Toward globular macromolecules with functionalized interiors: Design and synthesis of dendrons with an interesting twist

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1961-1964

  Bharathi, Pandi ^a   Zhao, Hongda ^a   Thayumanavan, S ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001291527     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016064b     Document Type: Article

References (42)

1. (a) Cram, D. J. Nature 1992, 356, 29.
2. (b) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
3. (c) Breslow, R. Acc. Chem. Res. 1995, 28, 146.
4. (d) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647.
5. (e) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931.
6. (f) Rowan, A. E.; Elemans, J. A. A. W.; Nolte, R. J. M. Acc. Chem. Res. 1999, 32, 995.
7. (g) Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812.
8. (a) Fréchet, J. M. J. Science 1994, 263, 1710.
9. (b) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendritic Molecules. Concepts, Synthesis, Perspectives; VCH: Weinheim, 1996.
10. (c) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
11. (d) Tomalia. D. A. Adv. Mater. 1994, 6, 529.
12. (e) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665.
13. (f) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 884.
14. (g) Frey, H. Angew. Chem., Int. Ed. 1998, 37, 2193.
15. (h) Matthews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1.
16. (i) Moore, J. S. Acc. Chem. Res. 1997, 30, 402.
17. (j) Newkome. G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689.
18. (k) Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681.
19. Percec, V.; Cho, W. D.; Ungar, G. J. Am. Chem. Soc. 2000, 122, 10273 and references therein.
20. Smith, D. K.; Diederich, F. Chem. Eur. J. 1998, 4, 1353.
21. (a) Newkome, G. R.; Moorefield, C. N.; Baker, G. R.; Saunders, M. J.; Grossman, S. H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1178.
22. (b) Hawker, C. J., Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1993, 1287.
23. (c) Jansen, J. F. G. A.; Berg, E. M. M. d. B.-v. d.; Meijer, E. W. Science 1994, 266, 1226.
24. (d) Jansen, J. F. G. A.; Meijer, E. W.; Berg, E. M. M. d. B.-v. d. J. Am. Chem. Soc. 1995, 117, 4417.
25. (e) Baars, M. W. P. L.; Kleppinger, R.; Koch, M. H. J.; Yeu, S.-L.; Meijer, E. W. Angew. Chem., Int. Ed. 2000, 39, 1285.
26. (f) Watkins, D. M.; Sayed-Sweet, Y.; Klimash, J. W.; Turro, N. J.; Tomalia, D. A. Langmuir 1997, 13, 3130.
27. (g) Cooper, A. I.; Londono, J. D.; Wignall, G.; McClain, J. B.; Samulski, E. T.; Lin, J. S.; Dobrynin, A.; Rubinstein, M.; Burke, A. L. C.; Fréchet, J. M. J.; DeSimone, J. M. Nature 1997, 389, 368.
28. (h) Pan, Y.; Ford, W. T. Macromolecules 2000, 33, 3731.
29. (i) Chen, W.; Tomalia, D. A.; Thomas, J. L. Macromolecules 2000, 33, 9169.
30. (j) Crooks, R. M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L. K. Acc. Chem. Res. 2001, 34, 181.
31. (a) Cheng, Y.; Ho, D. M.; Gottlieb, C. R.; Kahne, D. J. Am. Chem. Soc. 1992, 114, 7319.
32. (b) Venkatesan, P.; Cheng, Y.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6955.
33. (c) McQuade, D. T.; Barrett, D. G.; Desper, J. M.; Hayashi, R. K.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 4862.
34. (d) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640.
35. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
36. We note that the biphenyl linkage in 1 does not necessarily result in a 90° twist. With a crude modeling study using Chem-3D, we noticed a twist of about 60° for the monomer 1. This twist is sufficient for our goal of placing functionality toward dendritic interiors.
37. (a) Hoye, T. R.; Chen, M. J. Org. Chem. 1996, 61, 7940.
38. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
39. Suzuki coupling was attempted with various bases and solvents to optimize the yield. For a study that shows that the nature of the base significantly affects the yields, see: Griffiths, C.; Leadbeater, N. E. Tetrahedron Lett. 2000, 41, 2487-2490.
40. Dol, G. C.; Kamer, P. G. J.; van Leeuwen, P. W. N. M. Eur. J. Org. Chem. 1998, 359-364.
41. See Supporting Information for the experimental details.
42. For an example, see: Xu, Z.; Bernlohr, D. A.; Banaszak, L. J. J. Biol. Chem. 1993, 268, 7874-7884.