Skip to main content
Log in

Ferrocenyl-terminated Dendrimers: Design for Applications in Molecular Electronics, Molecular Recognition and Catalysis

  • Review Paper
  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

This micro-review shows how a simple but powerful organometallic C–H activation could be made very useful for the construction of a large variety of stars, dendritic cores, dendrons and dendrimers of variable sizes including giant dendrimers and gold-nanoparticle-cored dendrimers. The synthesis of ferrocenyl-terminated dendrimers was then achieved by reactions of chlorocarbonylferrocene with polyamino dendrimers, ferrocenylsilylation of polyolefin dendrons and dendrimers and “click” reactions of ferrocenyl acetylene with azido-terminated dendrimers. The functions of these metallodendrimers include molecular electronics (molecular batteries), molecular redox recognition and sensing and catalysis using dendritic stabilization of nanoparticle catalysts.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15

Similar content being viewed by others

References

  1. I. Manners, Chem. Commun. 857 (1999); P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 99, 1515 (1999); C.M. Casado, I. Cuadrado, M. Morán, B. Alonso, J.B. Garcia, B. Gonzales, J. Losada, Coord. Chem. Rev. 185–186, 53 (1999); D. Astruc, in Frontiers in Transition Metal-Containing Polymers, ed. by A.S. Abd-El-Aziz, I. Manners (Wiley-Interscience, John Wiley and Sons, Inc., New York, 2007)

  2. G.R. Newkome, C.N. Moorefield, F. Vögtle, Dendrimers and Dendrons. Concept, Syntheses, Applications (Wiley-VCH, Weinheim, 2001); in Dendrimers and Other Dendritic Polymers, ed. by D. Tomalia, J.M.J. Fréchet (Wiley-VCH, New York, 2002); in Dendrimers and Nanosciences, ed. by D. Astruc (Elsevier, Amsterdam, 2003), C. R. Chimie, 6, 1117 (2003)

  3. J.F.G.A. Jansen, E.M.M. de Brabander-van den Berg, E.W. Meijer, Science 266, 1226 (1994); A.W. Bosman, E.W. Jansen, E.W. Meijers, Chem. Rev. 99, 1665 (1999); G.R. Newkome, E. He, C.N. Moorefield, Chem. Rev. 99, 1689 (1999)

  4. S.C. Zimmerman, F.W. Zeng, D.E.C. Reichert, S.V. Kolotuchin, Science 271, 1095 (1996); F.W. Zeng, S.C. Zimmerman, Chem. Rev. 97, 1681 (1997)

  5. D. Astruc, J.-R. Hamon, G. Althoff, E. Román, P. Batail, P. Michaud, J.-P. Mariot, F. Varret, D. Cozak, J. Am. Chem. Soc. 101, 5445 (1979); J.-R. Hamon, D. Astruc, P. Michaud, J. Am. Chem. Soc. 103, 758 (1981); D. Astruc, Acc. Chem. Res. 19, 377 (1986)

    Google Scholar 

  6. J.C. Green, M.R. Kelly, M.P. Payne, E.A. Seddon, D. Astruc, J.-R. Hamon, P. Michaud, Organometallics 2, 211 (1983)

    Article  CAS  Google Scholar 

  7. D. Astruc, E. Román, J.-R. Hamon, P. Batail, J. Am. Chem. Soc. 101, 2240 (1979); J.-R. Hamon, D. Astruc, E. Román, P. Batail, J.J. Mayerle, J. Am. Chem. Soc. 103, 2431 (1981); D. Astruc, J.-R. Hamon, E. Román, P. Michaud, J. Am. Chem. Soc. 103, 7502 (1981); H. Trujillo, C. Casado, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 121, 5674 (1999); D. Astruc, Acc. Chem. Res. 33, 287 (2000); D. Astruc, Bull. Chem. Soc. Jpn. 80, 1672 (2007)

  8. J.-R. Hamon, J.-Y. Saillard, A. Le Beuze, M. McGlinchey, D. Astruc, J. Am. Chem. Soc. 104, 7549 (1982)

    Article  CAS  Google Scholar 

  9. E. Buhlein, W. Wehner, F. Vögtle, Synthesis 155 (1978)

  10. F. Moulines, D. Astruc, Angew. Chem. Int. Ed. Engl. 27, 1347 (1988); F. Moulines, D. Astruc, J. Chem. Soc. Chem. Commun. 614 (1989); F. Moulines, B. Gloaguen, D. Astruc, Angew. Chem. Int. Ed. Engl. 28, 458 (1992); F. Moulines, L. Djakovitch, R. Boese, B. Gloaguen, W. Thiel, J.-L. Fillaut, M.-H. Delville, D. Astruc, Angew. Chem. Int. Ed. Engl. 105, 1132 (1993); J.-L. Fillaut, J. Linares, D. Astruc, Angew. Chem. Int. Ed. Engl. 33, 2460 (1994); H.W. Marx, F. Moulines, T. Wagner, D. Astruc, Angew. Chem. Int. Engl. 35, 1701 (1996)

