Synthesis and properties of dinuclear complexes with a photochromic bridge: An intervalence electron transfer switching 'on' and 'off

European Journal of Inorganic Chemistry

Volumn , Issue 7, 2000, Pages 1581-1590

  Fraysse, Sandrine ^a   Coudret, Christophe ^a   Launay, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

Electron transfer; Metallacycles; Molecular devices; Photochromism

Indexed keywords

ELECTRON TRANSITIONS; MOLECULAR ORBITALS; ORBITAL CALCULATIONS; OXIDATION; RUTHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

CLOSED FORM; DITHIENYLETHENE; ELECTRON TRANSFER; ELECTRONIC COUPLING; INTERVALENCE TRANSITION; METALLACYCLES; MOLECULAR DEVICE; NORBORNADIENE; PHOTOCHROMICS; QUADRICYCLANES;

PHOTOCHROMISM;

METAL COMPLEX; RUBIDIUM;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; ISOMERISM; PHOTOCHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033940482     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0682(200007)2000:7<1581::AID-EJIC1581>3.0.CO;2-2     Document Type: Article

References (59)

1. [1a] For an overview of molecular electronics see, for instance: Molecular Electronics: Science and Technology (Eds.: A. Aviram, M. Ratner), Annals NY Acad. Sci. 1998, 852, and references therein.
2. [1b] C. Joachim, J. K. Gimzewski, Chem. Phys. Lett. 1997, 265, 353.
3. [1c] A. Gourdon, H. Tang, in Molecular Electronics: Science and Technology (Eds.: A. Aviram, M. Ratner), Annals NY Acad. Sci. 1998, 852, p. 219.
4. [1d] V. J. Langlais, R. R. Schlittler, H. Tang, A. Gourdon, C. Joachim, J. K. Gimzewski, Phys. Rev. Lett. 1999, 83, 2809.
5. [2a] C. Patoux, J.-P. Launay, M. Beley, S. Chodorowski-Kimmes, J.-P. Collin, S. James, J.-P. Sauvage, J. Am. Chem. Soc. 1998, 120, 3717.
6. [2b] C. Patoux, C. Coudret, J.-P. Launay, C. Joachim, A. Gourdon, Inorg. Chem. 1997, 36, 5037.
7. [2c] A.-C. Ribou, J.-P. Launay, M. L. Sachtleben, H. Li, C. W. Spangler, Inorg. Chem. 1996, 35, 3735.
8. [2d] A.-C. Ribou, J.-P. Launay, K. Takahashi, T. Nihira, S. Tarutani, C. W. Spangler, Inorg. Chem. 1994, 33, 1325.
9. [2e] C. Creutz, Progr. Inorg. Chem. 1983, 30, 1, and references therein.
10. N. S. Hush, Progr. Inorg. Chem. 1967, 8, 391; N. S. Hush, Coord. Chem. Rev. 1985, 64, 135.
11. N. S. Hush, Progr. Inorg. Chem. 1967, 8, 391; N. S. Hush, Coord. Chem. Rev. 1985, 64, 135.
12. P. Lainé, V. Marvaud, A. Gourdon, J.-P. Launay, R. Argazzi, C.-A. Bignozzi, Inorg. Chem. 1996, 35, 711.
13. M. Irie, M. Mohri, J. Org. Chem. 1988, 53, 803. M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc., Chem. Commun. 1992, 206; M. Irie, O. Miyatake, K. Uchida, J. Am. Chem. Soc. 1992, 114, 8715.
14. M. Irie, M. Mohri, J. Org. Chem. 1988, 53, 803. M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc., Chem. Commun. 1992, 206; M. Irie, O. Miyatake, K. Uchida, J. Am. Chem. Soc. 1992, 114, 8715.
15. M. Irie, M. Mohri, J. Org. Chem. 1988, 53, 803. M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc., Chem. Commun. 1992, 206; M. Irie, O. Miyatake, K. Uchida, J. Am. Chem. Soc. 1992, 114, 8715.
16. [6a] S. L. Gilat, S. H. Kawai, J.-M. Lehn, J. Chem. Soc., Chem. Commun. 1993, 1439.
17. [6b] S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275.
18. [6c] S. H. Kawai, S. L. Gilat, R. Ponsinet, R.: J.-M. Lehn, Chem. Eur. J. 1995, 1, 285.
19. [6d] S. H. Kawai, S. L. Gilat, J.-M. Lehn, Eur. J. Org. Chem. 1999, 2359.
