Synthesis of a polypseudorotaxane, polyrotaxane, and polycatenane using 'click' chemistry

Bria, M., Bigot, J., Cooke, G. , Lyskawa, J., Rabani, G., Rotello, V. M. and Woisel, P. (2009) Synthesis of a polypseudorotaxane, polyrotaxane, and polycatenane using 'click' chemistry. Tetrahedron, 65(1), pp. 400-407. (doi:10.1016/j.tet.2008.10.005)

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Abstract

The synthesis of a polypseudorotaxane, polyrotaxane, and polycatenane containing the electron-deficient cyclophane cyclobis(paraquat-p-phenylene) (CBPQT(4+)) subunit in the side chain is described. These interlocked supramolecular polymers have been prepared from an azide-functionalized polystyrene derivative and an acetylene-functionalized [2]rotaxane, [2]catenane and their parent tetracationic cyclophane via Cu(I)-catalyzed 1,3 dipolar cycloadditions ('click chemistry'). The synthesis and characterization of the polymers and intermediates has been described using IR, H-1 NMR, UV spectroscopies, and voltammetry. We have shown that the CBPQT(4+) unit of the side chain polystyrene derivative has the ability to reversibly undergo complexation with a complementary dialkoxynaphthatene derivative. .

Item Type:Articles
Keywords:1,3-DIPOLAR CYCLOADDITIONS <2>CATENANE ARCHITECTURES CATALYZED AZIDE-ALKYNE CHAIN CHEMISTRY Click chemistry CYCLOBIS(PARAQUAT-P-PHENYLENE) Interlocked molecules INTERLOCKED STRUCTURES IR MOLECULAR MECCANO NMR POLYMERS rotaxanes SOLID-PHASE SPECTROSCOPY SUPRAMOLECULAR POLYMERS TERMINAL ALKYNES UNIT
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Cooke, Professor Graeme and Rabani, Dr Gouher
Authors: Bria, M., Bigot, J., Cooke, G., Lyskawa, J., Rabani, G., Rotello, V. M., and Woisel, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
ISSN:0040-4020

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