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^*

^*Corresponding author for this work

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
Externally published	Yes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2016.

ASJC Scopus subject areas

Bioengineering
Polymers and Plastics
Biochemistry
Organic Chemistry

Access to Document

10.1039/c5py01444a

Cite this

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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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doi = "10.1039/c5py01444a",

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T1 - Azide-based heterobifunctional poly(ethylene oxide)s

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%).

UR - https://www.scopus.com/pages/publications/84952801774

U2 - 10.1039/c5py01444a

DO - 10.1039/c5py01444a

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JO - Polymer Chemistry

JF - Polymer Chemistry

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