Synthesis, X-ray structure, and ring-opening polymerization of pentacoordinate silicon-bridged [1]ferrocenophane

Organometallics

Volumn 24, Issue 6, 2005, Pages 1053-1055

  Hatanaka, Yasuo ^a   Okada, Shingo ^b   Minami, Tatsuya ^a   Goto, Midori ^b   Shimada, Kayori ^b  

^a Osaka Prefecture University   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CATALYSTS; CRYSTALLIZATION; ELECTRON ENERGY LEVELS; ORGANIC POLYMERS; PHYSICAL PROPERTIES; PRECIPITATION (CHEMICAL); RING OPENING POLYMERIZATION; SILICON; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CATIONIC RING-OPENING POLYMERIZATION; EXCITATION ENERGY; FERROCENOPHANES; SILICON-CONTAINING POLYMERS;

ORGANOMETALLICS;

EID: 15944403172     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om040132r     Document Type: Article

References (28)

1. For reviews, see: (a) Manners, I. Can. J. Chem. 1998, 76, 371. (b) Kulbaba, K.; Manners, I. Macromol. Rapid Commun. 2001, 22, 711.
2. For reviews, see: (a) Manners, I. Can. J. Chem. 1998, 76, 371. (b) Kulbaba, K.; Manners, I. Macromol. Rapid Commun. 2001, 22, 711.
3. (a) Tandura, a N.; Voronkov, M. G.; Alkseev, N. V. Top. Curr. Chem. 1986, 131, 99.
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7. (b) Muguruma, C.; Koga, N.; Hatanaka, Y.; El-Sayed, I.; Mikami, M.; Tanaka, M. J. Phys. Chem. A 2000, 104, 4928.
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9. Manners and co-workers have reported the synthesis of penta-coordinate silicon-bridged [1]ferrocenophane having pseudo-trigonal-bipyramidal geometry at the silicon atom: (a) Jäkle, F.; Vejzovic, E.; Nicole Power-Billard, K.; MacLachlan, M. J.; Lough, A. J.; Manners, I. Orgonometallics 2000, 19, 2826. Thermal ring-opening polymerization of this compound under reflux conditions in xylene gave poly(ferrocenylsilane) with tetracoordinate silicon atoms in the polymer backbone: (b) Jäkle, F.; Wang, Z.; Manners, I. Macromol. Rapid Commun. 2000, 21, 1291.
10. Manners and co-workers have reported the synthesis of penta-coordinate silicon-bridged [1]ferrocenophane having pseudo-trigonal-bipyramidal geometry at the silicon atom: (a) Jäkle, F.; Vejzovic, E.; Nicole Power-Billard, K.; MacLachlan, M. J.; Lough, A. J.; Manners, I. Orgonometallics 2000, 19, 2826. Thermal ring-opening polymerization of this compound under reflux conditions in xylene gave poly(ferrocenylsilane) with tetracoordinate silicon atoms in the polymer backbone: (b) Jäkle, F.; Wang, Z.; Manners, I. Macromol. Rapid Commun. 2000, 21, 1291.
11. -1, 1454 observed reflections (I > 3σ(I)), R1 = 0.023, wR2 = 0.0326, Rigaku AFC7R diffractometer. Mo Kα radiation (λ = 0.710 69 A), graphite monochromator. The file CCDC 255494 contains the supplementary crystallographic data for compound 4. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/cgi-bin/ catreq.cgi (or from the Cambridge Crystallographic Centre, 12 Union Road, Cambridge CB21EZ, U.K.; fax (+44)1223-336-033; e-mail deposit@ccdc.cam.ac.uk).
12. -1, 964 observed reflections (I > 2σ(I)), R1 = 0.040, wR2 = 0.1509, Rigaku AFC7R diffractometer, Mo Kα radiation (λ = 0.710 69 Å), graphite monochromator. The file CCDC 255493 contains the supplementary crystallographic data for compound 1. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/cgi-hin/ catreq.cgi (or from the Cambridge Crystallographic Centre, 12 Union Road, Cambridge CB21EZ, U.K.; fax (+44)1223-336-033; e-mail deposit@ccdc.cam.ac.uk).
13. For related X-ray structures of pentacoordinate silicon compounds see: (a) Hillyard, R. W., Jr.; Ryan, C. M.; Yoder, C. H. J. Organomet. Chem. 1978, 153, 369. (b) Yoder, C. H.; Ryan, C. M.; Martin, G. F.; Ho, P. S. J. Organomet. Chem. 1980, 190, 1 and references therein, (c) El-Sayed, I.; Hatanaka, Y.; Onozawa, S.; Tanaka, M. J. Am. Chem. Soc. 2001, 123, 3597. (d) Pestunovich, V. A.; Valery, F. S.; Voronkov, M. G. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Basel, Switzerland, 1995; pp 69-82.
