Linear tetrablock quaterpolymers via triple click reactions, azide-alkyne, diels-alder, and nitroxide radical coupling in a one-pot fashion

Hakan Durmaz; Gurkan Hizal; Umit Tunca

doi:10.1002/pola.24622

Linear tetrablock quaterpolymers via triple click reactions, azide-alkyne, diels-alder, and nitroxide radical coupling in a one-pot fashion

Hakan Durmaz^*, Gurkan Hizal, Umit Tunca

^*Corresponding author for this work

Department of Chemistry

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

48 Citations (Scopus)

Abstract

Azide-alkyne and Diels-Alder click reactions together with a click-like nitroxide radical coupling reaction were used in a one-pot fashion to generate tetrablock quaterpolymer. The various living polymerization generated linear polymers with orthogonal end-functionalities, maleimide-terminated poly(ethylene glycol) (PEG-MI), anthracene- and azide-terminated polystyrene, alkyne- and bromide-terminated poly(tert-butyl acrylate) or alkyne-poly(n-butyl acrylate), and tetramethylpiperidine-1-oxyl (TEMPO)-terminated poly(Îμ- caprolactone) (PCL-TEMPO) were clicked together in a one-pot fashion to generate PEG-b-PS-b-PtBA-b-PCL or PEG-b-PS-b-PnBA-b-PCL quaterpolymer using Cu(0), CuBr, and N,N,Nâ€2,Nâ€3,Nâ€3- pentamethyldiethylenetriamine as catalyst in dimethyl formamide at 80 °C for 36 h. Linear precursors and target quaterpolymers were analyzed via ¹H NMR and gel permeation chromatography.

Original language	English
Pages (from-to)	1962-1968
Number of pages	7
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	49
Issue number	9
DOIs	https://doi.org/10.1002/pola.24622
Publication status	Published - 1 May 2011

Keywords

atom transfer radical polymerization (ATRP)
azide-alkyne cycloaddition reaction
block copolymer
click reactions
Diels-Alder cycloaddition reaction
GPC
nitroxide radical coupling reaction
NMR
poly(ethylene glycol)
poly(Îμ-caprolactone)
poly(n-butyl acrylate)
poly(tert-butyl acrylate)
polystyrene
quaterpolymer
ring opening polymerization (ROP)

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title = "Linear tetrablock quaterpolymers via triple click reactions, azide-alkyne, diels-alder, and nitroxide radical coupling in a one-pot fashion",

abstract = "Azide-alkyne and Diels-Alder click reactions together with a click-like nitroxide radical coupling reaction were used in a one-pot fashion to generate tetrablock quaterpolymer. The various living polymerization generated linear polymers with orthogonal end-functionalities, maleimide-terminated poly(ethylene glycol) (PEG-MI), anthracene- and azide-terminated polystyrene, alkyne- and bromide-terminated poly(tert-butyl acrylate) or alkyne-poly(n-butyl acrylate), and tetramethylpiperidine-1-oxyl (TEMPO)-terminated poly({\^I}μ- caprolactone) (PCL-TEMPO) were clicked together in a one-pot fashion to generate PEG-b-PS-b-PtBA-b-PCL or PEG-b-PS-b-PnBA-b-PCL quaterpolymer using Cu(0), CuBr, and N,N,N{\^a}€2,N{\^a}€3,N{\^a}€3- pentamethyldiethylenetriamine as catalyst in dimethyl formamide at 80 °C for 36 h. Linear precursors and target quaterpolymers were analyzed via 1H NMR and gel permeation chromatography.",

keywords = "atom transfer radical polymerization (ATRP), azide-alkyne cycloaddition reaction, block copolymer, click reactions, Diels-Alder cycloaddition reaction, GPC, nitroxide radical coupling reaction, NMR, poly(ethylene glycol), poly({\^I}μ-caprolactone), poly(n-butyl acrylate), poly(tert-butyl acrylate), polystyrene, quaterpolymer, ring opening polymerization (ROP)",

author = "Hakan Durmaz and Gurkan Hizal and Umit Tunca",

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doi = "10.1002/pola.24622",

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AU - Tunca, Umit

PY - 2011/5/1

Y1 - 2011/5/1

N2 - Azide-alkyne and Diels-Alder click reactions together with a click-like nitroxide radical coupling reaction were used in a one-pot fashion to generate tetrablock quaterpolymer. The various living polymerization generated linear polymers with orthogonal end-functionalities, maleimide-terminated poly(ethylene glycol) (PEG-MI), anthracene- and azide-terminated polystyrene, alkyne- and bromide-terminated poly(tert-butyl acrylate) or alkyne-poly(n-butyl acrylate), and tetramethylpiperidine-1-oxyl (TEMPO)-terminated poly(Îμ- caprolactone) (PCL-TEMPO) were clicked together in a one-pot fashion to generate PEG-b-PS-b-PtBA-b-PCL or PEG-b-PS-b-PnBA-b-PCL quaterpolymer using Cu(0), CuBr, and N,N,Nâ€2,Nâ€3,Nâ€3- pentamethyldiethylenetriamine as catalyst in dimethyl formamide at 80 °C for 36 h. Linear precursors and target quaterpolymers were analyzed via 1H NMR and gel permeation chromatography.

AB - Azide-alkyne and Diels-Alder click reactions together with a click-like nitroxide radical coupling reaction were used in a one-pot fashion to generate tetrablock quaterpolymer. The various living polymerization generated linear polymers with orthogonal end-functionalities, maleimide-terminated poly(ethylene glycol) (PEG-MI), anthracene- and azide-terminated polystyrene, alkyne- and bromide-terminated poly(tert-butyl acrylate) or alkyne-poly(n-butyl acrylate), and tetramethylpiperidine-1-oxyl (TEMPO)-terminated poly(Îμ- caprolactone) (PCL-TEMPO) were clicked together in a one-pot fashion to generate PEG-b-PS-b-PtBA-b-PCL or PEG-b-PS-b-PnBA-b-PCL quaterpolymer using Cu(0), CuBr, and N,N,Nâ€2,Nâ€3,Nâ€3- pentamethyldiethylenetriamine as catalyst in dimethyl formamide at 80 °C for 36 h. Linear precursors and target quaterpolymers were analyzed via 1H NMR and gel permeation chromatography.

KW - atom transfer radical polymerization (ATRP)

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KW - click reactions

KW - Diels-Alder cycloaddition reaction

KW - GPC

KW - nitroxide radical coupling reaction

KW - NMR

KW - poly(ethylene glycol)

KW - poly(Îμ-caprolactone)

KW - poly(n-butyl acrylate)

KW - poly(tert-butyl acrylate)

KW - polystyrene

KW - quaterpolymer

KW - ring opening polymerization (ROP)

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DO - 10.1002/pola.24622

M3 - Article

AN - SCOPUS:79953044504

SN - 0887-624X

VL - 49

SP - 1962

EP - 1968

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 9

ER -

Linear tetrablock quaterpolymers via triple click reactions, azide-alkyne, diels-alder, and nitroxide radical coupling in a one-pot fashion

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Keywords

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