Multiredox heterometallic carbosilane dendrimers

Organometallics

Volumn 26, Issue 21, 2007, Pages 5153-5164

  Zamora, Magdalena ^a   Alonso, Beatriz ^a   Pastor, César ^a   Cuadrado, Isabel ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRODES; FUNCTIONAL GROUPS; HYDROSILYLATION; OXIDATION; PLATINUM; SILANES; SILICON; X RAY DIFFRACTION;

CARBOSILANE; FERROCENYL UNITS; HETEROMETALLICS; IRON CENTERS;

DENDRIMERS;

EID: 35348993838     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700559t     Document Type: Article

References (63)

1. See for example: (a) Newkome, G. R., Moorefield, C. N., Vögtle, T., Eds.; Dendrimers and Dendrons: Concept, Syntheses and Applications; Wiley-VCH Verlag: Weinheim, Germany, 2001.
2. (b) Frechét, J. M. J., Tomalia, D. A., Eds.; Dendrimers and Other Dendritic Polymers; VCH: Weinheim, Germany, 2002.
3. (c) Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987.
4. (d) Tomalia, D. A. Prog. Polym. Sci. 2005, 30, 294.
5. For metallodendrimers, see for example: (a) Newkome, G. R.; Moorefield, C. N. Chem. Rev. 1999, 99 1689.
6. (b) Gorman, C. Adv. Mater. 1998, 10, 295.
7. (b) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845.
8. (c) Metal-Containing and Metallosupramolecular Polymers and Materials; Schubert, U. S., Newkome, G. R., Manners, I., Eds.; Oxford University Press: London, 2006.
9. (d) Mery, D.; Astruc, D. Coord. Chem. Rev. 2006, 250, 1965.
10. (e) Berger, A.; Gebbink, R. J. M.; van Koten, G. Top. Organomet. Chem. 2006, 20, 1.
11. (f) Newkome, G. R. In Frontiers in Transition Metal-Containing Polymers; Abd-El-Aziz, A. S. A, Manners, I., Eds.; Wiley: Hoboken, NJ, 2007; Chapter 10.
12. For reviews on organometallic dendrimers, see for example: (a) Cuadrado, I.; Moran, M.; Casado, C. M.; Alonso, B.; Losada, J. Coord. Chem. Rev. 1999, 193-195, 395.
13. (b) Hearshaw, M. A.; Moss, J. R. Chem. Commun. 1999, 1.
14. (c) Rossell, O.; Seco, M.; Angurell, I. C. R. Chim. 2003, 6, 805.
15. (d) Chase, P. A.; van Koten, G. J. Organomet. Chem. 2004, 689, 4016.
16. (e) Manners, I. In Synthetic Metal-Containing Polymers; Manners, I., Ed.; Wiley-VCH: Weinheim, 2004; p 237.
17. (f) Astruc, D. In Frontiers in Transition Metal-Containing Polymers; Abd-El-Aziz, A. S. A., Manners, I., Eds.; Wiley: Hoboken, NJ, 2007; Chapter 11.
18. (a) Angurell, I.; Rossell, O.; Seco, M.; Ruiz, E. Organometallics 2005, 24, 6365.
19. (b) Angurell, I.; Lima, J. C.; Rodriguez, L.-I.; Rossell, O.; Seco, M. New J. Chem. 2006, 30, 1004.
20. Méry, D.; Plault, L.; Orneias, C.; Ruiz, J.; Nlate, S.; Astruc, D.; Blais, J.-C.; Rodrigues, J.; Stéphane, C.; Kiracki, K.; Perrin, C. Inorg. Chem. 2006, 45, 1156.
21. Casado, C. M.; González, B.; Cuadrado, I.; Alonso, B.; Morán, M.; Losada, J. Angew. Chem., Int. Ed. 2000, 39, 2135.
22. Achar, S.; Immoos, C. E.; Hill, M. G.; Catalano, V. J. Inorg. Chem. 1997, 36, 2314.
23. Liu, G. X.; Puddephatt, R. J. Organometallics 1996, 15, 5257.
24. Juris, A.; Balzani, V.; Campagna, S.; Denti, G.; Serroni, S.; Frei, G.; Guedel, H. U. Inorg. Chem. 1994, 33, 1491.
25. (a) Supramolecular Electrochemistry; Kaifer, A. E., Gómez-Kaifer, M., Eds.; Wiley-VCH: Weinheim: Germany, 1999; Chapter 16, p 207.
26. (b) Inorganic Electrochemistry. Theory, Practice and Application; Zanello, P., Ed.; Royal Society of Chemistry: Cambridge, 2003; Chapter 5, p 185.
27. (c) Astruc, D.; Daniel, M. C.; Nlate, S.; Ruiz, J. In Trends in Molecular Electrochemistry; Pombeiro, A. J. L., Amatore, C., Eds.; Marcel Dekker: New York, 2004; Chapter 9, p 283.
28. Alonso, B.; García-Armada, P.; Losada, J.; Cuadrado, I.; González, B.; Casado, C. M. Biosens. Bioelectron. 2004, 19, 1617.
29. (a) Cuadrado, I.; Moran, M.; Casado, C. M.; Alonso, B.; Lobete, F.; García, B.; Ibisate, M.; Losada, J. Organometallics 1996, 15, 5278.
30. (b) Gonzalez, B.; Casado, C. M.; Alonso, B.; Cuadrado, I.; Moran, M.; Wang, Y.; Kaifer, A. E. Chem. Commun. 1998, 2569.
