Photoinduced face-inversion of conjugated tetraene ligands on a Pd-Pd-Pd moiety

Journal of the American Chemical Society

Volumn 124, Issue 48, 2002, Pages 14288-14289

  Murahashi, Tetsuro ^a   Higuchi, Yutaka ^a   Katoh, Tetsuya ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; LIGAND; PALLADIUM;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; CRYSTALLIZATION; DISSOCIATION; ISOMERISM; MOLECULAR INTERACTION; PHOTOCHEMISTRY; STEREOSPECIFICITY; THERMOSTABILITY; X RAY CRYSTALLOGRAPHY;

EID: 0037021531     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0208254     Document Type: Article

References (32)

1. (a) Murahashi, T.; Mochizuki, E.; Kai, Y.; Kurosawa, H. J. Am. Chem. Soc. 1999. 121, 10660.
2. (b) Murahashi, T.; Nagai, T.; Mino, Y.; Mochizuki, E.; Kai, Y.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 6927.
3. (a) Saltiel, J.; Sun, Y.-P. In Photochromism, Molecules, and Systems; Durr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; p 64,
4. (b) Allen, M. T.; Whitten, D. G. Chem. Rev. 1989, 89, 1691.
5. (c) Kohler, B. E. Chem. Rev. 1993, 93, 41.
6. (a) Geoffroy, G. L.; Wrighton, M. S. Organometallic Photochemistry; Academic Press: New York, 1979. For selected recent literature:
7. (b) Yang, H.; Snee, P. T.; Kotz, K. T.; Payne, C. K.; Harris, C. B. J. Am. Chem. Soc. 2001, 123, 4204 and references therein.
8. (c) Reinking, M. K.: Kullberg, M. L.; Culter, A. R.; Kubiak, C. P. J. Am. Chem. Soc. 1985, 107, 3517.
9. (d) Cotton, F. A.; Haefner, S. C.; Sattelberger, A. P. J. Am. Chem. Soc. 1996, 118, 5486 and references therein.
10. For some photoresponses of organometallic complexes containing metalmetal bonds: (a) Boese, R.; Cammack, J. K.; Matzger, A. J.; Pflug, K.; Tolman, W. B.; Vollhardt, K. P. C.; Weidman, T. W. J. Am. Chem. Soc. 1997, 119, 6757. (b) Matsubara, K.; Oda, T.; Nagashima. H. Organometallics 2001, 20, 881. (c) Casey, C. P.: Cariño, R. S.; Hayashi, R. K.; Schladetzky, K. D. J. Am. Chem. Soc. 1996, 118, 1617. (d) Burger, P. Angew. Chem., Int. Ed. 2001, 40, 1917.
11. For some photoresponses of organometallic complexes containing metalmetal bonds: (a) Boese, R.; Cammack, J. K.; Matzger, A. J.; Pflug, K.; Tolman, W. B.; Vollhardt, K. P. C.; Weidman, T. W. J. Am. Chem. Soc. 1997, 119, 6757. (b) Matsubara, K.; Oda, T.; Nagashima. H. Organometallics 2001, 20, 881. (c) Casey, C. P.: Cariño, R. S.; Hayashi, R. K.; Schladetzky, K. D. J. Am. Chem. Soc. 1996, 118, 1617. (d) Burger, P. Angew. Chem., Int. Ed. 2001, 40, 1917.
12. For some photoresponses of organometallic complexes containing metalmetal bonds: (a) Boese, R.; Cammack, J. K.; Matzger, A. J.; Pflug, K.; Tolman, W. B.; Vollhardt, K. P. C.; Weidman, T. W. J. Am. Chem. Soc. 1997, 119, 6757. (b) Matsubara, K.; Oda, T.; Nagashima. H. Organometallics 2001, 20, 881. (c) Casey, C. P.: Cariño, R. S.; Hayashi, R. K.; Schladetzky, K. D. J. Am. Chem. Soc. 1996, 118, 1617. (d) Burger, P. Angew. Chem., Int. Ed. 2001, 40, 1917.
13. For some photoresponses of organometallic complexes containing metalmetal bonds: (a) Boese, R.; Cammack, J. K.; Matzger, A. J.; Pflug, K.; Tolman, W. B.; Vollhardt, K. P. C.; Weidman, T. W. J. Am. Chem. Soc. 1997, 119, 6757. (b) Matsubara, K.; Oda, T.; Nagashima. H. Organometallics 2001, 20, 881. (c) Casey, C. P.: Cariño, R. S.; Hayashi, R. K.; Schladetzky, K. D. J. Am. Chem. Soc. 1996, 118, 1617. (d) Burger, P. Angew. Chem., Int. Ed. 2001, 40, 1917.
14. The thermal face-inversion of simple π-olefin ligands at a mononuclear metal center has been well-investigated: Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174. In this paper, a nondissociative intramolecular face-inversion of π-olefin ligands was revealed.
15. Murahashi, T.; Nagai, T.; Okuno, T.; Matsutani, T.; Kurosawa, H. Chem. Commun. 2000, 1689.
16. Rac and meso refer to the relative stacking mode (staggered and eclipsed) of two polyene frameworks.
17. -1, 694 variables refined with 7971 reflections collected at 223 K with I > 3σ to R = 0.031.
18. 4Ph.
19. In this case, however, formation of a slight amount of unidentified product was also observed (8%, δ 1.10 and 1.03 for t-Bu region).
20. 1H NMR signals of 3-rac and 3-meso were assigned by comparison with those of 1 or 2, respectively (see Supporting Information).
21. The average value of intramolecular {(phenyl carbon)···(phenyl plane)} distances (the shortest distance 3.303 Å, the longest 3.624 Å).
22. Similar meso to rac isomerization by UV irradiation was not observed for 2 and 3 at this stage.
23. 2+ or its equivalents by NMR spectroscopic methods failed.
24. No scrambling was observed in the dark. The scrambled products were observed in the initial stage of the irradiation (0.5 h) and gradually increased concomitantly with isomerization of each complex (after 16 h of irradiation, 2/(scrambled complexes, isomer ratio ca. 1/6) = ca. 1/2).
