Toward daisy chain polymers: "Wittig exchange" of stoppers in [2]rotaxane monomers

Organic Letters

Volumn 2, Issue 6, 2000, Pages 759-762

  Rowan, Stuart J ^a,c   Cantrill, Stuart J ^a   Stoddart, J Fraser ^a   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000555094     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9913587     Document Type: Article

References (40)

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16. Cyclic daisy chains are formed whenever chain termination of a propagating acyclic species occurs via intramolecular "backbiting".
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27. Although in not all of these reports do the authors refer to their systems as "daisy chains" or "pseudopolyrotaxanes", they all describe the noncovalent polymerization of self-complementary monomers.
28. The term pseudopolyrotaxane was introduced by us in 1994 (see ref 7) to describe polyrotaxanes that lack stoppers. Essentially, pseudopolyrotaxanes are to polyrotaxanes what pseudorotaxanes are to rotaxanes. See: Ashton, P. R.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1991, 1677-1679.
29. Alternatively, rather than employing an exchangeable stopper, a stopper bearing a reactive functional group may be used. For an example, see: Werts, M. P. L.; van den Boogaard, M.; Hadziioannou, G.; Tsivgoulis, G. M. Chem. Commun. 1999, 623-624.
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32. Rowan, S. J.; Stoddart, J. F. Unpublished results.
33. Previous results have shown that substitution of the dibenzylammonium ion component with electron-withdrawing groups increases its affinity for DB24C8. Conversely, substitution with electron-donating groups causes a corresponding decrease in the association constants. See: Ashton, P. R.; Fyfe, M. C. T.; Hickingbottom, S. K.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Perkin Trans. 2 1998, 2117-2128.
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35. -1, F(000) = 1357, T = 293 K; clear blocky prisms, 0.50 × 0.40 × 0.40 mm, Siemens P4/RA diffractometer, graphite-monochromated Cu Kα radiation, ω-scans, 9529 independent reflections.
36. Rowan, S. J.; Stoddart, J. F.; Williams, D. J. Unpublished results.
37. 6 exists in two cycloenantiomeric forms. For the first example of a cycloenantiomeric rotaxane, see: Yamamoto, C.; Okamoto, Y.; Schmidt, T.; Jäger, R.; Vögtle, F. J. Am. Chem. Soc. 1997, 119, 10547-10548. For a cyclodiastereoisomeric [3]rotaxane, see: Schmeider, R.; Hübner, G.; Seel, C.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 3528-3530.
38. 6 exists in two cycloenantiomeric forms. For the first example of a cycloenantiomeric rotaxane, see: Yamamoto, C.; Okamoto, Y.; Schmidt, T.; Jäger, R.; Vögtle, F. J. Am. Chem. Soc. 1997, 119, 10547-10548. For a cyclodiastereoisomeric [3]rotaxane, see: Schmeider, R.; Hübner, G.; Seel, C.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 3528-3530.
39. 6 highlights the potential for formation of diastereoisomeric cyclic dimers, i.e., it is not only possible to generate the RR and SS dimers (an enantiomeric pair) but also the "meso" achiral RS dimer.
40. 2 signal is shifted upfield to a δ value of ∼3.7 ppm.