Controllable, selective per-functionalization of dendritic oligoamines

Organic Letters

Volumn 6, Issue 7, 2004, Pages 1075-1078

  Vögtle, Fritz ^a   Fakhrnabavi, Hassan ^a   Lukin, Oleg ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BASE; CHLORIDE; DENDRIMER; SULFUR;

ANALYTIC METHOD; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; TEMPERATURE;

EID: 2342652775     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030130n     Document Type: Article

References (50)

1. (a) Definitions of dendrimers, dendrons, and branched polymers were discussed by numerous experts during the 3rd International Dendrimer Symposium, September 17-20, Berlin, Germany. The term "dendritic molecules" seems to be suitable for all types of branched species.
2. (b) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1996.
3. (c) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications; Wiley-VCH: New York, 2001.
4. Dendrimers and Other Dendritic Polymers; Frechet, J. M. J., Tomalia, D. A., Eds.; Wiley: New York, 2001.
5. (a) Schlüter, A. D.; Rabe, J. P. Angew. Chem. 2000, 112, 860-880; Angew. Chem., Int. Ed. 2000, 39, 864-883.
6. (a) Schlüter, A. D.; Rabe, J. P. Angew. Chem. 2000, 112, 860-880; Angew. Chem., Int. Ed. 2000, 39, 864-883.
7. (b) Encyclopedia of Polymer Science and Technology, 3rd ed.; Kroschwitz, J., Ed.; Wiley: New York, 2001.
8. (c) Sheiko, S. S.; Möller, M. Top. Curr. Chem. 2001, 212, 138.
9. (d) Muscat, D.; van Benthem, R. A. T. M. Top. Curr. Chem. 2001, 212, 41.
10. Krause, W.; Hackmann-Schlichter, N.; Maier, F. K.; Müller, R. Top. Curr. Chem. 2000, 210, 261.
11. (a) Platzek, J. Lecture at the 3rd International Dendrimer Symposium, September 17-20, 2003, Berlin, Germany,
12. (b) Schering AG patents: EP 430863, WO 97/02051, WO 98/24775, WO 98/24774, US 5911971.
13. (a) Dennig, J. Top. Curr. Chem. 2003, 228, 227-236.
14. (b) Joester, D.; Walter, E.; Losson, M.; Pugin, R.; Merkle, H. P.; Diederich, F. Angew. Chem. 2003, 115, 1524-1528;
15. Angew. Chem., Int. Ed. 2003, 42, 1486-1490.
16. (a) Yamaguchi, H.; Harada, A. Top. Curr. Chem. 2001, 228, 237-258.
17. (b) Quintana, A.; Raczka, E.; Piehler, L.; Lee, I.; Myc, A.; Majoros, I.; Patri, A. K.; Thomas, T.; Mule, J.; Baker, J. R., Jr. Pharmaceut. Res. 2002, 19, 1310-1316.
18. Grinstaff, M. W. Chem. Eur. J. 2002, 8, 2838-2846.
19. (a) Brettreich, M.; Burghart, S.; Böttcher, C.; Bayerl, T.; Hirsch, A. Angew. Chem. 2000, 112, 1915-1918; Angew. Chem., Int. Ed. 2000, 39, 1845-1848.
20. (a) Brettreich, M.; Burghart, S.; Böttcher, C.; Bayerl, T.; Hirsch, A. Angew. Chem. 2000, 112, 1915-1918; Angew. Chem., Int. Ed. 2000, 39, 1845-1848.
21. (b) Nierengarten, J.-F. Top. Curr. Chem. 2003, 228, 87-110.
22. (c) Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Jayaraman, N.; Nepogodiev, S. A.; Stoddart J. F. Chem. Eur. J. 1996, 2, 1115-1128.
23. (d) Lindhorst, T. K. Top. Curr. Chem. 2002, 218, 201-235.
24. (e) Vosch, T.; Hofkens, J.; Cotlet, M.; Köhn, F.; Fujiwara, H.; Gronheid, R.; Van Der Biest, K.; Weil, T.; Herrmann, A.; Müllen, K.; Mukamel, S.; Van der Auweraer, M.; De Schryver, F. C. Angew. Chem. 2001, 113, 4779-4784; Angew. Chem., Int. Ed. 2001, 40, 4643-4648.
