Supramolecular Photomagnetic Materials: Photoinduced Dimerization of Ferrocene-Based Polychlorotriphenylmethyl Radicals

Chemistry - A European Journal

Volumn 10, Issue 3, 2004, Pages 603-616

  Ratera, Imma ^a   Ruiz Molina, Daniel ^a   Vidal Gancedo, José ^a   Novoa, Juan J ^b   Wurst, Klaus ^c   Letard, Jean François ^d   Rovira, Concepció ^a   Veciana, Jaume ^a  

^a INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITY OF INNSBRUCK   (Austria)

^d INST CHIM MATIERE COND BORDEAUX   (France)

Author keywords

Cis trans isomerization; Ferrocene; Photomagnetism; Self assembly; Triphenylmethyl radical

Indexed keywords

ANTIFERROMAGNETIC MATERIALS; DIMERIZATION; DISCRETE FOURIER TRANSFORMS; FREE RADICALS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BONDS; ISOMERIZATION; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS; PHOTOCHEMICAL REACTIONS; SELF ASSEMBLY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

PHOTOINDUCED ISOMERIZATION; PHOTOMAGNETIC MATERIALS;

SUPRAMOLECULAR CHEMISTRY;

FERROCENE DERIVATIVE; POLYCHLOROTRIPHENYLMETHYL RADICAL; RADICAL; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DENSITY FUNCTIONAL THEORY; DIMERIZATION; ELECTRON SPIN RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; MAGNETISM; MOLECULAR DYNAMICS; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 1242345166     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305194     Document Type: Article

References (83)

