Synthesis and characterization of a persistent paramagnetic rotaxane based on α-cyclodextrin and α,ω-alkyl disulfides |
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Authors: | Elisabetta Mezzina Paola Franchi Marco Lucarini |
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Institution: | (1) Department of Organic Chemistry “A. Mangini”, University of Bologna, Via San Giacomo 11, 40126 Bologna, Italy |
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Abstract: | A new synthetic strategy for the preparation of persistent paramagnetic cyclodextrin-based rotaxanes is described. The method
consists in the formation of inclusion complexes between α-cyclodextrin (α-CD) and α,ω-dithiols containing an octamethylene
chain covalently trapped by bulky stoppers composed of 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) radical fragments. Interaction
of α-CD (the bead) and 1,8-octanedithiol (the thread) occurs in aqueous alkaline media and encapsulation is obtained by nucleophilic
substitution at both termini of the linear component with a bulky paramagnetic iodide 2,2,6,6-tetramethyl-4-(2-iodoacetamide)piperidine-N-oxyl].
Structure determination of the new 2]rotaxane by 1H NMR is reported and the spectroscopic data are discussed. |
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Keywords: | α -Cyclodextrin Inclusion complexes Rotaxanes Nitroxides Free radicals |
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