Construction of giant dendrimers using a tripodal building block

Journal of the American Chemical Society

Volumn 125, Issue 24, 2003, Pages 7250-7257

  Ruiz, Jaime ^a   Lafuente, Gustavo ^a   Marcen, Sylvia ^a   Ornelas, Catia ^a   Lazare, Sylvain ^a   Cloutet, Eric ^b   Blais, Jean Claude ^c   Astruc, Didier ^a  

^a CNRS   (France)

^b UNIVERSITÉ BORDEAUX 1   (France)

^c SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEAR MAGNETIC RESONANCE; SILICON; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ORGANO-SILICON DENDRIMERS;

DENDRIMERS;

DENDRIMER; PHENOL DERIVATIVE;

ACCURACY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROSILYLATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NUCLEOTIDE SEQUENCE; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TECHNIQUE;

EID: 0038053104     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021147o     Document Type: Article

References (50)

1. (a) Tomalia, D. A.; Taylor, A. N., Goddard, W. A., III. Angew. Chem. Int. Ed. Engl. 1990, 29, 138-175.
2. (b) Fréchet, J. M. J. Science, 1994, 263, 1710-1715.
3. (c) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875-909.
4. (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses and Applications; VCH: Weinheim, 2001.
5. (b) Advances in Dendritic Molecules; Newkome, G., Ed.; JAI: Greenwich, CT, Vols. 1-5, 1994-1998 and 2002.
6. (c) Dendrimers, Topics in Current Chemistry; Vögtle, F., Ed.; Springer-Verlag: Berlin, Vol. 1, 1997; and Vol 2, 2000.
7. (d) Dendrimers and Other Dendritic Polymers; Tomalia, D., Fréchet, J. M. J., Eds.; Wiley-VCH: New York, 2002.
8. Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
9. Matthews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1-56.
10. Venturi, M.; Serroni, S.; Juris, A.; Campagna, S.; Balzani, V. In Dendrimers, Topics in Current Chemistry; Vögtle, F., Ed.; Springer-Verlag: Berlin, 1998; Vol. 197, pp 193-228.
11. (a) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
12. (b) Sijbesma, R. P.; Meijer, E. W. Curr. Opin. Coll. Int. Sci. 1999, 4, 24-34.
13. (c) Weener, J.-W.; Baars, M. W. P. L.; Meijer, E. W. In ref 2d, pp 387-424.
14. (d) Bosman, A. W.; Bruining, M. J.; Kooijman; Spek, A. L.; Janssen, R. A. J.; Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 5547-8548.
15. (a) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74-91.
16. (b) Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819-3867.
17. (c) Aliphatic ester dendrimers up to 30 711 Da and 192 masked hydroxyl groups (in six generations) have recently been conveniently prepared in high yield and purity: Ihre, H.; Padilla De Jesús, O. L.; Fréchet, J. M. J. J. Am. Chem. Soc. 2001, 123, 5908-5917.
18. Crooks, R. M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L. K. Acc. Chem. Res. 2001, 34, 181-190.
19. Tomalia, D. A.; Baker, H.; Dewald, J. R.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466-2470.
20. van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466-468.
21. Caminade, A. M.; Majoral, J. P. In Dendrimers, Topics in Current Chemistry; Vögtle, F., Ed.; Springer: Berlin, 1998; pp 79-124.