20. [6e] G. M. Tsivgoulis, J.-M. Lehn, Chem. Eur. J. 1996, 2, 1399.
21. M. Beley, S. Chodorowski-Kimmes, J.-P. Collin, P. Lainé, J.-P. Launay, J.-P. Sauvage, Angew. Chem. Int. Ed. Engl. 1994, 33, 1775.
22. J.-P. Sutter, D. M. Grove, M. Beley, J.-P. Collin, N. Veldman, A. L. Spek, J.-P. Sauvage, G. Van Koten, Angew. Chem. Int. Ed. Engl. 1994, 33, 1282.
23. C. Coudret, S. Fraysse, J.-P. Launay, Chem. Commun. 1998, 663.
24. S. Fraysse, C. Coudret, J.-P. Launay, Tetrahedron Lett. 1998, 39, 7873.
25. M. Magoga, C. Joachim, Phys. Rev. B 1997, 56, 4722.
26. Metal-Catalysed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, chapter 5.
27. P. Stang, V. Zhdankin, J. Am. Chem. Soc. 1991, 113, 4571.
28. P. Stang, A. Schwarz, T. Blume, V. Zhdankin, Tetrahedron Lett. 1992, 33, 6759.
29. P. Stang, A. Schwarz, V. Zhdankin, Synthesis 1993, 35.
30. T. Saika, M. Irie, T. Shimidzu, J. Chem. Soc., Chem. Commun. 1994, 2123.
31. S. Kobatake, T. Yamada, K. Uchida, N. Kato, M. Irie, J. Am. Chem. Soc. 1999, 121, 2380.
32. B. P. Warner, S. L. Buchwald, J. Org. Chem. 1994, 59, 5822.
33. J. K. Stille, J. H. Simpson, J. Am. Chem. Soc. 1987, 109, 2138.
34. A related example of a Glaser-like reaction involving an organic halide as oxidizer was reported: M. E. Wright, C. K. Lowe-Ma, Organometallics 1990, 9, 347.
35. R. Durr, S. Cossu, O. De Lucchi, Synth. Commun. 1997, 27, 1369.
36. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 50, 4467.
37. 2-like terminal units, no consequences of the chirality of the metal centers were reported, neither on the NMR spectra (J. Bolger, A. Gourdon, E. Ishow, J.-P. Launay, Inorg. Chem. 1996, 35, 2937), nor on the electrochemical and spectroscopic behavior ( M. J. Powers, T. J. Meyer, J. Am. Chem. Soc. 1980, 102, 1289; A. C. Benniston, V. Goulle, A. Harriman, J.-M. Lehn, B. Marczinke, J. Phys. Chem. 1994, 98, 7798). See also the review: R. J. Crutchley, Adv. Inorg. Chem. 1994, 41, 273, and references therein. Thus, the stereochemical aspects are not considered in the rest of this paper.
38. 2-like terminal units, no consequences of the chirality of the metal centers were reported, neither on the NMR spectra (J. Bolger, A. Gourdon, E. Ishow, J.-P. Launay, Inorg. Chem. 1996, 35, 2937), nor on the electrochemical and spectroscopic behavior ( M. J. Powers, T. J. Meyer, J. Am. Chem. Soc. 1980, 102, 1289; A. C. Benniston, V. Goulle, A. Harriman, J.-M. Lehn, B. Marczinke, J. Phys. Chem. 1994, 98, 7798). See also the review: R. J. Crutchley, Adv. Inorg. Chem. 1994, 41, 273, and references therein. Thus, the stereochemical aspects are not considered in the rest of this paper.
39. 2-like terminal units, no consequences of the chirality of the metal centers were reported, neither on the NMR spectra (J. Bolger, A. Gourdon, E. Ishow, J.-P. Launay, Inorg. Chem. 1996, 35, 2937), nor on the electrochemical and spectroscopic behavior ( M. J. Powers, T. J. Meyer, J. Am. Chem. Soc. 1980, 102, 1289; A. C. Benniston, V. Goulle, A. Harriman, J.-M. Lehn, B. Marczinke, J. Phys. Chem. 1994, 98, 7798). See also the review: R. J. Crutchley, Adv. Inorg. Chem. 1994, 41, 273, and references therein. Thus, the stereochemical aspects are not considered in the rest of this paper.
