Synthesis of cationic water-soluble light-harvesting dendrimers

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1907-1910

  Wang, Shu ^a   Hong, Janice W ^b   Bazan, Guillermo C ^b  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; DENDRIMER; DIOXANE; DOUBLE STRANDED DNA; ESTER DERIVATIVE; FLUORENE DERIVATIVE; FLUORESCEIN; PHENYLENEBIS(FLUORENE); PHENYLENEFLUORENE; POLYAMIDOMINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL LABELING; COMMERCIAL PHENOMENA; FLUORESCENCE RESONANCE ENERGY TRANSFER; OPTICS; PRECURSOR; QUANTUM YIELD; SOLUBILITY; SYNTHESIS;

DNA; FLUORESCEIN; FLUORESCENCE RESONANCE ENERGY TRANSFER; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; POLYAMINES; SOLVENTS; WATER;

EID: 19544383613     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047674p     Document Type: Article

References (27)

1. (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
2. (b) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665.
3. (c) Ballauff, M. Top. Curr. Chem. 2001, 212, 177.
4. (d) Fréchet, J. M. J.; Tomalia, D. A. Dendrimers and Other Dendritic Polymers; Wiley: New York, 2001.
5. (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons; Wiley-VCH: Weinheim, Germany, 2001.
6. (b) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 1422.
7. (c) Balzani, V.; Campagna, S.; Denti, G.; Juris, A.; Serroni, S.; Venturi, M. Acc. Chem. Res. 1998, 31, 26.
8. (d) Maus, M.; De, R.; Lor, M.; Weil, T.; Mitra, S.; Wiesler, U.-M.; Herrmann, A.; Hofkens, J.; Vosch, T.; Müllen, K.; De Schryver, F. C. J. Am. Chem. Soc. 2001, 123, 7668.
9. (e) Devadoss, C.; Bharathi, P.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9635.
10. (f) Yeow, E. K. L.; Ghiggino, K. P.; Reek, J. N. H.; Crossley, M. J.; Bosman, A. W.; Schenning, A. P. H. J.; Meijer, E. W. J. Phys. Chem. B 2000, 104, 2596.
11. (a) Adronov, A.; Fréchet, J. M. J. Chem. Commun. 2000, 1701.
12. (b) Schenning, A. P. H. J.; Peeters, E.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 4489.
13. (c) Hahn, U.; Gorka, M.; Vögtle, F.; Vicinelli, V.; Ceroni, P.; Maestri, M.; Balzani, V. Angew. Chem., Int. Ed. 2002, 41, 3595.
14. (d) Balzani, V.; Ceroni, P.; Gestermann, S.; Kauffmann, C.; Gorka, M.; Vögtle, F. Chem. Commun. 2000, 853.
15. Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10954.
16. (a) Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. J. Am. Chem. Soc. 2003, 125, 896.
17. (b) Wang, S.; Bazan, G. C. Adv. Mater. 2003, 15, 1425.
18. (c) Wang, S.; Gaylord, B. S.; Bazan, G. C. J. Am. Chem. Soc. 2004, 126, 5446.
19. (d) Wang, S.; Liu, B.; Gaylord, B. S.; Bazan, G. C. Adv. Funct. Mater. 2003, 13, 463.
20. (e) Liu, B.; Gaylord, B. S.; Wang, S.; Bazan, G. C. J. Am. Chem. Soc. 2003, 125, 6705.
21. Pinto, M. R.; Schanze, K. S. Synthesis 2002, 1293.
22. Liu, B.; Wang, S.; Bazan, G. C.; Mikhailovsky, A. J. Am. Chem. Soc. 2003, 125, 13306.
23. Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117.
24. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
25. Although the ε/OU was not evaluated for the Boc-protected dendrimers, previous work has shown that interchromophoric coupling exists with other organic-soluble dendrimers. See ref 3b.
26. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum Publishers: New York, 1999.
27. The "antenna effect" arises from a larger ε and a higher binding constant due to multivalency of the higher generation dendrimers.