Direct synthesis of well-defined zwitterionic cyclodextrin polymers via atom transfer radical polymerization

Jakob Stensgaard Diget; Lars Wagner Städe; Thorbjørn Terndrup Nielsen

doi:10.1016/j.eurpolymj.2019.03.020

Direct synthesis of well-defined zwitterionic cyclodextrin polymers via atom transfer radical polymerization

Jakob Stensgaard Diget^*, Lars Wagner Städe, Thorbjørn Terndrup Nielsen

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

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Abstract

A versatile atom transfer radical polymerization (ATRP) protocol was developed for the direct homo- and copolymerization of a sulfobetaine monomer, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium (SBMA), and a mono-functionalized β-cyclodextrin (βCD) methacrylate monomer. The polymers were characterized using 1- and 2D NMR spectroscopy and asymmetrical flow field-flow fractionation (AF4). Low dispersities (Đ _M = M _w /M _n ) and high initiator efficiencies, of both the homo- and copolymers, indicated good control of the polymerization. The work thus represents one of the few reports where low Đ _M values are obtained for direct ATRP of SBMA and βCD monomers. The novel βCD copolymer showed salt-dependent upper critical solution temperature (UCST) behavior, while isothermal titration calorimetry revealed excellent binding properties.

Original language	English
Journal	European Polymer Journal
Volume	116
Pages (from-to)	84-90
Number of pages	7
ISSN	0014-3057
DOIs	https://doi.org/10.1016/j.eurpolymj.2019.03.020
Publication status	Published - 1 Jul 2019

Keywords

ATRP
Click chemistry
Cyclodextrin
Functional polymers
Sulfobetaine
UCST

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10.1016/j.eurpolymj.2019.03.020

Direct-synthesis-of-well-defined-zwitterionic-cyclodextrin_2019_European-PolAccepted author manuscript, 1.07 MBLicence: CC BY-NC-ND 4.0

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@article{2058a580d75d42a78f325754bdba2b71,

title = "Direct synthesis of well-defined zwitterionic cyclodextrin polymers via atom transfer radical polymerization",

abstract = " A versatile atom transfer radical polymerization (ATRP) protocol was developed for the direct homo- and copolymerization of a sulfobetaine monomer, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium (SBMA), and a mono-functionalized β-cyclodextrin (βCD) methacrylate monomer. The polymers were characterized using 1- and 2D NMR spectroscopy and asymmetrical flow field-flow fractionation (AF4). Low dispersities ({\D} M = M w /M n ) and high initiator efficiencies, of both the homo- and copolymers, indicated good control of the polymerization. The work thus represents one of the few reports where low {\D} M values are obtained for direct ATRP of SBMA and βCD monomers. The novel βCD copolymer showed salt-dependent upper critical solution temperature (UCST) behavior, while isothermal titration calorimetry revealed excellent binding properties. ",

keywords = "ATRP, Click chemistry, Cyclodextrin, Functional polymers, Sulfobetaine, UCST",

author = "Diget, {Jakob Stensgaard} and St{\"a}de, {Lars Wagner} and Nielsen, {Thorbj{\o}rn Terndrup}",

year = "2019",

month = jul,

day = "1",

doi = "10.1016/j.eurpolymj.2019.03.020",

language = "English",

volume = "116",

pages = "84--90",

journal = "European Polymer Journal",

issn = "0014-3057",

publisher = "Pergamon Press",

}

TY - JOUR

T1 - Direct synthesis of well-defined zwitterionic cyclodextrin polymers via atom transfer radical polymerization

AU - Diget, Jakob Stensgaard

AU - Städe, Lars Wagner

AU - Nielsen, Thorbjørn Terndrup

PY - 2019/7/1

Y1 - 2019/7/1

N2 - A versatile atom transfer radical polymerization (ATRP) protocol was developed for the direct homo- and copolymerization of a sulfobetaine monomer, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium (SBMA), and a mono-functionalized β-cyclodextrin (βCD) methacrylate monomer. The polymers were characterized using 1- and 2D NMR spectroscopy and asymmetrical flow field-flow fractionation (AF4). Low dispersities (Đ M = M w /M n ) and high initiator efficiencies, of both the homo- and copolymers, indicated good control of the polymerization. The work thus represents one of the few reports where low Đ M values are obtained for direct ATRP of SBMA and βCD monomers. The novel βCD copolymer showed salt-dependent upper critical solution temperature (UCST) behavior, while isothermal titration calorimetry revealed excellent binding properties.

AB - A versatile atom transfer radical polymerization (ATRP) protocol was developed for the direct homo- and copolymerization of a sulfobetaine monomer, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium (SBMA), and a mono-functionalized β-cyclodextrin (βCD) methacrylate monomer. The polymers were characterized using 1- and 2D NMR spectroscopy and asymmetrical flow field-flow fractionation (AF4). Low dispersities (Đ M = M w /M n ) and high initiator efficiencies, of both the homo- and copolymers, indicated good control of the polymerization. The work thus represents one of the few reports where low Đ M values are obtained for direct ATRP of SBMA and βCD monomers. The novel βCD copolymer showed salt-dependent upper critical solution temperature (UCST) behavior, while isothermal titration calorimetry revealed excellent binding properties.

KW - ATRP

KW - Click chemistry

KW - Cyclodextrin

KW - Functional polymers

KW - Sulfobetaine

KW - UCST

UR - http://www.scopus.com/inward/record.url?scp=85063966250&partnerID=8YFLogxK

U2 - 10.1016/j.eurpolymj.2019.03.020

DO - 10.1016/j.eurpolymj.2019.03.020

M3 - Journal article

AN - SCOPUS:85063966250

SN - 0014-3057

VL - 116

SP - 84

EP - 90

JO - European Polymer Journal

JF - European Polymer Journal

ER -

Direct synthesis of well-defined zwitterionic cyclodextrin polymers via atom transfer radical polymerization

Abstract

Keywords

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