Synthesis of Terpolymers by Click Reactions

Altintas, Ozcan; Tunca, Ümit

doi:10.1002/asia.201100138

Cited by 71 publications

(36 citation statements)

References 57 publications

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“…ATRP, ROP, NMP or RAFT and consecutive reactions such as, copper catalyzed alkyne‐azide reaction, Diels‐Alder reaction, thiol‐ene reaction, etc. have been exploited for the precise and modular synthesis of various macromolecular architectures by taking advantages offered by these techniques …”

Section: Introductionmentioning

confidence: 99%

A convenient synthesis of α,α′‐ homo‐ and α,α′‐hetero‐bifunctionalized poly(ε‐caprolactone)s by ring opening polymerization: The potentially valuable precursors for miktoarm star copolymers

Patil

Tawade

Wadgaonkar

2015

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

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Two new ring opening polymerization (ROP) initiators, namely, (3‐allyl‐2‐(allyloxy)phenyl)methanol and (3‐allyl‐2‐(prop‐2‐yn‐1‐yloxy)phenyl)methanol each containing two reactive functionalities viz. allyl, allyloxy and allyl, propargyloxy, respectively, were synthesized from 3‐allylsalicyaldehyde as a starting material. Well defined α‐allyl, α′‐allyloxy and α‐allyl, α′‐propargyloxy bifunctionalized poly(ε‐caprolactone)s with molecular weights in the range 4200–9500 and 3600–10,900 g/mol and molecular weight distributions in the range 1.16–1.18 and 1.15–1.16, respectively, were synthesized by ROP of ε‐caprolactone employing these initiators. The presence of α‐allyl, α′‐allyloxy and α‐allyl, α′‐propargyloxy functionalities on poly(ε‐caprolactone)s was confirmed by FT‐IR, 1H, 13C NMR spectroscopy, and MALDI‐TOF analysis. The kinetic study of ROP of ε‐caprolactone with both the initiators revealed the pseudo first order kinetics with respect to ε‐caprolactone consumption and controlled behavior of polymerization reactions. The usefulness of α‐allyl, α′‐allyloxy functionalities on poly(ε‐caprolactone) was demonstrated by performing the thiol‐ene reaction with poly(ethylene glycol) thiol to obtain (mPEG)2‐PCL miktoarm star copolymer. α‐Allyl, α′‐propargyloxy functionalities on poly(ε‐caprolactone) were utilized in orthogonal reactions i.e copper catalyzed alkyne‐azide click (CuAAC) with azido functionalized poly(N‐isopropylacrylamide) followed by thiol‐ene reaction with poly(ethylene glycol) thiol to synthesize PCL‐PNIPAAm‐mPEG miktoarm star terpolymer. The preliminary characterization of A2B and ABC miktoarm star copolymers was carried out by 1H NMR spectroscopy and gel permeation chromatography (GPC). © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 844–860

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Section: Introductionmentioning

confidence: 99%

A convenient synthesis of α,α′‐ homo‐ and α,α′‐hetero‐bifunctionalized poly(ε‐caprolactone)s by ring opening polymerization: The potentially valuable precursors for miktoarm star copolymers

Patil

Tawade

Wadgaonkar

2015

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

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“…Later, the same group extended the method to quadruple click reactions including thiol‐ene for the preparation of cysteine‐terminated linear PS‐ b ‐PCL‐ b ‐PMMA‐ b ‐PEG copolymers . Other interesting examples of multiblock linear copolymers obtained with this strategy have also been reported …”

Section: Development Of Novel Macromolecular Architectures By Nrc Reamentioning

confidence: 99%

“…13,141,146,147 Other interesting examples of multiblock linear copolymers obtained with this strategy have also been reported. [148][149][150] Furthermore, ATNRC and SETNRC have been used to synthesize graft copolymers. Huang and colleagues prepared a series of heterograft copolymers using the linear precursor poly(4glycidyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl-co-ethylene oxide) (poly(GTEMPO-co-EO)) bearing multi-pendent TEMPO moieties, PS-Br or PtBA-Br with a bromide end group and by adding CuBr/PMDETA at 90 ∘ C. 151,152 Combining CuAAC chemistry with the NRC reaction, Huang and coworkers synthesized also an ABA type block-graft copolymer between a backbone with pendent TEMPO and azide groups and PtBA-Br and PS-alkyne precursors in a one-pot style.…”

