Polyrotaxanes and Polycatenanes: Recent Advances in Syntheses and Applications of Polymers Comprising of Interlocked Structures

Takata, Toshikazu; Kihara, Nobuhiro; Furusho, Yoshio

doi:10.1007/b95529

Cited by 156 publications

(43 citation statements)

References 243 publications

(253 reference statements)

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“…It has to be admitted that mechanically bonded macromolecules with precisely controlled structures are not yet producible on a gram scale, using routine synthetic procedures. Several comprehensive review articles have been published [15][16][17] on mechanically bonded macromolecules, in addition to the extensive review literature 11,18 now available on MIMs themselves.…”

Section: Introductionmentioning

confidence: 99%

Mechanically bonded macromolecules

et al. 2010

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Mechanically bonded macromolecules constitute a class of challenging synthetic targets in polymer science. The controllable intramolecular motions of mechanical bonds, in combination with the processability and useful physical and mechanical properties of macromolecules, ultimately ensure their potential for applications in materials science, nanotechnology and medicine. This tutorial review describes the syntheses and properties of a library of diverse mechanically bonded macromolecules, which covers (i) main-chain, side-chain, bridged, and pendant oligo/polycatenanes, (ii) main-chain oligo/polyrotaxanes, (iii) poly[c2]daisy chains, and finally (iv) mechanically interlocked dendrimers. A variety of highly efficient synthetic protocols-including template-directed assembly, step-growth polymerisation, quantitative conjugation, etc.-were employed in the construction of these mechanically interlocked architectures. Some of these structures, i.e., side-chain polycatenanes and poly[c2]daisy chains, undergo controllable molecular switching in a manner similar to their small molecular counterparts. The challenges posed by the syntheses of polycatenanes and polyrotaxanes with high molecular weights are contemplated.

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Section: Introductionmentioning

confidence: 99%

Mechanically bonded macromolecules

et al. 2010

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“…9,10 In the assembly, CD molecules formed intermolecular hydrogen bonds 2,4,6,7 with each other to stay on the chain while threading and dethreading were competing, and finally a supramolecular assembly called pseudopolyrotaxane was obtained as a kinetic product. As a matter of course, some thermodynamic advantages accompanied this process, such as enthalpic gain on forming hydrogen bonds, 6 and total entropic changes on assembly of the components, as well as desolvation.…”

Section: Introductionmentioning

confidence: 99%

Modulation of reversible self-assembling of dumbbell-shaped poly(ethylene glycol)s and β-cyclodextrins: precipitation and heat-induced supramolecular crosslinking

Kobayashi

Katoono

Yamaguchi

et al. 2011

Polym J

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A series of dumbbell-shaped poly(ethylene glycol) (PEG) chains 1 attached to bulky end groups were prepared, and some of the chains formed supramolecular assemblies with b-cyclodextrin (b-CD) and its multiple, ditopic and tetratopic, derivatives. The chains with proper end groups successfully allowed b-CD to be trapped onto PEG through formation of hydrogen bonds at room temperature and higher. Mixing of the PEG chain and the ditopic supramolecular crosslinker in water at 40 1C led to a change in solution property from viscous to elastic, accompanied by a significant increase in viscosity, whereas this change was not induced at room temperature. A supramolecular network formed only when the PEG chain was mixed with the tetratopic supramolecular crosslinker at 40 1C. Once formed, the supramolecular crosslinking was maintained even after the system cooled down. Instead, dilution and shaking at room temperature resulted in a return to a solution with low viscosity. These assemblies and dissociations were affected by the end groups of 1.

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Most polyrotaxanes contain a cyclodextrine or crown ether as the wheel components. Crownether-based polyrotaxanes are easily identifiable by nuclear magnetic resonance (NMR) measurements and have a distinctive structure that provides a simple motif for the evaluation of characteristic properties of the mechanical linkage.…”

Section: Introductionmentioning

confidence: 99%

Polymer architectures assisted by dynamic covalent bonds: synthesis and properties of boronate-functionalized polyrotaxane and graft polyrotaxane

Koyama

Suzuki

Asakawa

et al. 2011

Polym J

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Poly [2]rotaxane and graft polyrotaxane were synthesized from a mixture of poly(crown ether) (polyester-10 and polyisoxazole-13) as a trunk polymer, boronic-acid-terminated secondary ammonium salt 5 as an axle component, and diol as an end-capping group by pseudorotaxane formation and subsequent catalyst-free dehydrative bondage between the boronic acid and the diol moieties. Trunk polymers 10 and 13 were prepared by copolymerization of diol-or diyne-substituted dibenzo-24-crown-8-ether 9 or 11 and ditopic comonomers such as bifunctional acid dichloride and nitrile N-oxide. The use of the sufficiently bulky and stable homoditopic nitrile N-oxide 12 gave the high-molecular-weight isoxazole-containing poly(crown ether) 13 efficiently and without accidental penetration of the propagation end into the crown cavity, which would have caused gelation. The treatment of these poly(crown ether)s with boronic acid 5 in CH 2 Cl 2 gave the corresponding polypseudorotaxanes, and subsequent graftonto reaction with pinacol and a polymeric terminal diol gave poly[2]rotaxane and graft polyrotaxane. The chemical stability of these supramolecular architectures primarily depends on the bulkiness of the diol group as the end-capping moiety and the inherence originating from the dynamic covalent bond of boronate, as determined by detailed 1 H nuclear magnetic resonance study of model [2]rotaxanes 6-8 and the dissociation behavior of the polymers.

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Polyrotaxanes and Polycatenanes: Recent Advances in Syntheses and Applications of Polymers Comprising of Interlocked Structures

Cited by 156 publications

References 243 publications

Mechanically bonded macromolecules

Mechanically bonded macromolecules

Modulation of reversible self-assembling of dumbbell-shaped poly(ethylene glycol)s and β-cyclodextrins: precipitation and heat-induced supramolecular crosslinking

Polymer architectures assisted by dynamic covalent bonds: synthesis and properties of boronate-functionalized polyrotaxane and graft polyrotaxane

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