Toward nanoamphiphiles: Efficient synthesis of desymmetrized polyphenylene dendrimers

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 8029-8037

  Mihov, G ^a   Scheppelmann, I ^a   Mullen K ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

METHANE; POLYPHENYLENE OXIDES; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

POLAR FUNCTIONAL GROUP; POLYPHENYLENE;

DENDRIMERS;

AMPHOPHILE; DENDRIMER; KETONE DERIVATIVE; METHANE; POLYPHENYLENE DENDRIMER; TETRAKIS(4 ETHYNYLPHENYL)METHANE; TETRAPHENYLCYCLOPENTADIENONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; MACROMOLECULE; STOICHIOMETRY; SYNTHESIS;

EID: 8644254236     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048998u     Document Type: Article

References (38)

1. Choi, S. W.; Kim, W. S.; Kim, J. H. J. Dispersion Sci. Technol. 2003, 24, 457-487.
2. Pelton, E. Chemical Reactions at the Latex-Solution Interface; Kluwer Academic Publishers: New York, 1990.
3. Gerion, D.; Pinaud, F.; Williams, S. C.; Parak, W. J.; Zanchet, D.; Weiss, S.; Alivisatos, A. P. J. Phys. Chem. B 2001, 105, 8861-8871.
4. Bruchez, M., Jr.; Moronne, M.; Gin, P.; Weiss, S.; Alivisatos, A. P. Science 1998, 281, 2013-2016.
5. Norgaard, K.; Weygand, M. J.; Kjaer, K.; Brust, M.; Bjornholm, T. Faraday Discuss. 2004, 221-233.
6. Niemeyer, C. M. Angew. Chem., Int. Ed. 2003, 42, 5796-5800.
7. Benters, R.; Niemeyer, C. M.; Wöhrle, D. ChemBioChem 2001, 2, 686-694.
8. Weil, T.; Reuther, E.; Mullen, K. Angew. Chem., Int. Ed. 2002, 41, 1900-1904.
9. Herrmann, A.; Mihov, G.; Vandermeulen, G. W. M.; Klok,. H.-A.; Müllen, K. Tetrahedron 2003, 59, 3925-3935.
10. Mihov, G.; Herrmann, A.; Prawitt, D.; Brixel, L.; Hengstler, J. G.; Müllen, K. Unpublished results.
11. Minard-Basquin, C.; Weil, T.; Hohner, A.; Radler, J. O.; Mullen, K. J. Am Chem. Soc. 2003, 125, 5832-5838.
12. Wiesler, U. M.; Weil, T.; Müllen, K. Top. Curr. Chem. 2001, 212, 1-40.
13. Wiesler, U. M.; Berresheim, A. J.; Morgenroth, F.; Lieser, G.; Müllen, K. Macromolecules 2001, 34, 187-199.
14. Morgenroth, F.; Reuther, E.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 631-634.
15. Grimsdale, A. C.; Bauer, R.; Weil, T.; Tchebotareva, N.; Wu, J.; Watson, M.; Müllen, K. Synthesis (Stuttgart) 2002, 9, 1229-1239.
16. (a) Singh, P. Bioconj. Chem. 1998, 9, 54-63.
17. (b) Froehling, P. E.; Linssen, H. A. J. Macromol. Chem. Phys. 1998, 199, 1691-1695.
18. (c) Newkome, G. R.; Childs, B. J.; Rourk, M. J.; Baker, G. R.; Moorefield, C. N. Biotechnol. Bioeng (Comb. Chem.) 1998, 61, 243-253.
19. (d) Pan, Y.; Ford, W. T. Macromolecules 2000, 33, 3731-3738.
20. (e) Sideratou, Z.; Tsiourvas, D.; Paleos, C. M. J. Colloid. Interface Sci. 2001, 242, 272-276.
21. (f) Grayson, S. M.; Fréchet, J. M. J. Org. Lett. 2002. 4, 3171-3174.
22. (g) Newkome, G. R.; Kim, H. J.; Moorefield, C. N.; Maddi, H.; Yoo, K.-S. Macromolecules 2003, 36, 4345-4354.
23. (h) Séverac, M.; Leclaire, J.; Sutra, P.; Caminade, A.-M.; Majoral, J.-P. Tetrahedron Lett. 2004, 45, 3019-3022.
24. (a) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1993, 1287-1297.
25. (b) Martin, I. K.; Twyman, L. J. Tetrahedron Lett. 2001, 42, 1119-1121.
26. (c) Grayson, S. M.; Fréchet, J. M. J. J. Am. Chem. Soc. 2000, 122, 10335-10344.
27. (d) Nierengarten, J.-F.; Eckert, J.-F.; Rio, Y.; del Pillar Carreon, M.; Gallani, J.-L.; Guillon, D. J. Am. Chem. Soc. 2001, 123, 9743-9748.
28. (e) Maraval, V.; Sebastian, R.-M.; Ben, F.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Eur. J. Inorg. Chem. 2001, 1681-1691.
29. (f) Ong, W.; Kaifer, A. E. J. Am. Chem. Soc. 2002, 124, 9358-9359.
30. (g) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496-11505.
31. Weil, T.; Wiesler, U. M.; Herrmann, A.; Bauer, R.; Hofkens, J.; De Schryver, F. C.; Mullen K. J. Am Chem. Soc. 2001, 123, 8101-8108.
32. Mihov, G.; Grebel-Koehler, D.; Lübbert, A.; Vandermeulen, G. W. M.; Klok, H.-A.; Herrmann, A.; Müllen, K. 2004, Bioconj. Chem. Submitted for publication.
33. Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987-1041 and references therein.
34. Morgan, J. R.; Cloninger, M. J. Curr. Opin. Drug Discovery Dev. 2002, 5, 966-973 and references therein.
35. Hecht, S. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1047-1058 and references therein.
36. Velonia, K.; Rowan, A. E.; Nolte, R. J. M. J. Am Chem. Soc. 2002, 124, 4224-4225.
37. Arackal, Th. J.; Eistert, B. Chem. Ber. 1975, 108, 2660-2663.
38. Weil, T. Ph.D. Thesis, 2002, University of Mainz, Germany.