Dendritic pseudorotaxanes

Angewandte Chemie - International Edition

Volumn 37, Issue 23, 1998, Pages 3275-3279

  Yamaguchi, Nori ^a   Hamilton, Lesley M ^a   Gibson, Harry W ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Dendrimers; Noncovalent bonding; Pseudorotaxanes; Supramolecular chemistry

Indexed keywords

AMMONIUM DERIVATIVE; TAXANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032542386     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981217)37:23<3275::AID-ANIE3275>3.0.CO;2-9     Document Type: Article

References (30)

1. a) R. Sadamoto, N. Tomioka, T. Aida, J. Am. Chem. Soc. 1996, 118, 3978-3979;
2. b) L. L. Miller, R. G. Duan, D. C. Tully, D. A. Tomalia, J. Am. Chem. Soc. 1997, 119, 1005-1010.
3. a) J. C. M. van Hest, D. A. P. Delnoye, M. W. P. L. Baars, C. Elissen-Roman, M. H. P. van Genderen, E. W. Meijer, Chem. Eur. J. 1996, 2, 1616-1626;
4. b) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules: Concepts, Synthesis, Perspectives, VCH, Weinheim, 1996;
5. c) R. Kopelman, M. Shortreed, Z. Y. Shi, W. Tan, Z. Xu, J. S. Moore, A. Bar-Haim, J. Klafter, Phys. Rev. Lett. 1997, 78, 1239-1242;
6. d) M. Kawa, J. M. J. Fréchet, Chem. Mater. 1998, 10, 286-296.
7. a) J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, E. W. Meijer, Science 1994, 266, 1226-1229;
8. b) J. F. G. A. Jansen, E. W. Meijer, J. Am. Chem. Soc. 1995, 117, 4417-4417.
9. J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413.
10. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1991, 113, 4252-4261.
11. a) G. R. Newkome, Z. Yao, G. R. Baker, V. K. Gupta, P. S. Russo, M. J. Sanders, J. Am. Chem. Soc. 1986, 108, 849-850;
12. b) D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, P. Smith, Macromolecules 1986, 19, 2466-2468.
13. T. Kawaguchi, K. L. Walker, C. L. Wilkins, J. S. Moore, J. Am. Chem. Soc. 1995, 117, 2159-2165.
14. F. Zeng, S. C. Zimmerman, Chem. Rev. 1997, 97, 1681-1712.
15. Compound 1 has been previously reported: P. R. Ashton, A. N. Collins, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 59-62;
16. Angew. Chem. Int. Ed. Engl. 1997, 56, 59-62.
17. a) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001;
18. Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869;
19. b) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
20. a) O. Mitsunobu, Synthesis 1981, 1, 1-28;
21. b) D. L. Hughes, Org. Prep. Proced. Int. 1996, 28, 127-164.
22. [10] The lower association constant for 1:1 complex 4(5) may be attributed to the reduced accessibility and flexibility of the macrocyclic moiety of 4 due to the bulky dendritic substituent.
23. L. J. Twyman, A. E. Beezer, J. C. Mitchell, J. Chem. Soc. Perkin Trans. 1994, 4, 407-422.
24. J. C. Hummelen, J. L. J. van Dongen, E. W. Meijer, Chem. Eur. J. 1997, 5, 1489-1493.
25. a) Z. Xu, M. Kahr, K. L. Walker, C. L. Wilkins, J. S. Moore, J. Am. Chem. Soc. 1994, 116, 4537-4550;
26. b) J. W. Leon, J. M.J. Fréchet, Polym. Bull. Berlin 1995, 35, 449-455.
27. -2 M) was mixed with 1/3 mol equiv of solid 1 for 3 d. The mixture was then filtered and the filtrate was concentrated to afford a white solid, which was submitted for MALDI-MS analysis.
28. e) to minimize fragmentation. For reviews on characterization of hydrogen-bonded assemblies by ESI-MS, see: a) K. C. Russell, E. Leize, A. Van Dorsselaer, J.-M. Lehn, Angew. Chem. 1995, 107, 244-248;
29. Angew. Chem. Int. Ed. Engl. 1995, 34, 209-213;
30. b) X. Cheng, Q. Gao, R. D. Smith, E. E. Simanek, M. Mammen, G. M. Whitesides, J. Org. Chem. 1996, 61, 2204-2206.