Abstract
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 [2]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 [2]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 [2]rotaxanes incorporating donor/acceptor Interactions.
Original language | English (US) |
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Pages (from-to) | 2565-2571 |
Number of pages | 7 |
Journal | European Journal of Organic Chemistry |
Issue number | 11 |
DOIs | |
State | Published - Nov 1998 |
Externally published | Yes |
Keywords
- Molecular recognition
- Rotaxanes
- Self-assembly
- Template-directed synthesis
ASJC Scopus subject areas
- Organic Chemistry