  11. D. Astruc, Tetrahedron. 39, 4027 (1983) (Tetrahedron Report N° 157); A. Abd-El-Aziz, Coord. Chem. Rev. 203, 219 (2000)

  12. D. Catheline, D. Astruc, J. Organometal. Chem. 248, C9 (1983); M. Lacoste, H. Rabaa, D. Astruc, A. Le Beuze, J.-Y. Saillard, G. Précigoux, C. Courseille, N. Ardoin, W. Bowyer, Organometallics. 8, 2233 (1989); J. Ruiz Aranzaes, Inorg. Chim. Acta. (2007) ASAP; Bull. Soc. Chim. J. (2007), ASAP

  13. V. Sartor, L. Djakovitch, J.-L. Fillaut, F. Moulines, F. Neveu, V. Marvaud, J. Guittard, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 121, 2929 (1999)

    Article  CAS  Google Scholar 

  14. V. Sartor, S. Nlate, J.-L. Fillaut, F. Djakovitch, F. Moulines, V. Marvaud, F. Neveu, J.-C. Blais, New J. Chem. 24, 351 (2000); J. Ruiz Aranzaes, L. Djakovitch, D. Astruc, Arkivoc, AL 1794-FP (2006)

  15. J. Ruiz, G. Lafuente, S. Marcen, C. Ornelas, S. Lazare, E. Cloutet, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 125, 7250 (2003)

    Article  CAS  Google Scholar 

  16. G.R. Newkome, Z. Yao, G.R. Baker, V.K. Gupta, J. Org. Chem. 50, 2003 (1985); G.R. Newkome, Pure Appl. Chem. 70, 2337 (1998); V.V. Narayanan, G.R. Newkome, Top. Curr. Chem. 197, 19 (1998)

    Google Scholar 

  17. S.W. Krsda, D. Seyferth, J. Am. Chem. Soc. 120, 3604 (1998)

    Article  Google Scholar 

  18. C. Ornelas, J. Ruiz, D. Astruc, Org. Lett. 8, 2751 (2006)

    Article  CAS  Google Scholar 

  19. A.W. van der Made, P.W.N.M. van Leeuwen, R.A.C. Brandes, Adv. Mater. 5, 466 (1993)

    Article  Google Scholar 

  20. D. Astruc, C. Valério, J.-L. Fillaut, J. Ruiz, J.-R. Hamon, F. Varret, in Supramolecular Magnetism, ed. by O. Kahn (NATO ASAI Series, Kluwer, Dordrecht), p. 107 (1996); C. Valério, J.-L Fillaut, J. Ruiz, J. Guittard; J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 119, 2588 (1997); J. Ruiz, M.-J. Ruiz-Medel, M.-C. Daniel, J.-C. Blais, D. Astruc, Chem. Commun. 464 (2003); M.-C. Daniel, J. Ruiz, J.-C. Blais, N. Daro, D. Astruc, Chemistry, Eur. J. 9, 4371 (2003); M.-C. Daniel, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 125, 1150 (2003); M.-C. Daniel, F. Ba, J. Ruiz, D. Astruc, Inorg. Chem. 43, 8649 (2004)

  21. S. Nlate, J. Ruiz, J.-C. Blais, D. Astruc, Chem. Commun. 417 (2000); S. Nlate, J. Ruiz, V. Sartor, R. Navarro, J.-C. Blais, D. Astruc, Chem. Eur. J. 6, 2544 (2000)

  22. M.-C. Daniel, J. Ruiz, S. Nlate, J. Palumbo, J.-C. Blais, D. Astruc, Chem. Commun. 2001 (2000); M.-C. Daniel, J. Ruiz, S. Nlate, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 125, 2617 (2003); M-C. Daniel, D. Astruc, Chem. Rev. 104, 293 (2004); D. Astruc, M.-C. Daniel, J. Ruiz, Chem. Commun (feature article) 2637 (2004)

  23. H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem., Int. Ed. 40, 2004 (2001); V.D. Bock, H. Hiemstra, J.H. van Maarseveen, Eur. J. Org. Chem. 51 (2006)