1. a) M. Verdaguer, Science 1996, 272, 698.
2. a) P. Gütlich, A. Hauser, H. Spiering, Angew. Chem. 1994, 106, 2109; Angew. Chem. Int. Ed. Engl. 1994, 33, 2024 and references therein;
3. a) P. Gütlich, A. Hauser, H. Spiering, Angew. Chem. 1994, 106, 2109; Angew. Chem. Int. Ed. Engl. 1994, 33, 2024 and references therein;
4. b) K. Nagai, T. Iyoda, A. Fujishima, K. Hashimoto, Solid State Commun. 1997, 102, 809.
5. S. Nakatsuji, M. Mizumoto, A. Takai, H. Akutsu, J. Yamada, H. Kawamura, S. Schmitt, K. Hafner, Mol. Cryst. Liq. Cryst. 2000, 348, 1.
6. a) K. Hamachi, K. Matsuda, T. Itoh, H. Iwamura, Bull. Chem. Soc. Jpn. 1998, 71, 2937;
7. b) K. Matsuda, M. Irie, Chem. Lett. 2000, 16;
8. c) K. Matsuda, M. Irie, Tetrahedron Lett. 2000, 41, 2577.
9. a) S. Nakatsuji, Y. Ogawa, S. Takeuchi, H. Akutsu, J. Yamada, A. Naito, K. Sudo, N. Yasuoka, J. Chem. Soc. Perkin Trans. 1 2000, 2, 1969;
10. b) T. Ojima, H. Akutsu, J. Yamada, S. Nakatsuji, Chem. Lett. 2000, 918;
11. c) S. Takeuchi, Y. Ogawa, A. Naito, K. Sudo, N. Yasuoka, H. Akutsu, J. Yamada, S. Nakatsuji, Mol. Cryst. Liq. Cryst. 2000, 345, 167.
12. a) K. Matsuda, M. Irie, J. Am. Chem. Soc. 2000, 122, 7195;
13. b) K. Matsuda, M. Irie, J. Am. Chem. Soc. 2000, 122, 8309;
14. c) T. Ojima, H. Akutsu, J. Yamada, S. Nakatsuji, Polyhedron 2001, 20, 1335;
15. d) S. Karasawa, N. Koga, Polyhedron 2001, 20, 1387.
16. a) O. Sato, T. Iyoda, A. Fujishima, K. Hashimoto, Science 1996, 272, 704;
17. b) V. Escax, A. Bleuzen, C. Cartier dit Moulin, F. Villain, A. Goujon, F. Varret, M. Verdaguer, J. Am. Chem. Soc. 2001, 123, 12 536.
18. a) Renz, H. Oshio, V. Ksenofontov, M. Waldeck, H. Spiering, P. Gütlich, Angew. Chem. 2000, 112, 3832; Angew. Chem. Int. Ed. 2000, 39, 3699;
19. a) Renz, H. Oshio, V. Ksenofontov, M. Waldeck, H. Spiering, P. Gütlich, Angew. Chem. 2000, 112, 3832; Angew. Chem. Int. Ed. 2000, 39, 3699;
20. c) P. Gütlich, Y. García, T. Woike, Coord. Chem. Rev. 2001, 219-221, 839.
21. D. Ruiz-Molina, J. Veciana, K. Wurst, D. N. Hendrickson, C. Rovira, Inorg. Chem. 2000, 39, 617.
22. W. Sander, G. Bucher, F. Reichel, D. Cremer, J. Am. Chem. Soc. 1991, 113, 5311.
23. L. C. Bush, R. B. Heath, J. A. Berson, J. Am. Chem. Soc. 1993, 115, 9830.
24. a) K. Matsuda, M. Irie, Tetrahedron Lett. 2000, 41, 2577;
25. K. Matsuda, M. Irie, Chem. Lett. 2000, 16.
26. K. Hamachi, K. Matsuda, T. Itoh, H. Iwamura, Bull. Chem. Soc. Jpn. 1998, 71, 2937.
27. S. Karasawa, H. Kumada, N. Koga, H. Iwamura, J. Am. Chem. Soc. 2001, 123, 9685.
28. S. De Feyter, A. Gesquière, K. Wurst, D. B. Amabilino, J. Veciana, F. C. De Schryver, Angew. Chem. 2001, 113, 3317; Angew. Chem. Int. Ed. 2001, 40, 3217.
29. S. De Feyter, A. Gesquière, K. Wurst, D. B. Amabilino, J. Veciana, F. C. De Schryver, Angew. Chem. 2001, 113, 3317; Angew. Chem. Int. Ed. 2001, 40, 3217.
30. a) Magnetic Properties of Organic Materials (Ed.: P. M. Lahti), Marcel Dekker, NY, 1999, Academic, Dordrecht, 1999;
31. b) Magneto Science: Molecules to Materials Vols. 1 and 2 (Eds.: J. Miller, M. Drillon), Wiley-VCH, 2001;
32. c) Supramolecular Engineering of Synthetic Metallic Materials (Eds.: J. Veciana, C. Rovira, D. B. Amabilino,) NATO ASI Series, Vol. 518, 1998
33. a) J. Veciana, J. Cirujeda, C. Rovira, J. Vidal-Gancedo, Adv. Mater. 1995, 7, 221;
34. b) E. Hernàndez, M. Mas, E. Molins, C. Rovira, J. Veciana, Angew. Chem. 1993, 105, 919. Angew. Chem. Int. Ed. Engl. 1993, 32, 882;
35. b) E. Hernàndez, M. Mas, E. Molins, C. Rovira, J. Veciana, Angew. Chem. 1993, 105, 919. Angew. Chem. Int. Ed. Engl. 1993, 32, 882;
