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

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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.

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Authors and Affiliations

  1. Department of Chemistry, Kyung Hee University, Seoul, 02453, Korea

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

  2. Center for Theranostics, KIST, Seoul, 02792, Korea

    Sehoon Kim

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  1. Sung Woo Kim
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  2. Abu Bakkar Siddique
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  3. Jin Wook An
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  4. Hyeon Jong Park
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  5. Hyun Jun Kim
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  9. Jungahn Kim
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Correspondence to Jungahn Kim.

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Kim, S.W., Siddique, A.B., An, J.W. et al. Quantitative ω-amination, ω-azidolysis, and ω-thiolation of poly(ethylene oxide)s through anionic mechanism. Macromol. Res. 24, 188–195 (2016). https://doi.org/10.1007/s13233-016-4023-7

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  • DOI: https://doi.org/10.1007/s13233-016-4023-7

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