Quantitative ω-amination, ω-azidolysis, and ω-thiolation of poly(ethylene oxide)s through anionic mechanism

Sung Woo Kim; Abu Bakkar Siddique; Jin Wook An; Hyeon Jong Park; Hyun Jun Kim; Ho Jung Kang; Jae Yeol Lee; Sehoon Kim; Jungahn Kim

doi:10.1007/s13233-016-4023-7

Quantitative ω-amination, ω-azidolysis, and ω-thiolation of poly(ethylene oxide)s through anionic mechanism

Sung Woo Kim, Abu Bakkar Siddique, Jin Wook An, Hyeon Jong Park, Hyun Jun Kim, Ho Jung Kang, Jae Yeol Lee, Sehoon Kim, Jungahn Kim

KU-KIST Graduate School of Converging Science and Technology

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

3 Citations (Scopus)

Abstract

n-Butyllithium-initiated ring-opening polymerization of ethylene oxide with potassium t-butoxide in the mixture of benzene and dimethyl sulfoxide (DMSO) at 35 °C yielded corresponding “living” polymeric alkoxide. The molecular weight was well controlled on the basis of stoichiometric balance. Quantitative chain-end functionalizations, such as the amination, the azidation, and the thiolation of polymeric alkoxide, were performed. The yields were almost quantitative (over 98 mol%). The resulting products were characterized by the combination of ¹H NMR spectroscopy, UV/Visible spectroscopy, FTIR, MALDI-TOF MS analysis, and size exclusion chromatographic analysis.[Figure not available: see fulltext.]

Original language	English
Pages (from-to)	188-195
Number of pages	8
Journal	Macromolecular Research
Volume	24
Issue number	2
DOIs	https://doi.org/10.1007/s13233-016-4023-7
Publication status	Published - 2016 Feb 1

Keywords

amination
azidation
chain-end functionalizations
molecular weight control
poly(ethylene oxide)
thiolation

ASJC Scopus subject areas

Chemical Engineering(all)
Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1007/s13233-016-4023-7

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title = "Quantitative ω-amination, ω-azidolysis, and ω-thiolation of poly(ethylene oxide)s through anionic mechanism",

abstract = "n-Butyllithium-initiated ring-opening polymerization of ethylene oxide with potassium t-butoxide in the mixture of benzene and dimethyl sulfoxide (DMSO) at 35 °C yielded corresponding “living” polymeric alkoxide. The molecular weight was well controlled on the basis of stoichiometric balance. Quantitative chain-end functionalizations, such as the amination, the azidation, and the thiolation of polymeric alkoxide, were performed. The yields were almost quantitative (over 98 mol%). The resulting products were characterized by the combination of 1H NMR spectroscopy, UV/Visible spectroscopy, FTIR, MALDI-TOF MS analysis, and size exclusion chromatographic analysis.[Figure not available: see fulltext.]",

keywords = "amination, azidation, chain-end functionalizations, molecular weight control, poly(ethylene oxide), thiolation",

author = "Kim, {Sung Woo} and Siddique, {Abu Bakkar} and An, {Jin Wook} and Park, {Hyeon Jong} and Kim, {Hyun Jun} and Kang, {Ho Jung} and Lee, {Jae Yeol} and Sehoon Kim and Jungahn Kim",

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doi = "10.1007/s13233-016-4023-7",

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T1 - Quantitative ω-amination, ω-azidolysis, and ω-thiolation of poly(ethylene oxide)s through anionic mechanism

AU - Kim, Sung Woo

AU - Siddique, Abu Bakkar

AU - An, Jin Wook

AU - Park, Hyeon Jong

AU - Kim, Hyun Jun

AU - Kang, Ho Jung

AU - Lee, Jae Yeol

AU - Kim, Sehoon

AU - Kim, Jungahn

PY - 2016/2/1

Y1 - 2016/2/1

N2 - n-Butyllithium-initiated ring-opening polymerization of ethylene oxide with potassium t-butoxide in the mixture of benzene and dimethyl sulfoxide (DMSO) at 35 °C yielded corresponding “living” polymeric alkoxide. The molecular weight was well controlled on the basis of stoichiometric balance. Quantitative chain-end functionalizations, such as the amination, the azidation, and the thiolation of polymeric alkoxide, were performed. The yields were almost quantitative (over 98 mol%). The resulting products were characterized by the combination of 1H NMR spectroscopy, UV/Visible spectroscopy, FTIR, MALDI-TOF MS analysis, and size exclusion chromatographic analysis.[Figure not available: see fulltext.]

AB - n-Butyllithium-initiated ring-opening polymerization of ethylene oxide with potassium t-butoxide in the mixture of benzene and dimethyl sulfoxide (DMSO) at 35 °C yielded corresponding “living” polymeric alkoxide. The molecular weight was well controlled on the basis of stoichiometric balance. Quantitative chain-end functionalizations, such as the amination, the azidation, and the thiolation of polymeric alkoxide, were performed. The yields were almost quantitative (over 98 mol%). The resulting products were characterized by the combination of 1H NMR spectroscopy, UV/Visible spectroscopy, FTIR, MALDI-TOF MS analysis, and size exclusion chromatographic analysis.[Figure not available: see fulltext.]

KW - amination

KW - azidation

KW - chain-end functionalizations

KW - molecular weight control

KW - poly(ethylene oxide)

KW - thiolation

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DO - 10.1007/s13233-016-4023-7

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SN - 1598-5032

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SP - 188

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JO - Macromolecular Research

JF - Macromolecular Research

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ER -

Quantitative ω-amination, ω-azidolysis, and ω-thiolation of poly(ethylene oxide)s through anionic mechanism

Abstract

Keywords

ASJC Scopus subject areas

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