36. c) J. Cirujeda, L. E. Ochando, J. M. Amigó, C. Rovira, J. Rius, J. Veciana, Angew. Chem. 1995, 107, 99. Angew. Chem. Int. Ed. Engl. 1995, 34, 55;
37. c) J. Cirujeda, L. E. Ochando, J. M. Amigó, C. Rovira, J. Rius, J. Veciana, Angew. Chem. 1995, 107, 99. Angew. Chem. Int. Ed. Engl. 1995, 34, 55;
38. c) M. M. Matsushita, A. Izuoka, T. Sugawara, T. Kobayashi, N. Wada, K. Takeda, M. Ishikawa, J. Am. Chem. Soc. 1997, 119, 4369;
39. d) A. Caneschi, F. Ferraro, D. Gatteschi, A. Le Lirzin, M. Novak, E. Rentschler, R. Sessoli, Adv. Mater. 1995, 7, 476;
40. e) F. M. Romero, R. Ziessel, M. Drillon, J.-L. Tholence, C. Paulsen, N. Kyritsakas, J. Fischer, Adv. Mater. 1996, 8, 826.
41. a) H. M. McConnell, J. Chem. Phys. 1963, 33, 1910;
42. b) R. Breslow, B. Jaun, R. Q. Klutiz, C. Z. Xia, Tetrahedron 1981, 37, 863;
43. c) J. Zhang, M. Baumgarten, Chem. Phys. 1997, 222, 1.
44. a) K. E. Vostrikova, D. Luneau, W. Wernsdorfer, P. Rey, M. Verdaguer, J. Am. Chem. Soc. 2000, 122, 718;
45. b) C. Rancurel, D. B. Leznoff, J.-P. Sutter, S. Golhen, L. Ouahab, J. Kliava, O. Kahn, Inorg. Chem. 1999, 38, 4753;
46. c) M. Tanaka, K. Matsuda, T. Itoh, H. Iwamura, Angew. Chem. 1998, 110, 866. Angew. Chem. Int. Ed. 1998, 37, 810;
47. c) M. Tanaka, K. Matsuda, T. Itoh, H. Iwamura, Angew. Chem. 1998, 110, 866. Angew. Chem. Int. Ed. 1998, 37, 810;
48. d) A. Caneschi, D. Gatteschi, P. Rey, Prog. Inorg. Chem. 1991, 39, 331, and references therein.
49. a) N. Hirota, S. I. Weisssman, J. Am. Chem. Soc. 1964, 86, 2538;
50. b) M. Baumgarten, L. Gherghel, T. Wehrmeister, Chem. Phys. Lett. 1997, 267, 175, and references therein.
51. B. N. Figgis, E. S. Kucharski, M. Vrtis, J. Am. Chem. Soc. 1993, 115, 176; and references therein.
52. Preliminary results were presented in a communication: I. Ratera, D. Ruiz-Molina, J. Vidal-Gancedo, K. Wurst, N. Daro, J.-F. Letard, C. Rovira, J. Veciana, Angew. Chem. 2001, 113, 933; Angew. Chem. Int. Ed. 2001, 40, 919.
53. Preliminary results were presented in a communication: I. Ratera, D. Ruiz-Molina, J. Vidal-Gancedo, K. Wurst, N. Daro, J.-F. Letard, C. Rovira, J. Veciana, Angew. Chem. 2001, 113, 933; Angew. Chem. Int. Ed. 2001, 40, 919.
54. K. Maeda, E. Fisher, J. Israel Chem. 1977, 16, 294.
55. L. Teruel, Ll. Viadel, J. Carilla, Ll. Fajarí, E. Brillas, J. Sane, J. Rius, L. Juliá, J. Org. Chem. 1996, 61, 6063.
56. 2 = 0.0703. CCDC-147245 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.can.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (+44)1223-336033; or deposit@ccdc.cam.ac.uk).
57. A systematic search of the Cambridge Crystallographic Structure Database (CSD) revealed the existence of several examples of imino derivatives in which the -H-C=N- group adopts a trans configuration. There is no example of the same group adopting a cis configuration. This agrees with the experimental difficulties found in this work in attempts to crystallize the cis isomer.
58. (TOTAL) given by the sum of the orbital energies. This is usually the case in open shell systems with many states in a small energy window, as is the case in transition metal complexes, among others.
59. The calculations were done at the B3LYP/LANL2DZ level.
60. R. S. Mulliken, J. Chem. Phys. 1955, 23, 1833.
61. 2)- is now coplanar, instead of presenting an out-of-plane dihedral of 49.1° caused by the steric effects produced by the bulky Cl atoms at the ortho positions.
