Organometallic macrocycles and cyclic polymers by the bipyridine-initiated photolytic ring opening of a silicon-bridged [1]ferrocenophane

Angewandte Chemie - International Edition

Volumn 46, Issue 47, 2007, Pages 9069-9072

  Chan, Wing Yan ^b   Lough, Alan J ^b   Manners, Ian ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Bipyridine; Cyclic polymers; Ferrocenophanes; Metallacycles; Ring opening polymerization

Indexed keywords

OLIGOMERS; PHOTOLYSIS; POLYMERS; PYRIDINE; RING OPENING POLYMERIZATION; SILICON;

CYCLIC POLYMERS; FERROCENOPHANES; METALLACYCLES;

ORGANOMETALLICS;

EID: 36849016549     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703430     Document Type: Article

References (39)

1. Cyclic Polymers, 2nd ed. (Ed.: J. A. Semlyen), Kluwer Academic Publishers, Dordrecht, 2000.
2. C. W. Bielawski, D. Benitez, R. H. Grubbs, Science 2002, 297, 2041-2044.
3. M. Tamm, A. Kunst, E. Herdtweck, Chem. Commun. 2005, 1729-1731.
4. 3·THF. See: K. Temple, A. J. Lough, J. B. Sheridan, I. Manners, J. Chem. Soc. Dalton Trans. 1998, 2799-2806.
5. a) D. A. Foucher, B.-Z. Tang, I. Manners, J. Am. Chem. Soc. 1992, 114, 6246-6248;
6. b) D. E. Herbert, U. F. J. Mayer, I. Manners, Angew. Chem. 2007, 119, 5152-5173;
7. Angew. Chem. Int. Ed. 2007, 46, 5060-5081;
8. c) V. Bellas, M. Rehahn, Angew. Chem. 2007, 119, 5174-5197;
9. Angew. Chem. Int. Ed. 2007, 46, 5082-5104.
10. In this notation, the superscript refers to the degree of polymerization.
11. a) D. L. Zechel, D. A. Foucher, J. K. Pudelski, G. P. A. Yap, A. L. Rheingold, I. Manners, J. Chem. Soc. Dalton Trans. 1995, 1893-1899;
12. b) Y. Ni, R. Rulkens, J. K. Pudelski, I. Manners, Macromol. Rapid Commun. 1995, 16, 637-641;
13. c) J. Park, Y. Seo, S. Cho, D. Whang, K. Kim, T. Chang, J. Organomet. Chem. 1995, 489, 23-25;
14. d) G. Calleja, F. Carré, G. Cerveau, P. Labbé, L. Coche-Guérente, Organometallics 2001, 20, 4211-4215;
15. e) A. Berenbaum, A. J. Lough, I. Manners, Organometallics 2002, 21, 4415-4424.
16. For selected recent examples of [1.1]ferrocenophanes containg other bridging atoms, see: H. Brunner, J. Klankermayer, M. Zabel, J. Organomet. Chem. 2000, 601, 211-219;
17. W. Uhl, I. Hahn, A. Jantschak, T. Spies, J. Organomet. Chem. 2001, 637-639, 300-303;
18. A. Althoff, P. Jutzi, N. Lenze, B. Neumann, A. Stammler, H.-G. Stammler, Organometallics 2002, 21, 3018-3022;
19. M. Scheibitz, R. F. Winter, M. Bolte, H.-W. Lerner, M. Wagner, Angew. Chem. 2003, 115, 954-957;
20. Angew. Chem. Int. Ed. 2003, 42, 924-927;
21. H. Braunschweig, C. Burschka, G. K. B. Clentsmith, T. Kupfer, K. Radacki, Inorg. Chem. 2005, 44, 4906-4908;
22. J. A. Schachner, G. A. Orlowski, J. W. Quail, H.-B. Kraatz, J. Müller, Inorg. Chem. 2006, 45, 454-459.
23. 4]metallocenophanes containing ferrocene, ruthenocene, or cobaltocenium units have been reported in low yields. See: U. T. Mueller-Westerhoff, Angew. Chem. 1986, 98, 700-716;
24. Angew. Chem. Int. Ed. Engl. 1986, 25, 702-717, and references therein.
25. n]ferrocenophane, it was the largest known cyclic ferrocene oligomer at the time. See: B. Grossmann, J. Heinze, E. Herdtweck, F. H. Köhler, H. Nöth, H. Schwenk, M. Spiegler, W. Wachter, B. Weber, Angew. Chem. 1997, 109, 384-386;
26. Angew. Chem. Int. Ed. Engl. 1997, 36, 387-389.
27. M. Tanabe, S. C. Bourke, D. E. Herbert, A. J. Lough, I. Manners, Angew. Chem. 2005, 117, 6036-6040;
28. Angew. Chem. Int. Ed. 2005, 44, 5886-5890.
29. For work on Fe-Cp bond-cleavage reactions in phosphorus-bridged [1]ferrocenophanes, see: T. Mizuta, Y. Imamura, K. Miyoshi, J. Am. Chem. Soc. 2003, 125, 2068-2069.
30. a) M. Tanabe, I. Manners, J. Am. Chem. Soc. 2004, 126, 11434-11435;
31. b) M. Tanabe, G. W. M. Vandermeulen, W. Y. Chan, P. W. Cyr, L. Vanderark, D. A. Rider, I. Manners, Nat. Mater. 2006, 5, 467-470.
32. We have recently explored the analogous chemistry with terpyridine ligands, and the results are very different, see: W. Y. Chan, A. J. Lough, I. Manners, Chem. Eur. J. 2007, DOI: 10.1002/chem.200700420.
33. 2 refers to the cyclic dimer disila[1.1]ferrocenophane.
34. See the Supporting Information for full experimental details.
35. 6 9%.
36. R. Rulkens, A. J. Lough, I. Manners, S. R. Lovelace, C. Grant, W. E. Geiger, J. Am. Chem. Soc. 1996, 118, 12683-12695.
37. A. J. Lough, I. Manners, R. Rulkens, Acta Crystallogr. Sect. C 1994, 50, 1667-1669.
38. K. H. Pannell, V. V. Dementiev, H. Li, F. Cervantes-Lee, M. T. Nguyen, A. F. Diaz, Organometallics 1994, 13, 3644-3650.
39. It is known that the most probable molecular weights obtained by MALDI-TOF MS and GPC only show good agreement for polymers with a narrow molecular weight distribution (PDI < 1.1). For more polydisperse polymers, the most probable molecular weight obtained by MALDI-TOF MS is significantly lower than that obtained from GPC measurements. For details, see M. W. F. Nielen, Mass Spectrom. Rev. 1999, 18, 309-344, and references therein.