Molecular batteries: Ferrocenylsilylation of dendrons, dendritic cores, and dendrimers: New convergent and divergent routes to ferrocenyl dendrimers with stable redox activity

Chemistry - A European Journal

Volumn 6, Issue 14, 2000, Pages 2544-2553

  Nlate, Sylvain ^a   Ruiz, Jaime ^a   Sartor, Valérie ^a   Navarro, Reyes ^a   Blais, Jean Claude ^b   Astruc, Didier ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

Dendrimers; Electrochemistry; Electron transfer; Hydrosilylations; Metallocenes

Indexed keywords

DENDRIMER; ETHER; FERROCENE DERIVATIVE; FERROCENYLDIMETHYLSILANE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ELECTROCHEMISTRY; MOSSBAUER SPECTROSCOPY; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034679502     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000717)6:14<2544::AID-CHEM2544>3.0.CO;2-J     Document Type: Article

References (76)

1. D. Astruc, Electron Transfer and Radical Processes in Transition Metal Chemistry, VCH, New York, 1995, ch. 4: Molecular Electronics.
2. a) D. A. Tomalia, A. N. Naylor, W. A. Goddard III, Angew. Chem. 1990, 102, 119; Angew. Chem. Int. Ed. Engl. 1990, 29, 138;
3. a) D. A. Tomalia, A. N. Naylor, W. A. Goddard III, Angew. Chem. 1990, 102, 119; Angew. Chem. Int. Ed. Engl. 1990, 29, 138;
4. b) D. A. Tomalia, H. Dupont Durst in Topics Curr. Chem. Vol. 165, Supramolecular Chemistry, Directed Synthesis and Molecular Recognition (Ed.: E. Weber), Springer, Berlin, 1993, p. 193.
5. a) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules: Concepts, Syntheses and Perspectives, VCH, New York, 1996;
6. b) Advances in Dendritic Macromolecules, Vol. 1, 1994; Vol. 2, 1995; Vol. 3, 1996; Vol. 4, 1999 (Ed.: G. Newkome), JAI, Greenwich, CT;
7. b) Advances in Dendritic Macromolecules, Vol. 1, 1994; Vol. 2, 1995; Vol. 3, 1996; Vol. 4, 1999 (Ed.: G. Newkome), JAI, Greenwich, CT;
8. b) Advances in Dendritic Macromolecules, Vol. 1, 1994; Vol. 2, 1995; Vol. 3, 1996; Vol. 4, 1999 (Ed.: G. Newkome), JAI, Greenwich, CT;
9. b) Advances in Dendritic Macromolecules, Vol. 1, 1994; Vol. 2, 1995; Vol. 3, 1996; Vol. 4, 1999 (Ed.: G. Newkome), JAI, Greenwich, CT;
10. c) G. R. Newkome, E. He, C. N. Moorefield, Chem. Rev. 1999, 99, 1689.
11. N. Ardoin, D. Astruc, Bull. Soc. Chim. 1995, 132, 875.
12. a) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni, M. Venturi, Acc. Chem. Res. 1998, 31, 26;
13. b) M. Venturi, A. Credi, V. Balzani, Coord. Chem. Rev. 1999, 185-186, 233.
14. A. W. Bosman, H. M. Janssen, E. W. Meijers, Chem. Rev. 1999, 99, 1665.
15. a) M. A. Hearshaw, J. R. Moss, Chem. Commun. 1999, 1;
16. b) M. A. Hearshaw, J. R. Moss, Advan. Macromolecules, Vol. 4 (Ed.: G. Newkome), JAI, Stamford, CT, 1999, pp. 1-60.
17. a) C. Gorman, Adv. Mater. 1998, 10, 295.
18. a) S. Achar, R. J. Puddephatt, Angew. Chem. 1994, 106, 895; Angew. Chem. Int. Ed. Engl. 1994, 33, 847;
19. a) S. Achar, R. J. Puddephatt, Angew. Chem. 1994, 106, 895; Angew. Chem. Int. Ed. Engl. 1994, 33, 847;
20. b) S. Achar, R. J. Puddephatt, J. Chem. Soc. Chem. Commun. 1994, 1895.
21. E. C. Constable, Chem. Commun. 1997, 1073.
