Selenonium polyelectrolyte synthesis through post-polymerization modifications of poly (Glycidyl methacrylate) scaffolds

Taejun Eom; Anzar Khan

doi:10.3390/polym12112685

Selenonium polyelectrolyte synthesis through post-polymerization modifications of poly (Glycidyl methacrylate) scaffolds

Taejun Eom, Anzar Khan

Department of Chemical and Biological Engineering

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

3 Citations (Scopus)

Abstract

Atom transfer radical polymerization of glycidyl methacrylate monomer with poly(ethylene glycol)-based macroinitiators leads to the formation of reactive block copolymers. The epoxide side-chains of these polymers can be subjected to a regiospecific base-catalyzed nucleophilic ring-opening reaction with benzeneselenol under ambient conditions. The ß-hydroxy selenide linkages thus formed can be alkylated to access polyselenonium salts.⁷⁷ Se-NMR indicates the formation of diastereomers upon alkylation. In such a manner, sequential post-polymerization modifications of poly(glycidyl methacrylate) scaffolds via selenium-epoxy and selenoether alkylation reactions furnish practical access to poly(ethylene glycol)-based cationic organoselenium copolymers.

Original language	English
Article number	2685
Pages (from-to)	1-9
Number of pages	9
Journal	Polymers
Volume	12
Issue number	11
DOIs	https://doi.org/10.3390/polym12112685
Publication status	Published - 2020 Nov 2

Keywords

Epoxide ring-opening reaction
Organoselenium polymers
Poly(glycidyl methacrylate)s
Polyselenonium salts
Selenium-epoxy reaction

ASJC Scopus subject areas

Chemistry(all)
Polymers and Plastics

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10.3390/polym12112685

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title = "Selenonium polyelectrolyte synthesis through post-polymerization modifications of poly (Glycidyl methacrylate) scaffolds",

abstract = "Atom transfer radical polymerization of glycidyl methacrylate monomer with poly(ethylene glycol)-based macroinitiators leads to the formation of reactive block copolymers. The epoxide side-chains of these polymers can be subjected to a regiospecific base-catalyzed nucleophilic ring-opening reaction with benzeneselenol under ambient conditions. The {\ss}-hydroxy selenide linkages thus formed can be alkylated to access polyselenonium salts.77 Se-NMR indicates the formation of diastereomers upon alkylation. In such a manner, sequential post-polymerization modifications of poly(glycidyl methacrylate) scaffolds via selenium-epoxy and selenoether alkylation reactions furnish practical access to poly(ethylene glycol)-based cationic organoselenium copolymers.",

keywords = "Epoxide ring-opening reaction, Organoselenium polymers, Poly(glycidyl methacrylate)s, Polyselenonium salts, Selenium-epoxy reaction",

author = "Taejun Eom and Anzar Khan",

note = "Funding Information: Funding: This research was funded by National Research Foundation of Korea grant funded by the Korean government (MSIP) (NRF-18R1D1A1B07048527). Publisher Copyright: {\textcopyright} MDPI AG. All rights reserved.",

year = "2020",

month = nov,

day = "2",

doi = "10.3390/polym12112685",

language = "English",

volume = "12",

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journal = "Polymers",

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T1 - Selenonium polyelectrolyte synthesis through post-polymerization modifications of poly (Glycidyl methacrylate) scaffolds

AU - Eom, Taejun

AU - Khan, Anzar

N1 - Funding Information: Funding: This research was funded by National Research Foundation of Korea grant funded by the Korean government (MSIP) (NRF-18R1D1A1B07048527). Publisher Copyright: © MDPI AG. All rights reserved.

PY - 2020/11/2

Y1 - 2020/11/2

N2 - Atom transfer radical polymerization of glycidyl methacrylate monomer with poly(ethylene glycol)-based macroinitiators leads to the formation of reactive block copolymers. The epoxide side-chains of these polymers can be subjected to a regiospecific base-catalyzed nucleophilic ring-opening reaction with benzeneselenol under ambient conditions. The ß-hydroxy selenide linkages thus formed can be alkylated to access polyselenonium salts.77 Se-NMR indicates the formation of diastereomers upon alkylation. In such a manner, sequential post-polymerization modifications of poly(glycidyl methacrylate) scaffolds via selenium-epoxy and selenoether alkylation reactions furnish practical access to poly(ethylene glycol)-based cationic organoselenium copolymers.

AB - Atom transfer radical polymerization of glycidyl methacrylate monomer with poly(ethylene glycol)-based macroinitiators leads to the formation of reactive block copolymers. The epoxide side-chains of these polymers can be subjected to a regiospecific base-catalyzed nucleophilic ring-opening reaction with benzeneselenol under ambient conditions. The ß-hydroxy selenide linkages thus formed can be alkylated to access polyselenonium salts.77 Se-NMR indicates the formation of diastereomers upon alkylation. In such a manner, sequential post-polymerization modifications of poly(glycidyl methacrylate) scaffolds via selenium-epoxy and selenoether alkylation reactions furnish practical access to poly(ethylene glycol)-based cationic organoselenium copolymers.

KW - Epoxide ring-opening reaction

KW - Organoselenium polymers

KW - Poly(glycidyl methacrylate)s

KW - Polyselenonium salts

KW - Selenium-epoxy reaction

UR - http://www.scopus.com/inward/record.url?scp=85096208781&partnerID=8YFLogxK

U2 - 10.3390/polym12112685

DO - 10.3390/polym12112685

M3 - Article

AN - SCOPUS:85096208781

SN - 2073-4360

VL - 12

SP - 1

EP - 9

JO - Polymers

JF - Polymers

IS - 11

M1 - 2685

ER -

Selenonium polyelectrolyte synthesis through post-polymerization modifications of poly (Glycidyl methacrylate) scaffolds

Abstract

Keywords

ASJC Scopus subject areas

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