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Cyclodextrin-Based [3]Rotaxane-Crosslinked Fluorescent Polymer: Synthesis and De-Crosslinking Using Size Complementarity.
Angew Chem Int Ed Engl
November 2018
Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan.
Vinyl-group-substituted, α-cyclodextrin-based, size-complementary [3]rotaxanes were synthesized as crosslinkers for rotaxane-crosslinked poly(methyl methacrylate) (RCP) by radical polymerization. The size complementarity of the crosslinkers made it possible to de-crosslink the RCP by heating, and the degree of decoupling was monitored by fluorescence intensity, depending on the state of the axle component of the rotaxane crosslink moiety.
View Article and Find Full Text PDFSynthesis of a Structure-Definite α-Cyclodextrin-Based Macromolecular [3]Rotaxane Using a Size-Complementary Method.
Angew Chem Int Ed Engl
September 2018
Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan.
The challenging synthesis of an α-cyclodextrin (CD)-based macromolecular rotaxane with definite structure was fulfilled using a size-complementary method. A new peracetylated (PAc) α-CD-based size-complementary [3]rotaxane was prepared and its thermal dissociation kinetics studied. The de-slippage mechanism was found to be different from that of the native α-CD-based system.
View Article and Find Full Text PDFWhich One is Bulkier: The 3,5-Dimethylphenyl or the 2,6-Dimethylphenyl Group? Development of Size-Complementary Molecular and Macromolecular [2]Rotaxanes.
Chem Asian J
April 2018
Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8552, Japan.
We developed novel size-complementary molecular and macromolecular rotaxanes using a 2,6-dimethylphenyl terminal group as the axle-end-cap group in dibenzo-24-crown-8-ether (DB24C8)-based rotaxanes, where the 2,6-dimethylphenyl group was found to be less bulky than the 3,5-dimethylphenyl group. A series of molecular and macromolecular [2]rotaxanes that bear a 2,6-dimethylphenyl group as the axle-end-cap were synthesized using unsubstituted and fluorine-substituted DB24C8. Base-induced decomposition into their constituent components confirmed the occurrence of deslipping, which supports the size-complementarity of these rotaxanes.
View Article and Find Full Text PDFCyclodextrin-based size-complementary [3]rotaxanes: selective synthesis and specific dissociation.
Chemistry
December 2014
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2888.
α-Cyclodextrin (CD)-based size-complementary [3]rotaxanes with alkylene axles were prepared in one-pot by end-capping reactions with aryl isocyanates in water. The selective formation of [3]rotaxane with a head-to-head regularity was indicated by the X-ray structural analyses. Thermal degradation of the [3]rotaxanes bearing appropriate end groups proceeded by stepwise dissociation to yield not only the original components but also [2]rotaxanes.
View Article and Find Full Text PDFSelective synthesis of a [3]rotaxane consisting of size-complementary components and its stepwise deslippage.
Org Lett
May 2012
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 (H-126), Ookayama, Meguro, Tokyo 152-8552, Japan.
An α-cyclodextrin-based size-complementary [3]rotaxane with an alkylene axle was selectively synthesized in one pot via an end-capping reaction with 2-bromophenyl isocyanate in water. Thermal degradation of the [3]rotaxane product yielded not only the original components but also the [2]rotaxane. Thermodynamic studies suggested a stepwise deslippage process.
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