Self-assembly of dendrimers by slippage

Organic Letters

Volumn 4, Issue 21, 2002, Pages 3565-3568

  Elizarov, Arkadij M ^a   Chang, Theresa ^a   Chiu, Sheng Hsien ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

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ARTICLE;

EID: 0038447296     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026479c     Document Type: Article

References (36)

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11. Supramolecular dendrimers are comprised of noncovalently bonded subunits: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098.
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16. Noncovalently bonded aggregates wherein each component is considered to be a dendrimer: (a) Percec, V.; Cho, W.-D.; Mosier, P. E.; Ungar, G.; Yeardley, J. P. J. Am. Chem. Soc. 1998, 120, 11061-11070.
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21. The slippage methodology was exploited early on when rotaxanes were prepared in a statistical manner. For examples see: (a) Harrison, I. T. J Chem. Soc., Chem. Commun. 1972, 231-232.
22. (b) Schill, G.; Beckmann, W.; Schweikert, N.; Fritz, H. Chem. Ber. 1986, 119, 2647-2655. The first successful template-directed synthesis of rotaxanes by slippage was reported in 1993.
23. See: (c) Ashton, P. R.; Belohradsky, M.; Philp, D.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1993, 1269-1274.
24. For a discussion of the phenomenon see: (d) Fyfe, M. C. T.; Raymo, F. M.; Stoddart, J. F. In Stimulating Concepts in Chemistry; Shibasaki, M., Stoddart, J. F., Vögtle, F., Eds.; VCH-Wiley: Weinheim, Germany, 2000; pp 211-220.
25. For recent examples see: (e) Sohgawa, Y. H.; Fujimori, H.; Shoji, J.; Furusho, Y.; Kihara, N.;: Takata, T. Chem. Lett. 2001, 8, 774-775.
26. (f) Jeppesen, J. O.; Becher, J.; Stoddart, J. F. Org. Lett. 2002, 4, 557-560.
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28. An initial slippage experiment, which was performed (ref 10) with the concentrations of both components at 10 mM, afforded the [2]rotaxane in appreciable quantities after 16 weeks! As expected, increasing the concentrations and using an excess of DB24C8 resulted in a higher yield of the [2]rotaxane in a shorter time.
29. Pollak, K. W.; Sanford, E. M.; Fréchet, J. M. J. J. Mater. Chem. 1998, 8, 519-527.
30. The synthesis of 4 is also outlined in Scheme 1. In the reaction of triethyleneglycol bistosylate (6) with 3,4-dihydroxybenzaldehyde in the presence of a base, only one pure isomer, namely 7, is isolated. The regioselectivity, expressed doubly in this nucleophilic substitution, is believed to be dictated by the stabilization of the phenoxide ion in the position para to the formyl group. See: (a) Reitz, A.; Avery, M. A.; Verlander, M. S.; Goodman, M. J. Org. Chem. 1981, 46, 4889-4863.
31. (b) Allwood, B.; Kohnke, F. H.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1985, 311-314.
32. 3 (see Supporting Information) is consistent with the presence of only one isomer, i.e., compound 7, as already reported in the literature.
33. The ability to assemble and disassemble dendrimers where hydrogen bonding between the components is complemented by a mechanical bond renders the rotaxane-like dendrimer much more stable than a conventional supramolecular dendrimer where multiple hydrogen bonds, even when they act cooperatively, lead to dynamic superstructures for the most part, i.e., the mechanical bond can be employed to bring added stability to supramolecular dendrimers based on hydrogen-bonding interactions.
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