40. 2-like terminal units, no consequences of the chirality of the metal centers were reported, neither on the NMR spectra (J. Bolger, A. Gourdon, E. Ishow, J.-P. Launay, Inorg. Chem. 1996, 35, 2937), nor on the electrochemical and spectroscopic behavior ( M. J. Powers, T. J. Meyer, J. Am. Chem. Soc. 1980, 102, 1289; A. C. Benniston, V. Goulle, A. Harriman, J.-M. Lehn, B. Marczinke, J. Phys. Chem. 1994, 98, 7798). See also the review: R. J. Crutchley, Adv. Inorg. Chem. 1994, 41, 273, and references therein. Thus, the stereochemical aspects are not considered in the rest of this paper.
41. -1]): open form (12a): 306 (61250); closed form (12b): 604 (21900).
42. 8, i.e., 0.0205.
43. A. T. Bens, D. Frewert, K. Kodatis, C. Kryschi, H.-D. Martin, H. P. Trommsdorff, Eur. J. Org. Chem. 1998, 2333.
44. J. Lacour, S. Torche-Haldimann, J. J. Jodry, C. Ginglinger, F. Favarger, Chem. Commun. 1998, 1733; J. Lacour, S. Barchéchath, J. J. Jodry, C. Ginglinger, Tetrahedron Lett. 1998, 39, 567.
45. J. Lacour, S. Torche-Haldimann, J. J. Jodry, C. Ginglinger, F. Favarger, Chem. Commun. 1998, 1733; J. Lacour, S. Barchéchath, J. J. Jodry, C. Ginglinger, Tetrahedron Lett. 1998, 39, 567.
46. M. Irie, K. Sakemura, M. Okinaka, K. Uchida, J. Org. Chem. 1995, 60, 8305.
47. A related example of ring opening upon oxidation was described: C. Pac, Pure Appl. Chem. 1986, 58, 1249. C. Pac, J. Photochem. Photobiol. A 1987, 41, 37. It involves a photoinduced oxidation of a strained carbocycle (cyclobutane) by a sensitizer, resulting in bond cleavage in the former. For another case of ring reopening by photoinduced electron transfer, see: T. Carell, R. Epple, V. Gramlich, Angew. Chem. Int. Ed. Engl. 1996, 35, 620.
48. A related example of ring opening upon oxidation was described: C. Pac, Pure Appl. Chem. 1986, 58, 1249. C. Pac, J. Photochem. Photobiol. A 1987, 41, 37. It involves a photoinduced oxidation of a strained carbocycle (cyclobutane) by a sensitizer, resulting in bond cleavage in the former. For another case of ring reopening by photoinduced electron transfer, see: T. Carell, R. Epple, V. Gramlich, Angew. Chem. Int. Ed. Engl. 1996, 35, 620.
49. A related example of ring opening upon oxidation was described: C. Pac, Pure Appl. Chem. 1986, 58, 1249. C. Pac, J. Photochem. Photobiol. A 1987, 41, 37. It involves a photoinduced oxidation of a strained carbocycle (cyclobutane) by a sensitizer, resulting in bond cleavage in the former. For another case of ring reopening by photoinduced electron transfer, see: T. Carell, R. Epple, V. Gramlich, Angew. Chem. Int. Ed. Engl. 1996, 35, 620.
50. R. Weiss, J. Seubert, Angew. Chem. Int. Ed. Engl. 1994, 33, 891.
51. Cerius2, Biosym/Molecular Simulations, San Diego, CA, USA.
52. CACAO PC Version 4.0, July 1994. C. Mealli, D. M. Proserpio, J. Chem. Educ. 1990, 67, 399.
53. CACAO PC Version 4.0, July 1994. C. Mealli, D. M. Proserpio, J. Chem. Educ. 1990, 67, 399.
54. J.-P. Launay, S. Fraysse, C. Coudret, Mol. Cryst. Liq. Cryst., in press.
55. A. Altomare, G. Cascarano, G. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, "SIR92 - a program for automatic solution of crystal structures by direct methods", J. Appl. Crystallogr. 1994, 27, 435.
56. D. J. Watkin, C. K. Prout, J. R. Carruthers, P. W. Betteridge, R. I. Cooper, CRYSTALS Issue 11, Chemical Crystallography Laboratory, University of Oxford, Oxford (UK).
57. ORTEP III: L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
58. K. H. Pausacker, J. Chem. Soc. 1953, 107.
59. A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard, W. M. Skiff, J. Am. Chem. Soc. 1992, 114, 10024.