Azide-based heterobifunctional poly(ethylene oxide)s: NaN3-initiated "living" polymerization of ethylene oxide and chain end functionalizations

Sera Yang; Youn Kim; Hyeong Cheol Kim; Abu B. Siddique; Gyusaang Youn; Hyun Jun Kim; Hyeon Jong Park; Jae Yeol Lee; Sehoon Kim; Jungahn Kim

doi:10.1039/c5py01444a

Azide-based heterobifunctional poly(ethylene oxide)s: NaN₃-initiated "living" polymerization of ethylene oxide and chain end functionalizations

Sera Yang, Youn Kim, Hyeong Cheol Kim, Abu B. Siddique, Gyusaang Youn, Hyun Jun Kim, Hyeon Jong Park, Jae Yeol Lee, Sehoon Kim, Jungahn Kim

KU-KIST Graduate School of Converging Science and Technology

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

7 Citations (Scopus)

Abstract

In this study, sodium azide (NaN₃) was employed as a functional anionic initiator to polymerize ethylene oxide in N,N-dimethylformamide (DMF) leading to the production of the reactive polymeric alkoxide. The molecular weights of all products were controlled within the 2800-10-000 g mol^-1 range on the basis of the stoichiometric balance. NaN₃-initiated polymerization of ethylene oxide (EO) and chain end functionalization of the resulting alkoxide were found to be a simple and efficient method for synthesizing heterobifunctional PEOs. The reaction route via chain end tosylation of α-azide PEOs was found to yield almost quantitative functionalizations for the synthesis of α-azide-ω-tosyl PEO, α-azide-ω-thiol PEO, and α-amine-ω-thiol PEO (over 98 mol%).

Original language	English
Pages (from-to)	394-401
Number of pages	8
Journal	Polymer Chemistry
Volume	7
Issue number	2
DOIs	https://doi.org/10.1039/c5py01444a
Publication status	Published - 2016 Jan 14

ASJC Scopus subject areas

Bioengineering
Biochemistry
Polymers and Plastics
Organic Chemistry

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title = "Azide-based heterobifunctional poly(ethylene oxide)s: NaN3-initiated {"}living{"} polymerization of ethylene oxide and chain end functionalizations",

abstract = "In this study, sodium azide (NaN3) was employed as a functional anionic initiator to polymerize ethylene oxide in N,N-dimethylformamide (DMF) leading to the production of the reactive polymeric alkoxide. The molecular weights of all products were controlled within the 2800-10-000 g mol-1 range on the basis of the stoichiometric balance. NaN3-initiated polymerization of ethylene oxide (EO) and chain end functionalization of the resulting alkoxide were found to be a simple and efficient method for synthesizing heterobifunctional PEOs. The reaction route via chain end tosylation of α-azide PEOs was found to yield almost quantitative functionalizations for the synthesis of α-azide-ω-tosyl PEO, α-azide-ω-thiol PEO, and α-amine-ω-thiol PEO (over 98 mol%).",

author = "Sera Yang and Youn Kim and Kim, {Hyeong Cheol} and Siddique, {Abu B.} and Gyusaang Youn and Kim, {Hyun Jun} and Park, {Hyeon Jong} and Lee, {Jae Yeol} and Sehoon Kim and Jungahn Kim",

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T2 - NaN3-initiated "living" polymerization of ethylene oxide and chain end functionalizations

AU - Yang, Sera

AU - Kim, Youn

AU - Kim, Hyeong Cheol

AU - Siddique, Abu B.

AU - Youn, Gyusaang

AU - Kim, Hyun Jun

AU - Park, Hyeon Jong

AU - Lee, Jae Yeol

AU - Kim, Sehoon

AU - Kim, Jungahn

PY - 2016/1/14

Y1 - 2016/1/14

N2 - In this study, sodium azide (NaN3) was employed as a functional anionic initiator to polymerize ethylene oxide in N,N-dimethylformamide (DMF) leading to the production of the reactive polymeric alkoxide. The molecular weights of all products were controlled within the 2800-10-000 g mol-1 range on the basis of the stoichiometric balance. NaN3-initiated polymerization of ethylene oxide (EO) and chain end functionalization of the resulting alkoxide were found to be a simple and efficient method for synthesizing heterobifunctional PEOs. The reaction route via chain end tosylation of α-azide PEOs was found to yield almost quantitative functionalizations for the synthesis of α-azide-ω-tosyl PEO, α-azide-ω-thiol PEO, and α-amine-ω-thiol PEO (over 98 mol%).

AB - In this study, sodium azide (NaN3) was employed as a functional anionic initiator to polymerize ethylene oxide in N,N-dimethylformamide (DMF) leading to the production of the reactive polymeric alkoxide. The molecular weights of all products were controlled within the 2800-10-000 g mol-1 range on the basis of the stoichiometric balance. NaN3-initiated polymerization of ethylene oxide (EO) and chain end functionalization of the resulting alkoxide were found to be a simple and efficient method for synthesizing heterobifunctional PEOs. The reaction route via chain end tosylation of α-azide PEOs was found to yield almost quantitative functionalizations for the synthesis of α-azide-ω-tosyl PEO, α-azide-ω-thiol PEO, and α-amine-ω-thiol PEO (over 98 mol%).

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JF - Polymer Chemistry

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Azide-based heterobifunctional poly(ethylene oxide)s: NaN₃-initiated "living" polymerization of ethylene oxide and chain end functionalizations

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