  24. C. Ornelas, J.R. Aranzaes, E. Cloutet, S. Alves, D. Astruc, Angew. Chem., Int. Ed. Engl. 46, 872 (2007)

    Article  CAS  Google Scholar 

  25. C. Ornelas, L. Salmon, J. Ruiz Aranzaes, D. Astruc, Chem. Commun. (2007) ASAP; C. Ornelas, L. Salmon, J. Ruiz Aranzaes, D. Astruc, Chem. Eur. J. (in press)

  26. H. Bönnemann, W. Brijoux, in Active Metal, ed. by A. Fürstner (VCH, Weinheim, 1996), p. 339; M. T. Reetz, W. Helbig, S. A. Quaiser, in Active Metals, ed. by A. Fürstner (VCH, Weinheim, 1996), p. 279; B.F.G. Johnson, Coord. Chem. Rev. 190, 1269 (1999); A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 102, 3757 (2002); S. Mandal, P.R. Selvakannan, D. Roy, R.V. Chaudhari, M. Sastry, Chem. Commun. 3002 (2002); J. Dupont, G.S. Fonseca, A.P. Umpierre, P.F.P. Fichner, J. Am. Chem. Soc. 124, 4228 (2002); H. Ohde, C.M. Wai, J. Kim, M. Ohde, J. Am. Chem. Soc. 124, 4540 (2002); A. Roucoux, J. Schulz, H. Patin, Adv. Syn. Catal. 345, 222 (2003); H. Bönnemann, K.S. Nagabushana in Encyclopedia of Nanoscience and Nanotechnology, ed. by H. S. Nalwa (ASP, Stevenson Ranch, Ca 2004, 1), p. 777; M. Bronstein, in Encyclopedia of Nanoscience and Nanotechnology, vol. 7, ed. by H. S. Nalwa (ASP, Stevenson Ranch, 2004), p. 193; M. Bronstein, in Dekker Encyclopedia of Nanoscience and Nanotechnology, ed. by J.A. Schwarz, C. I. Contescu, K. Putyera (Marcel Dekker, New York, 2004), p. 2903

    Google Scholar 

  27. N. Toshima, Y. Yonezawa, New J. Chem. 22, 1179 (1998)

    Article  CAS  Google Scholar 

  28. D. Astruc, F. Lu, J. Ruiz Aranzaes, Angew. Chem. Int. Ed. 44, 7852 (2005); D. Astruc, Inorg. Chem. 46, 1884 (2007)

    Google Scholar 

  29. M. Zhao, L. Sun, R.M. Crooks, J. Am. Chem. Soc. 120, 4877 (1998); L. Balogh, D.A. Tomalia, J. Am. Chem. Soc. 120, 7355 (1998)

  30. K. Esumi, A. Suzuki, N. Aihara, K. Usui, K. Torigoe, Langmuir. 14, 3157 (1998)

    Article  CAS  Google Scholar 

  31. R.M. Crooks, M. Zhao, L. Sun, V. Chechik, L.K. Yeung, Acc. Chem. Res. 34, 181 (2001); R.W.J. Scott, O.M. Wilson, R.M.J. Crooks, Phys. Chem. B. 109, 692 (2005); B.D. Chandler, J.D. Gilbertson, Top. Organomet. Chem. 20, 97 (2006)

  32. A. Diallo, C. Ornelas, J. Ruiz Aranzaes, L. Salmon, D. Astruc, Angew. Chem., Int. Ed. Engl. 47 (2007), ASAP

  33. A.H.M. de Vries, F.J. Parlevliet, L. Schmeder-van de Vondervoort, J.H.M. Mommers, H.J.W. Henderickx, M.A.N. Walet, A.H.M. de Vries, Adv. Synth. Catal. 344, 996 (2002); A.H.M. de Vries, J.M.C.A. Mulders, J.H.M. Mommers, H.J.W. Hendericks, J.G., de Vries, Org. Lett. 5, 3285 (2003); J.G. de Vries, Dalton Trans. 421 (2006)

Download references

Acknowledgement

The valuable efforts and contributions of students and colleagues cited in the references to the subject of this micro-review and financial assistance from the Institut Universitaire de France (IUF), the Université Bordeaux I, the Centre National de la Recherche Scientifique (CNRS) and the Agence Nationale de la Recherche (ANR) are gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Didier Astruc.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Astruc, D., Ornelas, C. & Ruiz Aranzaes, J. Ferrocenyl-terminated Dendrimers: Design for Applications in Molecular Electronics, Molecular Recognition and Catalysis. J Inorg Organomet Polym 18, 4–17 (2008). https://doi.org/10.1007/s10904-007-9191-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-007-9191-7

Keywords

Navigation