Ferrocenyl-functionalized poly(propylenimine) dendrimers

Organometallics

Volumn 15, Issue 25, 1996, Pages 5278-5280

  Cuadrado, Isabel ^a   Morán, Moisés ^a   Casado, Carmen M ^a   Alonso, Beatriz ^a   Lobete, Francisco ^a   García, Belén ^a   Ibisate, Marta ^a   Losada, José ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSIDAD POLITÉCNICA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000251871     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9605948     Document Type: Article

References (35)

1. Recent reviews: (a) Newkome, G. R. Advances in Dendritic Macromolecules; JAI Press: Greenwich, CT, 1994; Vol. 1; Ibid., 1995; Vol. 2. (b) Tomalia, D. A.; Durst, H. D. In Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin, 1993; Vol. 165, p 193. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Fréchet, J. M. Science 1994, 263, 1710. (e) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
2. Recent reviews: (a) Newkome, G. R. Advances in Dendritic Macromolecules; JAI Press: Greenwich, CT, 1994; Vol. 1; Ibid., 1995; Vol. 2. (b) Tomalia, D. A.; Durst, H. D. In Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin, 1993; Vol. 165, p 193. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Fréchet, J. M. Science 1994, 263, 1710. (e) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
3. Recent reviews: (a) Newkome, G. R. Advances in Dendritic Macromolecules; JAI Press: Greenwich, CT, 1994; Vol. 1; Ibid., 1995; Vol. 2. (b) Tomalia, D. A.; Durst, H. D. In Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin, 1993; Vol. 165, p 193. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Fréchet, J. M. Science 1994, 263, 1710. (e) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
4. Recent reviews: (a) Newkome, G. R. Advances in Dendritic Macromolecules; JAI Press: Greenwich, CT, 1994; Vol. 1; Ibid., 1995; Vol. 2. (b) Tomalia, D. A.; Durst, H. D. In Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin, 1993; Vol. 165, p 193. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Fréchet, J. M. Science 1994, 263, 1710. (e) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
5. Recent reviews: (a) Newkome, G. R. Advances in Dendritic Macromolecules; JAI Press: Greenwich, CT, 1994; Vol. 1; Ibid., 1995; Vol. 2. (b) Tomalia, D. A.; Durst, H. D. In Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin, 1993; Vol. 165, p 193. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Fréchet, J. M. Science 1994, 263, 1710. (e) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
6. Recent reviews: (a) Newkome, G. R. Advances in Dendritic Macromolecules; JAI Press: Greenwich, CT, 1994; Vol. 1; Ibid., 1995; Vol. 2. (b) Tomalia, D. A.; Durst, H. D. In Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin, 1993; Vol. 165, p 193. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Fréchet, J. M. Science 1994, 263, 1710. (e) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
7. See for example: (a) Slany, M.; Bardaji, M.; Casanove, M. J.; Caminade, A.-M.; Majorai, J.-P.; Chaudret, B. J. Am. Chem. Soc. 1995, 117, 9764. (b) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 211. (c) Newkome, G. R.; Güther, R.; Moorefield, C. N.; Cardullo, F.; Echegoyen, L.; Pérez-Cordero, E.; Luftmann, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2023. (d) Lange, P.; Schier, A.; Schmidbaur, H. Inorg. Chem. 1996, 35, 637. See also ref 4.
8. See for example: (a) Slany, M.; Bardaji, M.; Casanove, M. J.; Caminade, A.-M.; Majorai, J.-P.; Chaudret, B. J. Am. Chem. Soc. 1995, 117, 9764. (b) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 211. (c) Newkome, G. R.; Güther, R.; Moorefield, C. N.; Cardullo, F.; Echegoyen, L.; Pérez-Cordero, E.; Luftmann, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2023. (d) Lange, P.; Schier, A.; Schmidbaur, H. Inorg. Chem. 1996, 35, 637. See also ref 4.
9. See for example: (a) Slany, M.; Bardaji, M.; Casanove, M. J.; Caminade, A.-M.; Majorai, J.-P.; Chaudret, B. J. Am. Chem. Soc. 1995, 117, 9764. (b) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 211. (c) Newkome, G. R.; Güther, R.; Moorefield, C. N.; Cardullo, F.; Echegoyen, L.; Pérez-Cordero, E.; Luftmann, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2023. (d) Lange, P.; Schier, A.; Schmidbaur, H. Inorg. Chem. 1996, 35, 637. See also ref 4.
