Diels-alder click reaction for the preparation of polycarbonate block copolymers

Pinar Sinem Omurtag; Ufuk Saim Gunay; Aydan Dag; Hakan Durmaz; Gurkan Hizal; Umit Tunca

doi:10.1002/pola.26608

Diels-alder click reaction for the preparation of polycarbonate block copolymers

Pinar Sinem Omurtag, Ufuk Saim Gunay, Aydan Dag, Hakan Durmaz, Gurkan Hizal, Umit Tunca^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

14 Citations (Scopus)

Abstract

The Diels-Alder reaction as a click reaction strategy is applied to the preparation of well-defined polycarbonate (PC)-block copolymers. A well-defined α-anthracene-terminated polycarbonate (PC-anthracene) is prepared using 9-anthracene methanol as an initiator in the ring opening polymerization of benzyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate in CH₂Cl₂ at room temperature for 5 h. Next, a well-defined α-furan protected maleimide-terminated-poly(ethylene glycol) (PEG₁₁-MI or PEG ₃₇-MI), -poly(methyl methacrylate) (PMMA₂₆-MI), and -poly(ε-caprolactone) (PCL₂₇-MI) were clicked with the PC-anthracene at reflux temperature of toluene to yield their corresponding PC-based block copolymers (PC-b-PEG, PC-b-PMMA, and PC-b-PCL). The homopolymer precursors and their block copolymers were characterized by using the GPC, NMR and UV analysis.

Original language	English
Pages (from-to)	2252-2259
Number of pages	8
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	51
Issue number	10
DOIs	https://doi.org/10.1002/pola.26608
Publication status	Published - 15 May 2013

Keywords

Diels-Alder click reaction
H NMR spectroscopy
aliphatic polycarbonate (PC)
anthracene terminated polycarbonate
block copolymer
click reactions
gel permeation chromatography (GPC)
maleimide-terminated poly(ethylene glycol)
maleimide-terminated poly(methyl methacrylate)
maleimide-terminated poly(ε-caprolactone)

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10.1002/pola.26608

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title = "Diels-alder click reaction for the preparation of polycarbonate block copolymers",

abstract = "The Diels-Alder reaction as a click reaction strategy is applied to the preparation of well-defined polycarbonate (PC)-block copolymers. A well-defined α-anthracene-terminated polycarbonate (PC-anthracene) is prepared using 9-anthracene methanol as an initiator in the ring opening polymerization of benzyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate in CH2Cl2 at room temperature for 5 h. Next, a well-defined α-furan protected maleimide-terminated-poly(ethylene glycol) (PEG11-MI or PEG 37-MI), -poly(methyl methacrylate) (PMMA26-MI), and -poly(ε-caprolactone) (PCL27-MI) were clicked with the PC-anthracene at reflux temperature of toluene to yield their corresponding PC-based block copolymers (PC-b-PEG, PC-b-PMMA, and PC-b-PCL). The homopolymer precursors and their block copolymers were characterized by using the GPC, NMR and UV analysis.",

keywords = "Diels-Alder click reaction, H NMR spectroscopy, aliphatic polycarbonate (PC), anthracene terminated polycarbonate, block copolymer, click reactions, gel permeation chromatography (GPC), maleimide-terminated poly(ethylene glycol), maleimide-terminated poly(methyl methacrylate), maleimide-terminated poly(ε-caprolactone)",

author = "Omurtag, {Pinar Sinem} and Gunay, {Ufuk Saim} and Aydan Dag and Hakan Durmaz and Gurkan Hizal and Umit Tunca",

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AU - Omurtag, Pinar Sinem

AU - Gunay, Ufuk Saim

AU - Dag, Aydan

AU - Durmaz, Hakan

AU - Hizal, Gurkan

AU - Tunca, Umit

PY - 2013/5/15

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N2 - The Diels-Alder reaction as a click reaction strategy is applied to the preparation of well-defined polycarbonate (PC)-block copolymers. A well-defined α-anthracene-terminated polycarbonate (PC-anthracene) is prepared using 9-anthracene methanol as an initiator in the ring opening polymerization of benzyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate in CH2Cl2 at room temperature for 5 h. Next, a well-defined α-furan protected maleimide-terminated-poly(ethylene glycol) (PEG11-MI or PEG 37-MI), -poly(methyl methacrylate) (PMMA26-MI), and -poly(ε-caprolactone) (PCL27-MI) were clicked with the PC-anthracene at reflux temperature of toluene to yield their corresponding PC-based block copolymers (PC-b-PEG, PC-b-PMMA, and PC-b-PCL). The homopolymer precursors and their block copolymers were characterized by using the GPC, NMR and UV analysis.

AB - The Diels-Alder reaction as a click reaction strategy is applied to the preparation of well-defined polycarbonate (PC)-block copolymers. A well-defined α-anthracene-terminated polycarbonate (PC-anthracene) is prepared using 9-anthracene methanol as an initiator in the ring opening polymerization of benzyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate in CH2Cl2 at room temperature for 5 h. Next, a well-defined α-furan protected maleimide-terminated-poly(ethylene glycol) (PEG11-MI or PEG 37-MI), -poly(methyl methacrylate) (PMMA26-MI), and -poly(ε-caprolactone) (PCL27-MI) were clicked with the PC-anthracene at reflux temperature of toluene to yield their corresponding PC-based block copolymers (PC-b-PEG, PC-b-PMMA, and PC-b-PCL). The homopolymer precursors and their block copolymers were characterized by using the GPC, NMR and UV analysis.

KW - Diels-Alder click reaction

KW - H NMR spectroscopy

KW - aliphatic polycarbonate (PC)

KW - anthracene terminated polycarbonate

KW - block copolymer

KW - click reactions

KW - gel permeation chromatography (GPC)

KW - maleimide-terminated poly(ethylene glycol)

KW - maleimide-terminated poly(methyl methacrylate)

KW - maleimide-terminated poly(ε-caprolactone)

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

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Diels-alder click reaction for the preparation of polycarbonate block copolymers

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