62. For radical 1 we computed the potential energy curve for values of the θ angle at the lower (θ=0-180°) and upper (θ=180-360°) regions, which were found to be nearly symmetric. In order to reduce the computational costs, we only computed half of the potential energy curve for radical 2, the lower region(θ=0-180°).
63. Photochemistry and Photophysics, Vol. 2 (Ed.: J. F. Rabek), CRC Press, Boca Raton, 1990, Chapter 4.
64. C. Rovira, D. Ruiz-Molina, O. Elsner, J. Vidal-Gancedo, J. Bonvoisin, J.-P. Launay, J. Veciana, Chem. Eur. J. 2001, 7, 240.
65. a) D. R. Scott, R. S. Becker, J. Chem. Phys. 1962, 35, 516;
66. b) D. R. Scott, R. S. Becker, J. Chem. Phys. 1962, 35, 2246.
67. In fact, similar intervalence transition bands have already been observed in mixed-valance complexes containing ferrocenylpyridines. See: T.-Y. Liu, Y. J. Chen, C.-C. Tai, K. S. Kwan, Inorg. Chem. 1999, 38, 674.
68. S. Barlow, H. E. Bunting, C. Ringham, J. C. Green, G. U. Bublitz, S. G. Boxer, J. W. Perry, S. R. Marder, J. Am. Chem. Soc. 1999, 121, 3715.
69. J. Armet, C. Veciana, J. Rovira, J. Riera, E. Castañer, J. Molins, C. Rius, S. Miravitlles, J. Olivella, Brichfeus, J. Phys. Chem. 1987, 91, 5608.
70. 14N nuclei is remarkable, providing evidence that the unpaired electron is not only delocalized in the triphenylmethyl unit but also into the imine group. This fact is expected to enhance the presence of intermolecular magnetic exchange interactions in the case that -CH=N- groups are involved in intermolecular bonds; as it was confirmed by ESR frozen solution experiments for the cis-1 isomer.
71. O. Elsner, D. Ruiz-Molina, J. Vidal-Gancedo, C. Rovira, J. Veciana, Chem. Comun. 1999, 579.
72. I. Ratera, D. Ruiz-Molina, F. Renz, J. Ensling, K. Wurst, C. Rovira, P. Gütlich, J. Veciana, J. Am. Chem. Soc. 2003, 125, 1462-1463.
73. The |D′| parameter reflects primarily the mean distance between the interacting electrons and the |E′| parameter depends mostly on the symmetry of the spin density distribution.
74. The simulation was carried out by superposition of two spectra, one characteristic of a symmetric triplet species, from where the absolute values of the zero-field splitting parameters were obtained, and another consisting of a single broad line characteristic of a monoradical species, which is associated to the fraction of the radicals that remain in solution as monomers (4%).
75. S. D. Mcglynn, T. Azumi, M. Kinoshita in Molecular Spectroscopy of the Triplet State, Prentice Hall, New Jersey, 1969.
76. 14N nuclei for radical trans-1, providing evidence that the unpaired electron is not only delocalized in the triphenylmethyl unit but also into the imine group. This fact is expected to enhance the presence of intermolecular magnetic exchange interactions within the -C=N- groups involved in the intermolecular bonds.
77. R. L. Carlin, Magnetochemistry, Springer, Berlin, 1986, 71.
78. trans-1→cis-1 isomerization was photoinduced for radical 1 using an irradiation lamp with an interference filter centered at 415 nm (bandwidth 60 nm). No evidence of cis-1→trans-1 isomerization was observed by using various interference filters (centered from 350 to 450 nm).
79. This fact is an indication of the larger degree of conjugation for isomer trans-1 over isomer cis-1.
80. N. R. King, E. A. Whale, F. J. Davis, A. Gilbert, G. J. Mitchell, J. Mater. Chem. 1997, 7, 625.
81. It is worth noting that at 20°C in a degassed solution and in the dark both isomers are stable for more than five hours.
82. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902.
83. C. Zou, M. S. Wrighton, J. Am. Chem. Soc. 1990, 112, 7578.