Structure and magnetism of dinuclear copper(II) metallacyclophanes with oligoacenebis(oxamate) bridging ligands: Theoretical predictions on wirelike magnetic coupling

Journal of the American Chemical Society

Volumn 130, Issue 2, 2008, Pages 576-585

  Pardo, Emilio ^a   Carrasco, Rosa ^c   Ruiz Garcia, Rafael ^a   Julve, Miguel ^a   Lloret, Francesc ^a   Muñoz, M Carmen ^b   Journaux, Yves ^e   Ruiz, Eliseo ^c   Cano, Joan ^c,d  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

^d INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^e SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFERROMAGNETIC MATERIALS; DENSITY FUNCTIONAL THEORY; LIGANDS; MAGNETIC SUSCEPTIBILITY; SELF ASSEMBLY;

DECACENE SPACERS; METALLACYCLOPHANES;

COPPER COMPOUNDS;

ANTHRACENE DERIVATIVE; COPPER DERIVATIVE; CYCLOPHANE DERIVATIVE; ETOMIDATE; LIGAND; NAPHTHALENE; OXAMIC ACID; COPPER; DRUG DERIVATIVE; ETHER DERIVATIVE; N,N' 1,5 NAPHTHALENEBIS(OXAMATE); N,N' 2,6' ANTHRACENEBIS(OXAMATE); N,N'-1,5-NAPHTHALENEBIS(OXAMATE); N,N'-2,6'-ANTHRACENEBIS(OXAMATE); NAPHTHALENE DERIVATIVE; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; MAGNETISM; MEASUREMENT; PREDICTION; THEORETICAL STUDY; CHEMISTRY; SYNTHESIS;

ANTHRACENES; COPPER; ETHERS, CYCLIC; LIGANDS; MAGNETICS; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; OXAMIC ACID;

EID: 40149085767     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0747066     Document Type: Article

References (75)