25. Photoassisted exchange of unsaturated hydrocarbon ligands is known, for example: Top, S.; Kaloun, E. B.; Toppi, S.; Herrbach, A.; McGlinchey, M. J.; Jaouen, G. Organometallics 2001, 20, 4554 and references therein.
26. As a possible intramolecular mechanism, two consecutive rotations about one of three C-C single bonds of the tetraene framework would cause a net face-inversion.
27. C-H for coordinated tetraene carbons for 1 are in the range of 153-164 Hz).
28. It has been experimentally and theoretically proved that the electronic state of an assembly of pπ-conjugated molecules depends significantly on the intermolecular space as well as orientation. For selected recent literature: (a) Bartholomew, G. P.: Bazan, G. C. Acc. Chem. Res. 2001, 34, 30. (b) McQuade, D. T.; Kim, J.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 5885. (c) Reitzel, N.; Greve, D. R.; Kjaer, K.; Howes, P. B.; Jayaraman, M.: Savoy, S.; McCullough, R. D.; McDevitt, J. T.; Bjørnholm, T. J. Am. Chem. Soc. 2000, 122, 5788 and references therein. (d) Cornil, J.; dos Santos, D. A.; Crispin, X.; Silbey, R.; Brddas, J. L. J. Am. Chem. Soc. 1998, 120, 1289. (e) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B.-L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.: Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047.
29. It has been experimentally and theoretically proved that the electronic state of an assembly of pπ-conjugated molecules depends significantly on the intermolecular space as well as orientation. For selected recent literature: (a) Bartholomew, G. P.: Bazan, G. C. Acc. Chem. Res. 2001, 34, 30. (b) McQuade, D. T.; Kim, J.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 5885. (c) Reitzel, N.; Greve, D. R.; Kjaer, K.; Howes, P. B.; Jayaraman, M.: Savoy, S.; McCullough, R. D.; McDevitt, J. T.; Bjørnholm, T. J. Am. Chem. Soc. 2000, 122, 5788 and references therein. (d) Cornil, J.; dos Santos, D. A.; Crispin, X.; Silbey, R.; Brddas, J. L. J. Am. Chem. Soc. 1998, 120, 1289. (e) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B.-L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.: Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047.
30. It has been experimentally and theoretically proved that the electronic state of an assembly of pπ-conjugated molecules depends significantly on the intermolecular space as well as orientation. For selected recent literature: (a) Bartholomew, G. P.: Bazan, G. C. Acc. Chem. Res. 2001, 34, 30. (b) McQuade, D. T.; Kim, J.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 5885. (c) Reitzel, N.; Greve, D. R.; Kjaer, K.; Howes, P. B.; Jayaraman, M.: Savoy, S.; McCullough, R. D.; McDevitt, J. T.; Bjørnholm, T. J. Am. Chem. Soc. 2000, 122, 5788 and references therein. (d) Cornil, J.; dos Santos, D. A.; Crispin, X.; Silbey, R.; Brddas, J. L. J. Am. Chem. Soc. 1998, 120, 1289. (e) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B.-L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.: Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047.
31. It has been experimentally and theoretically proved that the electronic state of an assembly of pπ-conjugated molecules depends significantly on the intermolecular space as well as orientation. For selected recent literature: (a) Bartholomew, G. P.: Bazan, G. C. Acc. Chem. Res. 2001, 34, 30. (b) McQuade, D. T.; Kim, J.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 5885. (c) Reitzel, N.; Greve, D. R.; Kjaer, K.; Howes, P. B.; Jayaraman, M.: Savoy, S.; McCullough, R. D.; McDevitt, J. T.; Bjørnholm, T. J. Am. Chem. Soc. 2000, 122, 5788 and references therein. (d) Cornil, J.; dos Santos, D. A.; Crispin, X.; Silbey, R.; Brddas, J. L. J. Am. Chem. Soc. 1998, 120, 1289. (e) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B.-L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.: Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047.
32. It has been experimentally and theoretically proved that the electronic state of an assembly of pπ-conjugated molecules depends significantly on the intermolecular space as well as orientation. For selected recent literature: (a) Bartholomew, G. P.: Bazan, G. C. Acc. Chem. Res. 2001, 34, 30. (b) McQuade, D. T.; Kim, J.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 5885. (c) Reitzel, N.; Greve, D. R.; Kjaer, K.; Howes, P. B.; Jayaraman, M.: Savoy, S.; McCullough, R. D.; McDevitt, J. T.; Bjørnholm, T. J. Am. Chem. Soc. 2000, 122, 5788 and references therein. (d) Cornil, J.; dos Santos, D. A.; Crispin, X.; Silbey, R.; Brddas, J. L. J. Am. Chem. Soc. 1998, 120, 1289. (e) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B.-L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.: Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047.