Positive dendritic effects on the electron-donating potencies of poly(propylene imine) dendrimers

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1287-1290

  Ong, Winston ^a   McCarley, Robin L ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7,7,8,8 TETRACYANOQUINODIMETHANE; BENZYL DERIVATIVE; DENDRIMER; METHANE; POLY(PROPYLENE IMINE); POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON TRANSPORT; OXIDATION REDUCTION POTENTIAL; REACTION ANALYSIS; SYNTHESIS;

EID: 17444417127     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0500564     Document Type: Article

References (19)

1. Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 885.
2. (a) Hawker, C.; Frechét, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
3. (b) Newkome, G. R.; Weis, C. D.; Childs, B. J. Des. Monomers Polym. 1998, 1, 3.
4. For reviews, see: (a) Grayson, S. M.; Frechét, J. M. J. Chem. Rev. 2001, 101, 3819. (b) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 38, 885.
5. For reviews, see: (a) Grayson, S. M.; Frechét, J. M. J. Chem. Rev. 2001, 101, 3819. (b) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 38, 885.
6. For recent examples, see: (a) Ornatska, M.; Bergman, K. N.; Rybak, B.; Peleshanko, S.; Tsukruk, V. V. Angew. Chem., Int. Ed. 2004, 43, 5246. (b) Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2004, 126, 1604.
7. For recent examples, see: (a) Ornatska, M.; Bergman, K. N.; Rybak, B.; Peleshanko, S.; Tsukruk, V. V. Angew. Chem., Int. Ed. 2004, 43, 5246. (b) Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2004, 126, 1604.
8. 6 we did not encounter this situation.
9. See Supporting Information for details.
10. This is commonly observed with other symmetric-type dendrimers terminated with multiple redox sites. For example, see: Casado, C. M.; Cuadrado, I.; Morán, M.; Alonso, B.; García, B.; González, B.; Losada, J. Coord. Chem. Rev. 1999, 185-186, 53.
11. Jansen, J. F. G. A.; de Brabander-van den Berg, E. M. M.; Meijer, E. W. Science 1994, 265, 1226.
12. -, see: Jones, M. T.; Hertler, W. R. J. Am. Chem. Soc. 1964, 86, 1881.
13. Dendrimers in the amide and urea series contain two thermodynamically distinct types of donors (interior PPI amines and 4-DMAB units) that can compete for CT interactions with TCNQ.
14. We could not fit the corrected absorption changes into the standard decay forms. Thus, the profiles in Figure 3 are arbitrarily plotted in the first-order form for ease of comparison.
15. Even though the effective [4-DMAB] has been constrained, the total number of donor groups (4-DMAB and interior tertiary amines) still slightly varies between generations but not to a significant extent. See ref 14 for details.
16. For recent examples of positive dendritic effects, see: (a) Delort, E.; Darbre, T.; Reymond, J. L. J. Am. Chem. Soc. 2004, 126, 15642. (b) Dahan, A.; Portnoy, M. Org. Lett. 2003, 5, 1197.
17. For recent examples of positive dendritic effects, see: (a) Delort, E.; Darbre, T.; Reymond, J. L. J. Am. Chem. Soc. 2004, 126, 15642. (b) Dahan, A.; Portnoy, M. Org. Lett. 2003, 5, 1197.
18. One must realize that the total number of donor sites for the dendrimers in the (4-DMAB)-terminated series is almost doubled relative to those in the control series. As an example, the theoretical number of donor sites in the amide series 1a-5a, ordered as 4-DMAB and interior tertiary amine units, respectively, is as follows: 1a, 4 and 2; 2a, 8 and 6; 3a, 16 and 14; 4a, 32 and 30; 5a, 64 and 62.
19. 2- formation.