1. (a) Kahn, O. Molecular Magnetism; VCH Publishers: New York, 1993.
2. (b) Hay, J. P.; Thibeault, J. C.; Hoffmann, R. J. Am. Chem. Soc. 1975, 97, 4884.
3. (c) Kahn, O. Angew. Chem., Int. Ed. Engl. 1985, 24, 834.
4. (d) Magneto-Structural Correlations in Exchange Coupled Systems; Willett, R. D., Gatteschi, D., Kahn, O., Eds.; Reidel: Dordrecht, The Netherlands, 1985.
5. (a) Molecular Electronics; Jorner, J., Ratner, M., Eds.; Blackwell Science: Oxford, 1997.
6. (b) Molecular Electronics: Science and Technology; Aviram, A., Ratner, M., Eds.; Annals of the New York Academy of Sciences: New York, 1998.
7. (c) Joachim, C.; Gimzewski, J. K.; Aviram, A. Nature 2000, 408, 541.
8. (d) Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yaish, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruña, H. D.; McEuen, P. L.; Ralph, D. C. Nature 2002, 417, 722.
9. (e) Liang, W.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Nature 2002, 417, 725.
10. (f) Smith, R. H. M.; Noat, Y.; Untiedt, C.; Lang, N. D.; Van Hemert, M. C.; Van Rultenbeek, J. M. Nature 2002, 419, 906.
11. (g) Ng, M. K.; Lee, D. C.; Yu, L. J. Am. Chem. Soc. 2002, 124, 11862.
12. (h) Carrol, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2002, 41, 4378.
13. (a) Bowler, B. E.; Raphael, A. L.; Gray, H. B. Prog. Inorg. Chem. 1990, 38, 259.
14. (b) Electron Transfer Reactions in Metalloproteins; Sigel, H., Ed.; Metal Ions in Biological Systems, Vol. 27; Marcel Dekker: New York, 1991.
15. (c) Beratan, D. N.; Onuchic, J. N.; Winkler, J. R.; Gray, H. B. Science 1992, 258, 1740.
16. (d) Pelletier, H.; Kraut, J. Science 1992, 258, 1748.
17. (e) Solomon, E. I.; Lowery, M. D. Science 1993, 259, 1575.
18. (f) Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, California, 1994 and references therein.
19. (g) Gamelin, D. R.; Randall, D. W.; Hay, M. T.; Houser, R. P.; Mulder, T. C.; Canters, G. W.; De Vries, S.; Tolman, W. B.; Lu, Y.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 5246.
20. (a) Creutz, C. Prog. Inorg. Chem. 1983, 30, 1.
21. (b) Blondin, G.; Girerd, J. J. Chem. Rev. 1990, 90, 1359.
22. (c) Crutchley, R. J. Adv. Inorg. Chem. 1994, 41, 273.
23. (d) Brunschwig, B. S.; Sutin, N. Coord. Chem. Rev. 1999, 187, 233.
24. (a) McCleverty, J. A.; Ward, M. D. Acc. Chem. Res. 1998, 36, 3447.
25. (b) Launay, J. P. Chem. Soc. Rev. 2001, 30, 386.
26. (a) Bürger, K. S.; Chaudhuri, P.; Wieghardt, K.; Nuber, B. Chem. - Eur. J. 1995, 1, 583.
27. (b) Cargill-Thompson, A. M. W.; Gatteschi, D.; McCleverty, J. A.; Navas, J. A.; Rentschler, E.; Ward, M. D. Inorg. Chem. 1996, 35, 2701.
28. (c) Ung, V. A.; Cargill-Thompson, A. M. W.; Bardwell, D. A.; Gatteschi, D.; Jeffery, J. C.; McCleverty, J. A.; Totti, F.; Ward, M. D. Inorg. Chem. 1997, 36, 3447.
29. (d) Ung, V. A.; Couchman, S. M.; Jeffery, J. C.; McCleverty, J. A.; Ward, M. D.; Totti, F.; Gatteschi, D. Inorg. Chem. 1999, 38, 365.
30. (e) Bayly, S.; McCleverty, J. A.; Ward, M. D.; Gatteschi, D.; Totti, F. Inorg. Chem. 2000, 39, 1288.
31. (f) Fabre, M.; Bonvoisin, J. J. Am. Chem. Soc. 2007, 129, 1434.
32. (a) Bencini, A.; Gatteschi, D.; Totti, F.; Nieto-Sanz, D.; Mc Cleverty, J. A.; Ward, M. D. J. Phys. Chem. A 1998, 102, 10545.
33. (b) Ruiz, E.; Rodríguez-Fortea, A.; Alvarez, S. Inorg. Chem. 2003, 42, 4881.
34. (c) Paital, A. R.; Mitra, T.; Ray, D.; Wong, W. T.; Ribas-Ariño, J.; Novoa, J. J.; Ribas, J.; Aromí, G. Chem. Commun. 2005, 5172.
35. (d) Nunzi, F.; Ruiz, E.; Cano, J.; Alvarez, S. J. Phys. Chem. C 2007, 111, 618.
36. Swiegers, G. F.; Malefetse T. J. Chem. Rev. 2000, 100, 3483.
37. (a) Mederos, A.; Gili, P.; Domínguez, S.; Benítez, A., Palacios, M. S.; Hernández-Padilla, M.; Martín-Zarza, P.; Rodríguez, M. L.; Ruiz-Pérez, C.; Lahoz, F. J.; Oro, L. A.; Brito, F.; Arrieta, J. M.; Vlassi, M.; Germain, G. J. Chem. Soc., Dalton Trans. 1990, 1477.
38. (b) Domínguez, S.; Mederos, A.; Gili, P.; Rancel, A.; Rivera, A. E.; Brito, F.; Lloret, F.; Solans, X.; Ruiz-Pérez, C.; Rodríguez, M. L.; Brito, I. Inorg. Chim. Acta 1997, 255, 367.
39. (a) Bear, C. A.; Waters, J. M.; Waters, T. N. J. Chem. Soc. A 1970, 17, 2494.
40. (b) Jeter, D. Y.; Hatfield, W. E. Inorg. Chim. Acta 1972, 6, 440.
