Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Three dumbbell-shaped compounds incorporating terminal triisopropylsilyl stoppers, connected to a central 1,5-dioxynaphthalene recognition site by [-CH2CH2O-]n spacers (n = 1-3), have been synthesized. These compounds have been employed as templates for the synthesis of rotaxanes incorporating cyclobis(paraquat-p-phenylene) as the ring component. It was found that the length of the polyether chains of the templates influences the efficiencies of the template-directed syntheses. Rotaxane formation occurs only if n 〉 1 and, when n = 3 the corresponding rotaxane can be isolated in a yield as high as 72 %. This remarkable yield is the highest ever obtained for the template-directed syntheses of rotaxanes incorporating donor/acceptor interactions.
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