22. a) I. Cuadrado, M. Morán, J. Losada, C. M. Casado, C. Pascual, B. Alonso, G. Lobete in Advances in Dendritic Macromolecules, Vol. 3 (Ed.: G. Newkome), JAI, Greenwich, CT, 1996, pp. 151-195;
23. b) C. M. Casado, I. Cuadrado, M. Morán, B. Alonso, B. Garcia, B. Gonzalès, J. Losada, Coord. Chem. Rev. 1999, 185-186, 53.
24. For recent reviews on various aspects of ferrocenyl chemistry, see: Ferrocenes (Eds.: A. Togni, T. Hayashi), VCH-Wiley, Weinheim, 1995.
25. a) M. R. Bryce, W. Devonport, A. J. Moore, Angew. Chem. 1994, 106, 1862; Angew. Chem. Int. Ed. Engl. 1994, 33, 1761;
26. a) M. R. Bryce, W. Devonport, A. J. Moore, Angew. Chem. 1994, 106, 1862; Angew. Chem. Int. Ed. Engl. 1994, 33, 1761;
27. b) M. R. Bryce, W. Devonport in Advances in Dendritic Macromolecules, Vol. 3 (Ed.: G. R. Newkome), JAI, Greenwich, CT, 1996, pp. 115-149;
28. M. R. Bryce, W. Devonport, L. M. Goldenberg, C. Whang, Chem. Commun. 1998, 945.
29. a) G. J. Marshallsay, T. K. Hansen, A. J. Moore, M. R. Bryce, J. Becher, Synthesis 1994, 926;
30. b) J. Lau, O. Simonsen, J. Becher, Synthesis 1994, 521.
31. C. M. Cardona, A. E. Kaifer, J. Am. Chem. Soc. 1998, 120, 4023.
32. a) B. Alonso, I. Cuadrado, M. Morán, J. Losada, J. Chem. Soc. Chem. Commun. 1994, 2575;
33. b) B. Alonso, M. Morán, C. M. Casado, F. Lobete, J. Losada, I. Cuadrado, Chem. Mater. 1995, 7, 1440;
34. c) I. Cuadrado, C. M. Casado, B. Alonso, M. Morán, J. Losada, V. Belsky, J. Am. Chem. Soc. 1997, 119, 7613;
35. d) I. Cuadrado, M. Morán, C. M. Casado, B. Alonso, F. Lobete, R. Garcia, M. Ibisate, J. Losada, Organometallics 1996, 15, 5278;
36. e) T. Takada, D. J. Diaz, H. D. Abruna, I. Cuadrado, C. Casado, B. Alonso, M. Morán, J. Losada, J. Am. Chem. Soc. 1997, 119, 10763;
37. f) J. Losada, I. Cuadrado, M. Morán, C. M. Casado, B. Alonso, M. Barranco, Anal. Chim. Acta 1997, 338, 191.
38. P. Jutzi, C. Batz, B. Neumann, H. G. Stammler, Angew. Chem. 1996, 108, 2272; Angew. Chem. Int. Engl. 1996, 35, 2118.
39. P. Jutzi, C. Batz, B. Neumann, H. G. Stammler, Angew. Chem. 1996, 108, 2272; Angew. Chem. Int. Engl. 1996, 35, 2118.
40. C. Köllner, B. Pugin, A. Togni, J. Am. Chem. Soc. 1998, 120, 10274.
41. C. F. Shu, H. M. Shen, J. Mater. Chem. 1997, 7, 47.
42. G. E. Oosterom, R. J. van Haaren, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Chem. Commun. 1999, 1119.
43. R. Deschenaux, E. Serrano, A. M. Levelut, Chem. Commun. 1997, 36, 2314.
44. a) C. Valério, J.-L. Fillaut, J. Ruiz, J. Guittard, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 1997, 119, 2588;
45. b) C. Valério, E. Alonso, J. Ruiz, J.-C. Blais, D. Astruc, Angew. Chem. 1999, 111,1855; Angew. Chem. Int. Ed. 1999, 38, 1747;
46. b) C. Valério, E. Alonso, J. Ruiz, J.-C. Blais, D. Astruc, Angew. Chem. 1999, 111,1855; Angew. Chem. Int. Ed. 1999, 38, 1747;
47. c) E. Alonso, A. Labande, L. Raehm, J.-M. Kern, D. Astruc, C. R. Acad. Sci., Série IIc, Paris 1999, 2, 209;
48. d) V. Sartor, L. Djakovitch, J.-L. Fillaut, F. Moulines, F. Neveu, V. Marvaud, J. Guittard, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 1999, 121, 2929;