14. For related X-ray structures of pentacoordinate silicon compounds see: (a) Hillyard, R. W., Jr.; Ryan, C. M.; Yoder, C. H. J. Organomet. Chem. 1978, 153, 369. (b) Yoder, C. H.; Ryan, C. M.; Martin, G. F.; Ho, P. S. J. Organomet. Chem. 1980, 190, 1 and references therein, (c) El-Sayed, I.; Hatanaka, Y.; Onozawa, S.; Tanaka, M. J. Am. Chem. Soc. 2001, 123, 3597. (d) Pestunovich, V. A.; Valery, F. S.; Voronkov, M. G. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Basel, Switzerland, 1995; pp 69-82.
15. For related X-ray structures of pentacoordinate silicon compounds see: (a) Hillyard, R. W., Jr.; Ryan, C. M.; Yoder, C. H. J. Organomet. Chem. 1978, 153, 369. (b) Yoder, C. H.; Ryan, C. M.; Martin, G. F.; Ho, P. S. J. Organomet. Chem. 1980, 190, 1 and references therein, (c) El-Sayed, I.; Hatanaka, Y.; Onozawa, S.; Tanaka, M. J. Am. Chem. Soc. 2001, 123, 3597. (d) Pestunovich, V. A.; Valery, F. S.; Voronkov, M. G. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Basel, Switzerland, 1995; pp 69-82.
16. For related X-ray structures of pentacoordinate silicon compounds see: (a) Hillyard, R. W., Jr.; Ryan, C. M.; Yoder, C. H. J. Organomet. Chem. 1978, 153, 369. (b) Yoder, C. H.; Ryan, C. M.; Martin, G. F.; Ho, P. S. J. Organomet. Chem. 1980, 190, 1 and references therein, (c) El-Sayed, I.; Hatanaka, Y.; Onozawa, S.; Tanaka, M. J. Am. Chem. Soc. 2001, 123, 3597. (d) Pestunovich, V. A.; Valery, F. S.; Voronkov, M. G. In Progress in Organosilicon Chemistry; Marciniec, B., Chojnowski, J., Eds.; Gordon and Breach: Basel, Switzerland, 1995; pp 69-82.
17. For X-ray structures of sila[1]ferrocenophanes see: (a) Stoeckli-Evans, H.; Osborne, A. G.; Whiteley, R. H. Helv. Chim. Acta 1976, 59, 2402. (b) Butler, I. R.; Cullen, W. R.; Retting, S. J. Can. J. Chem. 1987, 65, 1452. (c) Finckh, W.; Tang. B.-Z.; Foucher, D. A.; Zamble, D. B.; Ziembinski, R.; Lough, A.; Manners, I. Organometallics 1993, 12, 823. See also ref 4a.
18. For X-ray structures of sila[1]ferrocenophanes see: (a) Stoeckli-Evans, H.; Osborne, A. G.; Whiteley, R. H. Helv. Chim. Acta 1976, 59, 2402. (b) Butler, I. R.; Cullen, W. R.; Retting, S. J. Can. J. Chem. 1987, 65, 1452. (c) Finckh, W.; Tang. B.-Z.; Foucher, D. A.; Zamble, D. B.; Ziembinski, R.; Lough, A.; Manners, I. Organometallics 1993, 12, 823. See also ref 4a.
19. For X-ray structures of sila[1]ferrocenophanes see: (a) Stoeckli-Evans, H.; Osborne, A. G.; Whiteley, R. H. Helv. Chim. Acta 1976, 59, 2402. (b) Butler, I. R.; Cullen, W. R.; Retting, S. J. Can. J. Chem. 1987, 65, 1452. (c) Finckh, W.; Tang. B.-Z.; Foucher, D. A.; Zamble, D. B.; Ziembinski, R.; Lough, A.; Manners, I. Organometallics 1993, 12, 823. See also ref 4a.
20. e value, see: Tamao, K.; Hayashi, T.; Ito, Y.; Shiro, M. Organometallics 1992, 11, 2099.
21. 6) δ -0.27.
22. 29Si chemical shifts for pentacoordinate silicon usually exhibit an upfield shift relative to tetracoordinate silicon: Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, England, 1998; Vol. 2, pp 1339-1445.
23. Hatanaka, Y.; Reddy, A. C. S.; Tanaka, M.; Onozawa, S. Jpn. Kokai Tokkyo Koho JP2002265477 2002; Chem. Abstr. 2003, 137, 248114.
24. Hatanaka, Y.; Reddy, A. C. S.; Tanaka, M.; Onozawa, S. Jpn. Kokai Tokkyo Koho JP2002265477 2002; Chem. Abstr. 2003, 137, 248114.
25. Baumgartner, T.; Jäkle, F.; Rulkens, R.; Zech, G.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2002, 124, 10062-10070.
26. 2) δ -57.31, -59.78.
27. Sohn, Y. S.; Hendrickson, D. N.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3603.
28. Foucher, D. A.; Ziembinski, R.; Tang, B.-Z.; Macdonald, P. M.; Masson, J.; Jaeger, R.; Vancso, J.; Manners, I. Macromolecules 1993, 26, 2878.