10. See for example: (a) Slany, M.; Bardaji, M.; Casanove, M. J.; Caminade, A.-M.; Majorai, J.-P.; Chaudret, B. J. Am. Chem. Soc. 1995, 117, 9764. (b) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 211. (c) Newkome, G. R.; Güther, R.; Moorefield, C. N.; Cardullo, F.; Echegoyen, L.; Pérez-Cordero, E.; Luftmann, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2023. (d) Lange, P.; Schier, A.; Schmidbaur, H. Inorg. Chem. 1996, 35, 637. See also ref 4.
11. Cuadrado, I.; Morán, M.; Losada, J.; Casado, C. M.; Pascual, C.; Alonso, B.; Lobete, F. In Advances in Dendritic Macromolecules; Newkome, G. R., Ed.; JAI Press: Greenwich, CT, Vol. 3, in press.
12. For organometallic dendrimers see for example: (a) Seyferth, D.; Kugita, T.; Rheingold, A.; Yap, G. P. A. Organometallics 1995, 14, 5362. (b) Liao, Y. H.; Moss, J. R. Organometallics 1995, 14, 2130. (c) Huck, W. T. S.; van Veggel, F. C. J. M.; Kropman, B. L.; Blank, D. H. A.; Keim, E. G.; Smithers, M. M. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 8293. (d) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D.; van Koten, G. Nature 1994, 372, 659. (e) Fillaut, J.-L.; Linares, J.; Astruc, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2460. (f) Achar, S.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1994, 1895.
13. For organometallic dendrimers see for example: (a) Seyferth, D.; Kugita, T.; Rheingold, A.; Yap, G. P. A. Organometallics 1995, 14, 5362. (b) Liao, Y. H.; Moss, J. R. Organometallics 1995, 14, 2130. (c) Huck, W. T. S.; van Veggel, F. C. J. M.; Kropman, B. L.; Blank, D. H. A.; Keim, E. G.; Smithers, M. M. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 8293. (d) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D.; van Koten, G. Nature 1994, 372, 659. (e) Fillaut, J.-L.; Linares, J.; Astruc, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2460. (f) Achar, S.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1994, 1895.
14. For organometallic dendrimers see for example: (a) Seyferth, D.; Kugita, T.; Rheingold, A.; Yap, G. P. A. Organometallics 1995, 14, 5362. (b) Liao, Y. H.; Moss, J. R. Organometallics 1995, 14, 2130. (c) Huck, W. T. S.; van Veggel, F. C. J. M.; Kropman, B. L.; Blank, D. H. A.; Keim, E. G.; Smithers, M. M. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 8293. (d) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D.; van Koten, G. Nature 1994, 372, 659. (e) Fillaut, J.-L.; Linares, J.; Astruc, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2460. (f) Achar, S.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1994, 1895.
15. For organometallic dendrimers see for example: (a) Seyferth, D.; Kugita, T.; Rheingold, A.; Yap, G. P. A. Organometallics 1995, 14, 5362. (b) Liao, Y. H.; Moss, J. R. Organometallics 1995, 14, 2130. (c) Huck, W. T. S.; van Veggel, F. C. J. M.; Kropman, B. L.; Blank, D. H. A.; Keim, E. G.; Smithers, M. M. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 8293. (d) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D.; van Koten, G. Nature 1994, 372, 659. (e) Fillaut, J.-L.; Linares, J.; Astruc, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2460. (f) Achar, S.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1994, 1895.
16. For organometallic dendrimers see for example: (a) Seyferth, D.; Kugita, T.; Rheingold, A.; Yap, G. P. A. Organometallics 1995, 14, 5362. (b) Liao, Y. H.; Moss, J. R. Organometallics 1995, 14, 2130. (c) Huck, W. T. S.; van Veggel, F. C. J. M.; Kropman, B. L.; Blank, D. H. A.; Keim, E. G.; Smithers, M. M. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 8293. (d) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D.; van Koten, G. Nature 1994, 372, 659. (e) Fillaut, J.-L.; Linares, J.; Astruc, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2460. (f) Achar, S.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1994, 1895.
