Cyclodextrin-Containing Polymers. 1. Preparation of Polymers

Harada, Akira; Furue, Masaoki; Nozakura, Shun‐ichi

doi:10.1021/ma60053a003

Cited by 129 publications

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“…1 • 2 In the preceding· papers the authors reported the preparation of certain vinyl polymers containing cyclodextrins 3 and their catalytic and inclusion behavior. 4 The polymers containing {3-CD were found to bind to large substrates having two guest parts more efficiently than {3-CD but to bind to small substrates having one guest part less efficiently than {3-CD.…”

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Inclusion of Aromatic Compounds by a β-Cyclodextrin–Epichlorohydrin Polymer

Harada

Furue

Nozakura

1981

Polym J

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ABSTRACT:A condensation polymer (/3-CD-E) of {3-CD with epichlorohydrin was compared with P-CD and poly(/3-CD acrylate) in regard to inclusion behavior in an aqueous solution. The stability of the inclusion complexes of P-CD-E with substrates of a single guest part is smaller than that of P-CD because of steric hindrance by substituents on {3-CD. On the other hand, the stability of P-CD-E complexes for substrates with two guest parts is much larger than that of {3-CD and is somewhat smaller than that of poly(/3-CD acrylate). This is due to the cooperation in binding of the adjacent two CD units on a polymer chain.KEY WORDS P-Cyclodextrin I Epichlorohydrin I P-Cyclodextrin Polymer I Inclusion I Fluorescence I Sodium 2-p-Toluidinylnaphthalene-6-sulfonate I Binding I Dansylamino Acid I Cyclodextrins (CD) are known to form noncovalent inclusion complexes with various organic molecules in aqueous solution. 1 • 2 In the preceding· papers the authors reported the preparation of certain vinyl polymers containing cyclodextrins 3 and their catalytic and inclusion behavior. 4 The polymers containing {3-CD were found to bind to large substrates having two guest parts more efficiently than {3-CD but to bind to small substrates having one guest part less efficiently than {3-CD. It was concluded that this polymer effect on the formation of complexes with large substrates was caused by the cooperation of two adjacent {3-CD moieties on a polymer chain. 5 This conclusion is supported by an inclusion study using the model dimers of In this paper, the study of the polymer effect on the inclusion by {3-CD was extended to a condensation polymer of {3-CD, the preparation of which is already known 7 and is much easier than that of vinyl polymers. 3 RESULTS AND DISCUSSION Characterization of {3-CD-E

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“…6 In this paper, the study of the polymer effect on the inclusion by {3-CD was extended to a condensation polymer of {3-CD, the preparation of which is already known 7 and is much easier than that of vinyl polymers. 3 …”

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Inclusion of Aromatic Compounds by a β-Cyclodextrin–Epichlorohydrin Polymer

Harada

Furue

Nozakura

1981

Polym J

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“…[1] Wir beschreiben hier die Synthese eines CD-haltigen Polymers unter Beteiligung einer 1,3-dipolaren Cycloaddition, die auch als Klick-Reaktion bezeichnet wird. Diese verläuft ohne Nebenreaktionen und ermög-licht den Zugang zu komplexen Strukturen in hohen Ausbeuten.…”

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Pseudopolyanionen aus Poly(NIPAAM‐co‐β‐Cyclodextrinmethacrylat) und ionischen Flüssigkeiten

et al. 2008

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Flexible Gastgeber: Copolymere aus methacryliertem β‐Cyclodextrin und N‐Isopropylacrylamid bilden Einschlusskomplexe mit Anionen ionischer Flüssigkeiten (siehe Bild). Die Komplexbildung verändert die Löslichkeitseigenschaften des Copolymers und führt zu „Pseudopolyelektrolyten“. Trübungs‐ und dynamische Lichtstreumessungen ergeben, dass es je nach Anion zu einer Schrumpfung oder Ausdehnung der Polymerkette aufgrund elektrostatischer Effekte kommt.

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“…1 • 2 Previously, we prepared polymers containing cyclodextrins in order to enhance the stability of complexes and to achieve better selectivity. 3 Polymers containing /3-CD were found to bind with large substrates which were too large to be accomodated in a single cavity more efficiently than /3-CD. 4 The polymer complexes showed exclusively 2 : 1 stoichiometry even in the concentration range where the complex of /3-CD showed 1: 1 stoichiometry.…”

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Cooperative Binding by Cyclodextrin Dimers

Harada

Furue

Nozakura

1980

Polym J

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ABSTRACT:Dimers containing P-cyclodextrin (P-CD) moieties at both ends of dicarboxylic acids were prepared by the reaction ofbis(m-nitrophenyl) dicarboxylate with a large excess of P-CD, and were purified by dialysis and gel chromatography. The interaction of the dimers with potassium 2-p-toluidinylnaphthalene-6-sulfonate (TNS) was studied by the fluorescence technique and compared with that of P-CD and poly(acryloyl-P-CD). The dimers were found to bring about a much greater enhancement and blue shift of the TNS fluorescence than P-CD but less than the polymer. The succinate dimer enhanced the TNS fluorescence twofold more than the glutarate dimer. Dissociation constants and stoichiometries were determined by fluorometric titration and continuous variation methods. The dimer complexes showed exclusively 2: I stoichiometry (CD: TNS), even in the concentration range in which P-CD showed I : I stoichiometry. The 2: I complexes of the dimers were much more stable than the 2: I complex of P-CD and were comparable to that of the polymer. Thus, two CD units linked by the chain were found to cooperate in binding one TNS molecule.KEY WORDS Cyclodextrin / Cyclodextrin Dimer / Bis(cyclodextrin) Succinate / Bis(cyclodextrin) Glutarate / 2-p-Toluidinylnaphthalene-6-sulfonate / Fluorescence / Binding / Inclusion / Cyclodextrins (CD) are well known to form inclusion complexes with various molecules in aqueous solutions. The inclusion properties of CDs have been well investigated by a variety of physicochemical techniques and the results have been reviewed. 1 • 2 Previously, we prepared polymers containing cyclodextrins in order to enhance the stability of complexes and to achieve better selectivity. 3

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Cyclodextrin-Containing Polymers. 1. Preparation of Polymers

Cited by 129 publications

References 1 publication

Inclusion of Aromatic Compounds by a β-Cyclodextrin–Epichlorohydrin Polymer

Inclusion of Aromatic Compounds by a β-Cyclodextrin–Epichlorohydrin Polymer

Pseudopolyanionen aus Poly(NIPAAM‐co‐β‐Cyclodextrinmethacrylat) und ionischen Flüssigkeiten

Cooperative Binding by Cyclodextrin Dimers

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