41. (c) Hernández-Molina, R.; Mederos, A.; Gili, P.; Domínguez, S.; Lloret, F.; Cano, J.; Julve, M.; Ruiz-Pérez, C.; Solans, X. J. Chem. Soc., Dalton Trans. 1997, 4327.
42. (d) Paital, A. R.; Mitra, T.; Ray, D.; Wong, W. T.; Ribas-Ariño, J.; Novoa, J. J.; Ribas, J.; Aromí, G. Chem. Commun. 2005, 5172.
43. (e) Paital, A. R.; Wu, A. Q.; Guo, G. G.; Aromí, G.; Ribas-Ariño, J.; Ray, D. Inorg. Chem. 2007, 46, 2947.
44. (f) Vázquez, M.; Taglietti, A.; Gatteschi, D.; Sorace, L.; Sangregorio, C.; González, A. M.; Maneiro, M.; Pedrido, R. M.; Bermejo, M. R. Chem. Commun. 2003, 1840.
45. (a) Inoue, M. B.; Velázquez, E. F.; Medrano, F.; Ochoa, K. L.; Gálvez, J. C.; Inoue, M.; Fernando, Q. Inorg. Chem. 1998, 37, 4070.
46. (b) Inoue, M. B.; Muñoz, I. C.; Machi, L.; Inoue, M.; Fernando, Q. Inorg. Chim. Acta 2000, 311, 50.
47. (c) Inoue, M. B.; Inoue, M.; Sugich-Miranda, R.; Machi, L.; Velázquez, E. F.; Fernando, Q. Inorg. Chim. Acta 2001, 317, 181.
48. (d) Mosina, L. V.; Raitsimring, A. V.; Inoue, M. B.; Fernando, Q.; Inoue, M. Appl. Magn. Reson. 2001, 20, 249.
49. (a) Fernández, I.; Ruiz, R.; Faus, J.; Julve, M.; Lloret, F.; Cano, J.; Ottenwaelder, X.; Journaux, Y.; Muñoz, M. C. Angew. Chem., Int. Ed. 2001, 40, 3039.
50. (b) Pardo, E.; Faus, J.; Julve, M.; Lloret, F.; Muñoz, M. C.; Cano, J.; Ottenwaelder, X.; Journaux, Y.; Carrasco, R.; Blay, G.; Fernández, I.; Ruiz-García, R. J. Am. Chem. Soc. 2003, 125, 10770.
51. (a) Clar, E. Polycyclic Hydrocarbons; Academic Press: London, U.K., 1964; Vols. 1 and 2.
52. (b) Geens, Y.; Klärner, G.; Müllen, K. In Electronic Materials: The Oligomer Approach; Müllen, K., Klärner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 48.
53. (a) Bendikov, M.; Duong, H. M.; Starkey, K.; Houk, K. N.; Carter, E. A.; Wudl, F. J. Am. Chem. Soc. 2004, 126, 7416.
54. (b) Norton, J. E.; Houk, K. N. J. Am. Chem. Soc. 2005, 127, 4162.
55. Preliminary DFT energy calculations on the related dinuclear copper(II) model complexes with single α,α′- and β,β′- disubstituted oligoacenebis-(oxamate) bridging ligands show a singlet spin ground state lying well below the triplet excited state in all cases. In both series, the calculated - J value decreases with the number of benzenoid repeating units for n = 1-3, and then it increases continuously for n = 4-10 as a result of the open-shell singlet diradical character of the oligoacene spacers (data reported elsewhere).
56. Rabjohns, M. A.; Hodge, P.; Lovell, P. A. Polymer 1997, 38, 3395.
57. (a) Sheldrick, G. M. SHELX97, Programs for Crystal Structure Analysis (release 97-2); Institut für Anorganische Chemie der Universität: Göttingen, Germany, 1998.
58. (b) Hooft, R. W. W. COLLECT; Nonius BV: Delft, The Netherlands, 1999.
59. (c) Duisenberg, A. J. M.; Kroon-Batenburg, L. M. J.; Schreurs, A. M. M. J. Appl. Crystallogr. 2003, 36, 220 (EVALCCD).
60. (d) SADABS, version 2.03; Bruker AXS Inc.: Madison, WI, 2000.
61. (e) Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837 (WINGX).
62. (f) Nardelli, M. J. Appl. Crystallogr. 1995, 28, 659.
63. (g) Palmer, D. CrystalMaker, version 7.2; Cambridge University Technical Services: Cambridge, U.K., 2007.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
65. (a) Ruiz, E.; Alemany, P.; Alvarez, S.; Cano, J. J. Am. Chem. Soc. 1997, 119, 1297.
66. (b) Ruiz, E.; Cano, J.; Alvarez, S.; Alemany, P. J. Am. Chem. Soc. 1998, 120, 11122.
67. (c) Ruiz, E.; Cano, J.; Alvarez, S.; Alemany, P. J. Comput. Chem. 1999, 20, 1391.
68. (d) Ruiz, E.; Rodriguez-Fortea, A.; Cano, J.; Alvarez, S.; Alemany, P. J. Comput. Chem. 2003, 24, 982.
69. (e) Ruiz, E.; Polo, V.; Cano, J.; Alvarez, S. J. Chem. Phys. 2005, 123, 164110.
70. Frisch, M. J. et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
71. (a) Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
72. (b) Schaefer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
73. (a) Carpenter, J. E.; Weinhold, F. J. Mol. Struct. 1988, 169, 41.
74. (b) Reed, A. E.; Curtis, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
75. (c) Weinhold, F.; Carpenter, J. E. The Structure of Small Molecules and Ions; Plenum: 1988; p 227.