25. (e) Vosch, T.; Hofkens, J.; Cotlet, M.; Köhn, F.; Fujiwara, H.; Gronheid, R.; Van Der Biest, K.; Weil, T.; Herrmann, A.; Müllen, K.; Mukamel, S.; Van der Auweraer, M.; De Schryver, F. C. Angew. Chem. 2001, 113, 4779-4784; Angew. Chem., Int. Ed. 2001, 40, 4643-4648.
26. (f) Devadoss, C.; Bharathi, P.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9635-9644.
27. (g) Choi, M.-S.; Aida, T.; Luo, H.; Araki, Y.; Ito, O. Angew. Chem. 2003, 115, 4194-4197; Angew. Chem., Int. Ed. 2003, 42, 4060-4063.
28. (g) Choi, M.-S.; Aida, T.; Luo, H.; Araki, Y.; Ito, O. Angew. Chem. 2003, 115, 4194-4197; Angew. Chem., Int. Ed. 2003, 42, 4060-4063.
29. (h) Hirsch, A. Lecture at 3rd International Dendrimer Symposium, September 17-20, 2003, Berlin, Germany,
30. (i) Ferguson, G.; Gallagher, J. F.; McKervey, M. A.; Madigan, E. J. Chem. Soc., Perkin Trans. 1 1996, 599-602.
31. (j) Recker, J.; Müller, W. M.; Müller, U.; Kubota, T.; Okamoto, Y.; Nieger, M.; Vögtle, F. Chem. Eur. J. 2002, 8, 4434-4442.
32. (a) Hawker, C.; Fréchet, J. M. J. Chem. Comm. 1990, 1010-1013.
33. (b) Wooley, K. L.; Hawker, C.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4252-4261.
34. (c) Miller, T. M.; Neenan, T. X. Chem. Mater. 1990, 2, 346-349.
35. (d) Chapter 5 in ref 1c.
36. de Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem. 1993, 105, 1370-1373; Angew. Chem., Int. Ed. 1993, 32, 1308-1311.
37. de Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem. 1993, 105, 1370-1373; Angew. Chem., Int. Ed. 1993, 32, 1308-1311.
38. Tomalia, D. A.; Backer, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466-2468.
39. (a) Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 155-158.
40. (b) Wörner, C.; Mühlhaupt, R. Angew. Chem. 1993, 105, 1367-1369; Angew. Chem. Int. Ed. 1993, 32, 1306-1308.
41. (b) Wörner, C.; Mühlhaupt, R. Angew. Chem. 1993, 105, 1367-1369; Angew. Chem. Int. Ed. 1993, 32, 1306-1308.
42. Baars, M. W. P. L.; Karlsson, A. J.; Sorokin, V.; de Waal, B. F. W.; Meijer, E. W. Angew. Chem. 2000, 112, 4432-4436; Angew. Chem., Int. Ed. 2000, 39, 4262-4266.
43. Baars, M. W. P. L.; Karlsson, A. J.; Sorokin, V.; de Waal, B. F. W.; Meijer, E. W. Angew. Chem. 2000, 112, 4432-4436; Angew. Chem., Int. Ed. 2000, 39, 4262-4266.
44. (a) Stephan, H.; Spies, H.; Johannsen, B.; Kauffmann, C.; Vögtle. F. Org. Lett. 2000, 2, 2343-2346.
45. (b) Ballester, P.; Gomila, R. M.; Hunter, C. A.; King, A. S. H.; Twyman, L. J. Chem. Commun. 2003, 38-39.
46. Nomenclature of 1→n branching was suggested by G. R. Newkome. See ref 1b,c for details.
47. (a) Archut, A.; Gestermann, S.; Hesse, R.; Kauffmann, C.; Vögtle, F. Synlett, 1998, 546-548.
48. (b) Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987-1041.
49. For dumbbell-shaped dendritic species, see: (a) Newkome, G. R.; Baker, G. R.; Saunders, M. J.; Russo, P. S.; Gupta, V. K.; Yao, Z.; Miller, J. E.; Bouillion, K. J. Chem. Soc., Chem. Commun. 1996, 752-753. (b) Mller, L. L.; Zinger, B.; Schlechte, J. S. Chem. Mater. 1999, 11, 2313-2315.
50. For dumbbell-shaped dendritic species, see: (a) Newkome, G. R.; Baker, G. R.; Saunders, M. J.; Russo, P. S.; Gupta, V. K.; Yao, Z.; Miller, J. E.; Bouillion, K. J. Chem. Soc., Chem. Commun. 1996, 752-753. (b) Mller, L. L.; Zinger, B.; Schlechte, J. S. Chem. Mater. 1999, 11, 2313-2315.