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

[Display omitted] •A β-cyclodextrin monomer is synthesized with excellent yield using “click” chemistry.•An ATRP protocol for the direct synthesis of sulfobetaine and β-cyclodextrin (co)polymers is presented.•Low size distributions (ĐM) and high initiator efficiencies are obtained.•Excellent host-gu...

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Bibliographic Details
Published inEuropean polymer journal Vol. 116; pp. 84 - 90
Main Authors Diget, Jakob Stensgaard, Städe, Lars Wagner, Nielsen, Thorbjørn Terndrup
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 01.07.2019
Elsevier BV
Subjects
ATRP
Chemical synthesis
Click chemistry
Copolymerization
Copolymers
Cyclodextrin
Cyclodextrins
Fractionation
Functional polymers
Monomers
NMR spectroscopy
Polymerization
Polymers
Spectrum analysis
Sulfobetaine
Temperature dependence
Titration calorimetry
UCST
Zwitterions
Sulfobetaine
Functional polymers
UCST
Cyclodextrin
Click chemistry
ATRP
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Summary:[Display omitted] •A β-cyclodextrin monomer is synthesized with excellent yield using “click” chemistry.•An ATRP protocol for the direct synthesis of sulfobetaine and β-cyclodextrin (co)polymers is presented.•Low size distributions (ĐM) and high initiator efficiencies are obtained.•Excellent host-guest binding properties of the copolymers is revealed.•The copolymer shows salt-dependent UCST behavior. 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 (ĐM = Mw/Mn) 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 ĐM 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.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2019.03.020