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High Yielding Template‐Directed Syntheses of [2]Rotaxanes
Author(s) -
Bravo José A.,
Raymo Françisco M.,
Stoddart J. Fraser,
White Andrew J. P.,
Williams David J.
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2565::aid-ejoc2565>3.0.co;2-8
Subject(s) - rotaxane , chemistry , template , yield (engineering) , ring (chemistry) , catenane , acceptor , stereochemistry , cyclophane , dumbbell , crystallography , combinatorial chemistry , nanotechnology , supramolecular chemistry , molecule , organic chemistry , materials science , physics , condensed matter physics , metallurgy , medicine , physical therapy
Three dumbbell‐shaped compounds incorporating terminal triisopropylsilyl stoppers, connected to a central 1,5‐dioxynaphthalene recognition site by [–CH 2 CH 2 O–] 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.