31. (c) Zamora, M.; Herrero, S.; Losada, J.; Cuadrado, I.; Casado, C. M.; Alonso, B. Organometallics 2007, 26, 2688.
32. (a) Alonso, B.; Cuadrado, I.; Moran, M.; Losada, J. J. Chem. Soc., Chem. Commun. 1994, 2575.
33. (b) Alonso, B; Morán, M; Casado, C. M.; Lobete, F.; Losada, J.; Cuadrado, I. Chem. Mater. 1995, 7, 1440.
34. (c) García, B.; Casado, C. M.; Cuadrado, I.; Alonso, B.; Moran, M.; Losada, J. Organometallics 1999, 18, 2349.
35. Cuadrado, I.; Casado, C. M.; Alonso, B.; Morán, M.; Losada, J.; Belsky, V. J. Am. Chem. Soc. 1997, 119, 7613.
36. Alonso, B.; González, B.; Ramírez, E.; Zamora, M.; Casado, C. M.; Cuadrado, I. J. Organomet. Chem. 2001, 637-639, 642.
37. (a) Hawker, C. J.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1990, 1010.
38. (b) Hawker, C. J.; Frechet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
39. For an excellent recent review on convergent construction of dendrimers see: Grayson, S. K.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819.
40. Zamora, M. Ph.D. Thesis, Universidad Autónoma de Madrid, 2006.
41. Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502.
42. (a) Comprehensive Handbook on Hydrosilylation; Marciniec, B., Ed.; Pergamon Press: Oxford, 1992.
43. (b) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1989; Part 2, p 1479.
44. Davis, R.; Kane-Maguire, L.A. P. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, England, 1982; Vol. 3, pp 1001-54.
45. See for example: (a) Santi, S.; Ceccon, A.; Bisello, A.; Durante, C.; Ganis, P.; Orian, L. Organometallics 2005, 24, 4691.
46. (b) Gomes, E. L. S.; Hörner, M.; Young, V. G., Jr.; Dupont, J.; Caliman, V.; Casagrande, O. L., Jr. Organometallics 1999, 18, 3869.
47. (c) Müller, T. J. J.; Blümel, J. J. Organomet. Chem. 2003, 683, 354.
48. It is well-known that electron-withdrawing substituents on the vinyl group decrease the rate of hydrosilylation processes compared to the more electron-donating groups. On the other hand, steric factors due to substituents in both silane and vinyl groups may also affect the rate and completeness of hydrosilylation reactions. See, for example, refs 20, 24, and 25.
49. (a) Stein, J.; Lewis, L. N.; Smith, K. A.; Lettko, K. X. J. Inorg. Organomet. Polym. 1991, 1, 325.
50. (b) Liu, H. Q.; Harrod, J. F. Can. J. Chem. 1990, 68, 1100.
51. For a recent interesting work illustrating the effect of the substituents of the Si-H and C=C groups on hydrosilylation reactions see: Hilf, S.; Cyr, P. W.; Rieder, D. A.; Manners, I.; Ishida, T.; Chujo, Y. Macromol. Rapid Commun. 2005, 26, 950.
52. Flanagan, J. B.; Margel, S.; Bard, A. J.; Anson, F. C. J. Am. Chem. Soc. 1978, 100, 4248.
53. Analytical Electrochemistry, 2 ed.; Wang, J., Ed.; Wiley-VCH: New York, 2000.
54. (a) Murray, R. W. In Molecular Design of Electrode Surfaces; Murray, R. W., Ed.; Techniques of Chemistry XXII; Wiley: New York, 1992.
55. (b) Abruña, H. D. In Electroresponsive Molecular and Polymeric Systems; Skotheim, T. A., Ed.; Dekker: New York, 1988; Vol. 1.
56. FWHM = 90.6/n (n = number of electrons transferred per molecule). See ref 28.
57. Further studies of the use of 1 and 4 in the synthesis of siloxane-based heterometallic dendritic and polymeric assemblies are in progress and will be reported.
58. Mawaziny, S. J. Chem. Soc. (A) 1970, 1641.
59. Sheldrick, G. M. SADABS Version 2.03, Program for Empirical Absorption Correction; University of Göttingen: Germany, 1997-2001.
60. SAINT+NT Version 6.04; SAX Area-Detector Integration Program; Bruker Analytical X-ray Instruments: Madison, WI, 1997-2001.
61. Bruker AXS SHELXTL Version 6.10, Structure Determination Package; Bruker Analytical X-ray Instruments: Madison, WI, 2000.
62. Sheldrick, G. M. Acta Crystallogr. A 1990, 46, 467.
63. Sheldrick, G. M. SHELXL97, Program for Crystal Structure Refinement; Germany, 1997.