF, %99, Merck) was used without any purification.…”

Section: Methodsmentioning

confidence: 99%

“…The strain‐promoted azide‐alkyne cycloaddition reaction between azides and strained alkynes, was developed by Bertozzi and coworkers, is widely applied for bioconjugation of live organisms. Recently, Tang and coworkers, Schubert et al, and Durmaz and coworkers groups have developed alternative copper‐free 1,3‐dipolar cycloaddition reactions between azides and electron‐deficient alkynes under mild conditions. The key of this click reaction is that the usage of adjacent electron‐withdrawing functional group makes the alkynes very electron deficient and suitable for cycloaddition reaction with azide to produce a triazole at room temperature under mild reaction conditions without using a metal catalyst.…”

Section: Introductionmentioning

confidence: 99%

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Aliphatic Polyester/polyhedral Oligomeric Silsesquioxanes Hybrid Networks via Copper‐free 1,3‐dipolar Cycloaddition Click Reaction

Özdoğan

Dağlar

Durmaz

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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In this study, we describe the preparation and characterization of a new class of thermoset hybrid networks containing aliphatic polyester and polyhedral oligomeric silsesquioxanes (POSS). The copper‐free 1,3‐dipolar cycloaddition click reaction of internal alkyne functionalized aliphatic polyester and multifunctional azido POSS with different concentrations led to highly crosslinked thermoset networks. The click reactions performed under ambient conditions (i.e., in tetrahydrofuran at room temperature for 1 day) in the absence of any catalyst. The chemical composition of hybrid networks and homogenous distribution of POSS molecules were confirmed by Fourier transform infrared spectroscopy and scanning electron microscopy with energy dispersive spectroscopy. The swelling ratios of hybrid networks were commonly decreased by increasing POSS‐N3 content and by changing polar solvents to apolar solvents. Thermogravimetric analysis results demonstrated that the thermal stability of hybrid networks increased with higher POSS feeding ratio. Tensile tests were applied to evaluate the mechanical properties of hybrid networks. Compared to neat aliphatic polyester, the mechanical properties of hybrid networks significantly improved. For instance, the tensile strength were enhanced from 5 MPa to 19 MPa by increasing the concentration of azido functionalized POSS from 10 to 40. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2222–2227

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Aliphatic Polyester/polyhedral Oligomeric Silsesquioxanes Hybrid Networks via Copper‐free 1,3‐dipolar Cycloaddition Click Reaction

Özdoğan

Dağlar

Durmaz

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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“…However, the strained cycloalkyne derivatives to be employed in the SPAAC require expensive reagents and too many synthetic steps. Recently, electron deficient alkyne units were simply incorporated into the polymer chain and subsequently employed in cycloaddition reactions (AAC and Diels–Alder) for orthogonal functionalization at comparatively low temperatures …”

Section: Introductionmentioning

confidence: 99%

Click and Multicomponent Reactions Work Together for Polymer Chemistry

Tunca

2018

Macro Chemistry & Physics

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This article investigates the current combinations of click and multicomponent reactions (MCRs) to produce complex macromolecular structures through polymer–polymer conjugation or hetero‐functionalization of polymers. The click and MCRs display similar features covering the equimolarity, fast time scale, high yields, stable compounds, modular, orthogonal and single reaction trajectory. Of classical click reactions, CuAAC, Diels–Alder, thiol‐ene (‐yne), and nucleophilic substitution on perfluoroaryl groups reactions are combined with MCRs, namely, Passerini, Ugi, or Biginelli reactions. It should be noted that these combinations can afford the target polymer structures, which are not attainable by employing one of these reactions alone.

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“…Thiol‐based reactions such as thiol‐ene/yne, thiol‐Michael addition, and thiol‐epoxy reactions have been well‐known and well‐studied in the literature . Moreover, these reactions are also classified under the term “click” chemistry as the mild reaction conditions along with high yields and efficiencies, which are the basic requirements of “click” reactions, are mostly observed when these reactions are utilized. Besides, in the last decade, another thiol‐based reaction namely, para ‐fluoro‐thiol reaction (PFTR), has gained much interest and made a significant contribution especially on synthetic polymer chemistry .…”

Section: Introductionmentioning

confidence: 99%

Preparation of linear and hyperbranched fluorinated poly(aryl ether‐thioether) through para‐fluoro‐thiol click reaction

Baysak

Tunca

Hızal

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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The para‐fluoro‐thiol “click” reaction (PFTCR) was utilized to prepare linear and hyperbranched fluorinated poly (aryl ether‐thioether). For this purpose, 1,2‐bis(perfluorophenoxy)ethane was prepared and reacted with 1,6‐hexandithiol and trimethylolpropane tris(3‐mercaptopropionate), respectively. While hyperbranched polymers were prepared using 0.5 M concentrations of starting materials at room temperature, the linear polymer syntheses were performed at different reaction temperatures and concentrations. The resulting polymers were mainly characterized by NMR measurements and a very distinct fluorine signals regarding meta‐ and ortho‐ positions in the 19F NMR were found for both polymer topologies. In addition to NMR analyses, both linear and hyperbranched polymers were further characterized by using Fourier transform infrared spectroscopy (FT‐IR), gel permeation chromatography (GPC), and differential scanning calorimetry (DSC). © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1853–1859

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1,3-Dipolar and Diels–Alder cycloaddition reactions on polyester backbones possessing internal electron-deficient alkyne moieties

Abstract: A polyester containing electron deficient internal alkyne units derived from acetylene dicarboxylic acid in the main backbone was employed as a polymeric platform in copper free cycloaddition reactions.

Cited by 42 publications

References 37 publications

Aliphatic Polyester/polyhedral Oligomeric Silsesquioxanes Hybrid Networks via Copper‐free 1,3‐dipolar Cycloaddition Click Reaction

Aliphatic Polyester/polyhedral Oligomeric Silsesquioxanes Hybrid Networks via Copper‐free 1,3‐dipolar Cycloaddition Click Reaction

Click and Multicomponent Reactions Work Together for Polymer Chemistry

Preparation of linear and hyperbranched fluorinated poly(aryl ether‐thioether) through para‐fluoro‐thiol click reaction

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