17. For organometallic dendrimers see for example: (a) Seyferth, D.; Kugita, T.; Rheingold, A.; Yap, G. P. A. Organometallics 1995, 14, 5362. (b) Liao, Y. H.; Moss, J. R. Organometallics 1995, 14, 2130. (c) Huck, W. T. S.; van Veggel, F. C. J. M.; Kropman, B. L.; Blank, D. H. A.; Keim, E. G.; Smithers, M. M. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 8293. (d) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D.; van Koten, G. Nature 1994, 372, 659. (e) Fillaut, J.-L.; Linares, J.; Astruc, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2460. (f) Achar, S.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1994, 1895.
18. Alonso, B.; Cuadrado, I.; Morán, M.; Losada, J. J. Chem. Soc., Chem. Commun. 1994, 2575.
19. Lobete, F.; Cuadrado, I.; Casado, C. M.; Alonso, B.; Morán, M.; Losada, J. J. Organomet. Chem. 1996, 509, 109.
20. Cuadrado, I.; Morán, M.; Moya, A.; Casado, C. M.; Barranco, M.; Alonso, B. Inorg. Chim. Acta, in press.
21. Alonso, B.; Moran, M.; Casado, C. M.; Lobete, F.; Losada, J.; Cuadrado, I. Chem. Mater. 1995, 7, 1440.
22. Casado, C. M.; Morán, M.; Losada, J.; Cuadrado, I. Inorg. Chem. 1995, 34, 1668.
23. Part of these results were first presented at the 211th National Meeting of the American Chemical Society, New Orleans, LA, March 24-28, 1996, and at the NATO Advanced Research Workshop on Physical Supramolecular Chemistry, Miami, FL, Jan 7-10, 1996.
24. 5)) are the terminal groups.
25. Pauson, P. L.; Watts, W. E. J. Chem. Soc. 1963, 2990.
26. 2/hexane.
27. The same phenomenon has been also observed in large poly(propylenimine) dendrimers functionalized at the periphery with organic groups. See: (a) Jansen, J. F. G. A.; de Brabander-van den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226. (b) Moszner, N.; Völkel, T., Rheinberger, V. Macromol. Chem. Phys. 1996, 621.
28. The same phenomenon has been also observed in large poly(propylenimine) dendrimers functionalized at the periphery with organic groups. See: (a) Jansen, J. F. G. A.; de Brabander-van den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226. (b) Moszner, N.; Völkel, T., Rheinberger, V. Macromol. Chem. Phys. 1996, 621.
29. -1. Microanalytical data for the fourth and fifth generations are not included because of the n-hexane inclusion. Optimization of the GPC analyses conditions is currently under investigation at DSM research laboratories and will be detailed in the full paper.
30. NMR spectroscopy has been used as a valuable technique for detecting and assigning structural defects in poly(propylenimine)-based dendrimers even at the stage of the higher generations and for the characterization of large organometallic dendrimers. See: (a) de Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1308. (b) Wörner, C.; Mülhaupt, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1306. See also refs 2d, 4b, and 14a.
31. NMR spectroscopy has been used as a valuable technique for detecting and assigning structural defects in poly(propylenimine)-based dendrimers even at the stage of the higher generations and for the characterization of large organometallic dendrimers. See: (a) de Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1308. (b) Wörner, C.; Mülhaupt, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1306. See also refs 2d, 4b, and 14a.
32. The matrix for FAB-MS was 3-nitrobenzyl alcohol, and for MALDI-TOF-MS determinations silver trifluoroacetate was used as a cationization compound. The characterization of the fourth- and fifthgeneration ferrocenyl dendrimers by MALDI-TOF mass spectrometric analysis will be published elsewhere.
33. 1/2 = +0.59, +0.57, +0.59, +0.58, and +0.59 V, for x = 4, 8, 16, 32, and 64 respectively. For details of the electrochemical equipment, see ref 9.
34. The NPV technique has been used in order to minimize precipitation of the oxidized dendrimers. See: (a) Flanagan, J. B.; Margel, S.; Bard, A. J.; Anson, F. C. J. Am. Chem. Soc. 1978, 100, 4248. (b) Albagly, D.; Bazan, G.; Wrighton, M. S.; Schrock, R. R. J. Am. Chem. Soc. 1992, 114, 4150.
35. The NPV technique has been used in order to minimize precipitation of the oxidized dendrimers. See: (a) Flanagan, J. B.; Margel, S.; Bard, A. J.; Anson, F. C. J. Am. Chem. Soc. 1978, 100, 4248. (b) Albagly, D.; Bazan, G.; Wrighton, M. S.; Schrock, R. R. J. Am. Chem. Soc. 1992, 114, 4150.