Section: Atnrc and Setnrc Reactions For Polymer-polymer Conjugationmentioning

confidence: 99%

Post‐polymerization modification by nitroxide radical coupling

Coiai

Passaglia

Cicogna

2018

Polymer International

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Post‐polymerization modification is an attractive approach to extend applications and convert commodity plastics into products with new, desirable and tunable properties. Among the post‐polymerization modification methods, the nitroxide radical coupling (NRC) reaction has been shown to be a convenient and versatile way to graft specific functionalities onto polymer chains and to control the onset and yield of polymer crosslinking during peroxide‐initiated processes. The use of 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) and its derivatives as controllers of scorch in crosslinking and as functionalizers in functionalization reactions is thoroughly described. Examples are also given of graft polymerization from macroalkoxyamines generated by NRC and grafting of nitroxides by irradiation processes. In addition, in this review we attempt to demonstrate the broad applications of the NRC reaction in the preparation of polymers with a multitude of functionalities and elaborate architectures. The examples discussed here concern the use of atom transfer and single electron transfer NRC reactions to design a variety of polymers with asymmetrical structure and the use of the radical crossover reaction, based on the alkoxyamine dynamic covalent bond, to generate reversible polymer structures and switchable functional polymers. © 2018 Society of Chemical Industry

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“…The most popular click reactions are copper‐catalyzed azide–alkyne cycloaddition (CuAAC), Diels–Alder cycloaddition, thiol‐ene, thiol‐yne, and nitroxide radical coupling (NRC). These reactions have just been adapted toward modular construction approach in the preparative polymer chemistry and opened up a particularly rapid, efficient, and mild reaction routes to the preparation of a specific polymer structure …”

Section: Introductionmentioning

confidence: 99%

V-shaped graft copolymers via triple click reactions: Diels-alder, copper-catalyzed azide-alkyne cycloaddition, and nitroxide radical coupling

Gunay

Özsoy

Durmaz

et al. 2013

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

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We report here a simple and universal synthetic pathway covering triple click reactions, Diels–Alder, copper‐catalyzed azide–alkyne cycloaddition (CuAAC), and nitroxide radical coupling (NRC), to prepare well‐defined graft copolymers with V‐shaped side chains. The Diels–Alder click reaction between the furan protected‐maleimide‐terminated poly(ethylene glycol) (PEG) and a trifunctional core (1) carrying an anthracene, alkyne, and bromide was carried out to yield the corresponding α‐alkyne‐ and α‐bromide‐terminated PEG (PEG‐alkyne/Br) in toluene at 110 °C. Subsequently, the polystyrene or polyoxanorbornene with pendant azide functionality as a main backbone is reacted with the PEG‐alkyne/Br and 2,2,6,6‐tetramethyl‐1‐piperidinyloxy (TEMPO)‐terminated poly(ε‐caprolactone) using the CuAAC and NRC reactions in a one‐pot fashion in N,N′‐dimethylformamide at room temperature to result in the target V‐shaped graft copolymers. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4667–4674

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Synthesis of Terpolymers by Click Reactions

Cited by 71 publications

References 57 publications

A convenient synthesis of α,α′‐ homo‐ and α,α′‐hetero‐bifunctionalized poly(ε‐caprolactone)s by ring opening polymerization: The potentially valuable precursors for miktoarm star copolymers

A convenient synthesis of α,α′‐ homo‐ and α,α′‐hetero‐bifunctionalized poly(ε‐caprolactone)s by ring opening polymerization: The potentially valuable precursors for miktoarm star copolymers

Post‐polymerization modification by nitroxide radical coupling

V-shaped graft copolymers via triple click reactions: Diels-alder, copper-catalyzed azide-alkyne cycloaddition, and nitroxide radical coupling

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