22. Sournies, F.; Crasnier, F.; Graffeuil, M.; Faucher, J.-P.; Lahana, R.; Labarre, M. C.; Labarre, J.-F. Angew. Chem., Int. Ed. Engl. 1995, 34, 578-581.
23. De Gennes, P.-G.; Hervet, H. J. Phys. Lett. 1983, 44, 351-360.
24. Percec, V.; Johansson, G.; Ungar, G.; Zhou, J. P. J. Am. Chem. Soc. 1996, 18, 9855-9866.
25. Lescanec, R. L.; Muthukumar, M. Macromolecules 1990, 23, 2280-2288.
26. (a) Mansfield, M. L.; Klushin, L. I. Macromolecules 1993, 26, 4262-4268.
27. (b) Boris, D.; Rubinstein, M. Macromolecules 1996, 29, 7251-7260.
28. Naidoo, K. J.; Hughes, S. J.; Moss, J. R. Macromolecules 1999, 32, 331-341.
29. Mourey, T. H.; Turner, S. R.; Rubinstein, M.; Fréchet, J. M. J.; Hawker, C. J.; Wooley, K. L. Macromolecules 1992, 25, 2401-2406.
30. Wooley, K. L.; Klug, C. A.; Tasaki, K.; Schaefer, J. J. Am. Chem. Soc. 1997, 119, 53-58.
31. Meltzer, A. D.; Tirrell, D. A.; Jones, A. A.; Inglefield, P. T.; Hedstrand, D. M.; Tomalia, D. A. Macromolecules 1992, 25, 4549-4552.
32. De Backer, S.; Prinzie, Y.; Verheijen, W.; Smet, M.; Desmedt, K.; Dehaen, W.; De Schryver, F. C. J. Phys. Chem. A 1998, 102, 5451-5455.
33. Sartor, V.; Djakovitch, L.; Fillaut, J.-L.; Moulines, F.; Neveu, F.; Marvaud, V.; Guittard, J.; Blais, J.-C.; Astruc, D. J. Am. Chem. Soc. 1999, 121, 2929-2930.
34. Krsda, S. W.; Seyferth, D. J. Am. Chem. Soc. 1998, 120, 3604-3612.
35. 2OH group was recently reported: Tacke, R.; Handmann, V. I. Organometallics 2002, 21, 2619-2625.
36. Hierleman, A.; Campbell, J. K.; Crooks, A. M.; Rico, A. J. J. Am. Chem. Soc. 1998, 120, 5323-5324.
37. Li, J.; Swanson, D. R.; Qin, D.; Brothers, H. M.; Piehler, L. T.; Tomalia, D.; Meier, J. Langmuir 1999, 15, 7347-7350.
38. Tsukruk, V. V.; Rinderspacher, F.; Bliznyuk, V. N. Langmuir 1997, 13, 2171-2176.
39. Sheiko, S. S.; Gauthier, M.; Möller, M. Macromolecules 1997, 30, 2343-2349.
40. Díaz, D. J.; Storrier, G. D.; Bernhard, S.; Takada, K.; Abruña, H. D. Langmuir 1999, 15, 7351-7354.
41. Sano, M.; Okamura, J.; Ikeda, A.; Shinkai, S. A. Langmuir 2001, 17, 1807-1810.
42. Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003-2004.
43. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, 1995.
44. For improved detailed experimental procedure, see: Astruc, D. In Electron Transfer in Chemistry; Balzani, V., Ed.; VCH-Wiley: New York, Vol. 2, 2001; Mattay, J., Astruc, D., Eds.; section 2: Inorganic and Organometallic Coumpounds, Chapter 4, pp 714-803.
45. For improved detailed experimental procedure, see: Astruc, D. In Electron Transfer in Chemistry; Balzani, V., Ed.; VCH-Wiley: New York, Vol. 2, 2001; Mattay, J., Astruc, D., Eds.; section 2: Inorganic and Organometallic Coumpounds, Chapter 4, pp 714-803.
46. +-induced nucleophilic aromatic substitution, see: Astruc, D. Top. Curr. Chem. 1991, 160, 47-95.
47. +-induced nucleophilic aromatic substitution, see: Astruc, D. Top. Curr. Chem. 1991, 160, 47-95.
48. Moulines, F.; Djakovitch, L.; Boese, R.; Gloaguen, B.; Thiel, W.; Fillaut, J.-L.; Delville, M.-H.; Astruc, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 1075-1077.
49. Lewis, L. N. J. Am. Chem. Soc. 1990, 112, 5998-6004.
50. Schröder, M. Chem. Rev. 1980, 80, 187-227.