49. e) S. Nlate, J. Ruiz, J.-C. Blais, D. Astruc, Chem. Commun. 2000, 417.
50. S Achar, C. E. Immos, M. G. Hill, V. J. Catalano, Inorg. Chem. 1997, 36, 2314.
51. K. H. Pannel, H. Sharma, Organometallics 1991, 10, 954.
52. a) D. Seyferth, D. Y. Son, A. L. Rheingold, R. L. Ostrander, Organometallics 1994, 13, 2682;
53. b) S. W. Krska, D. Seyferth, J. Am. Chem. Soc. 1998, 120, 3604.
54. For a review of dendrimers based on main group elements, see: J. P. Majorai, A.-M. Caminade, Chem. Rev. 1999, 99, 845.
55. a) B. Marciniec, in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, ch. 2.6;
56. b) L. N. Lewis, J. Stein, K. A. Smith in Progress in Organosilicon Chemistry (Eds.: B. Marciniec, J. Chojnowski), Gordon and Breach, Langhorne, USA, 1995, p. 263.
57. a) P. J. Dandliker, F. Diederich, M. Gross, B. Knobler, A. Louati, E. M. Stanford, Angew. Chem. 1994, 106, 1821; Angew. Chem. Int. Ed. Engl. 1994, 33, 1739;
58. a) P. J. Dandliker, F. Diederich, M. Gross, B. Knobler, A. Louati, E. M. Stanford, Angew. Chem. 1994, 106, 1821; Angew. Chem. Int. Ed. Engl. 1994, 33, 1739;
59. b) G. R. Newkome, R. Güther, C. N. Moorefield, F. Cardullo, L. Echegoyen, F. Pérez-Cordero, H. Luftmann, Angew. Chem. 1995, 107, 2159; Angew. Chem. Int. Ed. Engl. 1995, 34, 2023;
60. b) G. R. Newkome, R. Güther, C. N. Moorefield, F. Cardullo, L. Echegoyen, F. Pérez-Cordero, H. Luftmann, Angew. Chem. 1995, 107, 2159; Angew. Chem. Int. Ed. Engl. 1995, 34, 2023;
61. c) H.-F. Chow, I. Y.-K. Chan, D. T. W. Chan, R. W. M. Kwok, Chem. Eur. J. 1996, 2, 1085;
62. d) P. J. Dandliker, F. Diederich, H.-F. Chow, I. Y.-K. Chan, R. W. M. Kwok, Chem. Eur. J. 1996, 2, 1085;
63. e) J. Issberner, F. Vögtle, L. De Cola, V. Balzani, Chem. Eur. J. 1997, 3, 706;
64. f) C. B. Gorman, B. L. Parkhurst, W. Y. Su, K. Y. Chen, J. Am. Chem. Soc. 1997, 119, 1141;
65. g) D. K. Smith, F. Diederich, Chem. Eur. J. 1998, 4, 2353.
66. a) J. B. Flanagan, S. Margel, A. J. Bard, F. C. Anson, J. Am. Chem. Soc. 1978, 100, 4248;
67. b) F. Moulines, L. Djakovitch, R. Boese, B. Gloaguen, W. Thiel, J.-L. Fillaut, M.-H. Delville, D. Astruc, Angew. Chem. 1993, 105, 1132; Angew. Chem. Int. Ed. Engl. 1993, 32, 1075;
68. b) F. Moulines, L. Djakovitch, R. Boese, B. Gloaguen, W. Thiel, J.-L. Fillaut, M.-H. Delville, D. Astruc, Angew. Chem. 1993, 105, 1132; Angew. Chem. Int. Ed. Engl. 1993, 32, 1075;
69. c) J. Ruiz, D. Astruc, C. R. Acad. Sci., Série IIc, Paris 1998, 21.
70. R. Murray in Molecular Design of Electrode Surfaces (Ed.: R. Murray), Wiley, New York, 1992, p. 1.
71. R. L. Collins, J. Chem. Phys. 1965, 42, 1072.
72. a) A. Archut, F. Vögtle, L. De Cola, G. C. Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699;
73. b) P. Lange, A. Schier, H. Schmidbauer, Inorg. Chem. 1996, 35, 637.
74. a) S. J. Green, J. J. Pietron, J. J. Stokes, M. J. Hostetler, H. Vu, W. P. Wuelfing, R. W. Murray, Langmuir 1998, 14, 5612;
75. b) C. B. Gorman, J. C. Smith, M. W. Hager, B. L. Parhurst, H. Sierzputowska-Gracz, C. A. Haney, J. Am. Chem. Soc. 1999, 121, 9958;
76. c) C. A. Christensen, L. M. Goldenberg, M. R. Bryce, J. Becher, Chem. Commun. 1998, 509.