Novel dissymmetric tetrathiafulvalenes as precursors of organic metals: Synthesis, x-ray crystal structures, electrochemical properties and study of their radical cations

European Journal of Organic Chemistry

Volumn , Issue 16, 2000, Pages 2867-2875

  Ribera, Elisabet ^a   Veciana, Jaume ^a   Molins, Elies ^a   Mata, Ignasi ^a   Wurst, Klaus ^b   Rovira, Concepció ^a  

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

^b UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

Conducting materials; Crystal engineering; EPR spectroscopy; Organic conductors; Radical ions; Tetrathiafulvalenes

Indexed keywords

CATION; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; HYDROGEN BOND; SPECTROSCOPY; SYNTHESIS; X RAY ANALYSIS;

EID: 0033840072     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200008)2000:16<2867::AID-EJOC2867>3.0.CO;2-W     Document Type: Article

References (51)

1. J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geiser, H. H. Wang, A. M. Kini, M. H. Whangbo, Organic Superconductors (Including Fullerenes). Synthesis, Structure, Properties and Theory: Prentice Hall, Englewood Cliffs, NJ, 1992.
2. J. M. Williams, A. M. Kini, H. H. Wang, K. D. Carlson, U. Geiser, L. K. Montgomery, G. J. Pyrca, D. M. Watkins, J. M. Kommers, S. J. Boryschuk, A. V. S. Crouch, W. K. Kwok, J. E. Schirber, D. L. Overmyer, D. Jung, M.-H. Whangbo, Inorg. Chem. 1990, 29, 3262.
3. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
4. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
5. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
6. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
7. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
8. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
9. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
10. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
11. Reviews: [3a] A. Krief, Tetrahedron 1986, 42, 1209. [3b] M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355. [3c] D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr, M. Mays, Phosphorous Sulfur Silicon 1992, 67, 277. [3d] G. Schukat, E. Fanghänel, Sulfur Rep. 1993, 14, 245. [3e] M. Adam, K. Müllen, Adv. Mater. 1994, 6, 439-459. [3f] .J. Garín, Adv. Heterocycl. Chem. 1995, 62, 249-304. [3g] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481. [3h] T. Otsubo, Y. Aso, K. Takimiya, Adv. Mater. 1996, 8, 203. [3i] G. Schukat, E. Fanghänel, Sulfur Rep. 1996, 18, 1.
12. C. Rovira, J. Veciana, N. Santaló, J Tarrés, J. Cirujeda, E. Molins, J. Llorca, E. Espinosa, J. Org. Chem. 1994, 59, 3307.
13. A. Pérez-Benítez, J. Tarrés, E. Ribera, J. Veciana, C. Rovira, Synthesis 1999, 577.
14. T. Jigami, K. Takimiya, T. Otsubo, Y. Aso, J. Org. Chem. 1998, 63, 8865.
15. [7a] J. Tarrés, N. Santaló, M. Mas, E. Molins, J. Veciana, C. Rovira, S. Yang, H. Lee, D. O. Cowan, M.-L. Doublet, E. Canadell, Chem. Mater. 1995, 7, 1558.
16. [7b] E. Ribera, C. Rovira, J. Veciana, V. N. Laukhin, E. Canadell, J. Vidal-Gancedo, E. Molins, Synth. Met. 1997, 86, 1993.
17. [7c] C. Rovira, J. Veciana, J. Tarrés, E. Molins, M. Mas, D. O. Cowan, S. Yang, Synth. Met. 1995, 70, 883.
18. [7d] C. Rovira, J. Tarrés, E. Ribera, J. Veciana, E. Canadell, E. Molins, M. Mas, V. Laukhin, M.-L. Doublet, D. O. Cowan, S. Yang, Synth. Met. 1997, 86, 2145-2146.
19. [7e] J. Tarrés, J. Veciana, C. Rovira, Synth. Met. 1995, 70, 1167.
20. [7f] E. Coronado, L. R. Falvello, J. R. Galán-Mascarós, C. Giménez-Saiz, C. J. Gómez-García, V. Laukhin, A. Pérez-Benítez, C. Rovira, J. Veciana, Adv. Mater. 1997, 9, 984-987.
21. [7g] E. Laukhina, E. Ribera, J. Vidal-Gancedo, S. Khasanov, L. Zorina, R. Shibaeva, E. Canadell, V. Laukhin, M. Honold, M.-S. Nam, J. Singleton, J. Veciana, C. Rovira, Adv. Mater. 2000, 12, 54.
22. K. S. Varma, A. Burry, N. H. Harris, A. E. Underbill, Synthesis 1987, 837.
23. J. Larsen, C. Lenoir, Synthesis 1989, 134.
24. Compound 4 was obtained from 4,5-bis(methoxycarbonyl)-1,3-dithiole-2-thione (3) in high yield (80%) by a conventional method: K. Hartke, T. Kissel, J. Quante, R. Matusch, Chem. Ber. 1980, 112, 1898.
25. B. R. O'Connor, F. N. Jones, J. Org. Chem. 1970, 35, 2002.
26. [12a] N. C. Gonella, M. P. Cava, J. Org. Chem. 1978, 43, 369.
27. [12b] J. M. Fabre, D. Serhani, K. Saoud, S. Chakroune, M. Hoch, Synth. Met. 1993, 60, 295.
28. [12c] I. V. Sudmale, G. V. Tormos, V. Y. Khodorkosky, A. S. Edzina, O. J. Neilands, M. P. Cava, J. Org. Chem. 1993, 58, 1355.
29. [12d] K. Lerstrup, I. Johannsen, M. Jorgensen, Synth. Met. 1988, 27, B9.
30. [12e] M. R. Bryce, A. J. Moore, Symthesis 1991, 26.
31. E. M. Engler, V. V. Patel, J. R. Anderson, R. R. Schumaker, A. A. Fukushima, J. Am. Chem. Soc. 1978, 100, 3769.
32. Because of the low quality of the crystals of ETEDT-TTF, the data quality and subsequent refinement were poor, preventing a detailed and accurate discussion of the crystal packing.
33. [15a] H. Kobayashi, A. Kobayashi, Y. Sasaki, G. Saito, H. Inokuchi, Bull. Chem. Soc. Jpn. 1986, 59, 301.
34. [15b] J. J. Novoa, M. C. Rovira, C. Rovira, J. Veciana, J. Tarrés, Adv. Mater. 1995, 7, 233.
35. K. Saito, Y. Ishikawa, K. Kikuchi, I. Ikemoto, K. Kobayashi, Acta Crystallogr. 1989, C45, 1403-1406.
36. B. Garreau, D. D. Mountauzon, P. Cassoux, J. P. Legros, J.-M. Fabre, K. Saoud, S. Chakroune, New J. Chem. 1995, 19, 161-71.
37. [18a] W. P. Cooper, N. C. Kenny, J. W. Eduards, A. Nagel, F. Wudl, P. Coppens, J. Chem. Soc. D 1971, 16, 889.
38. [18b] W. F. Cooper, J. W. Edwards, F. Wudl, P. Coppens, Cryst. Struct. Commun. 1974, 3, 23.
39. A Ellern, J. Bernstein, J. Y. Becker, S. Zamir, L. Shahal, Chem. Mater. 1994, 6, 1378
40. M.-H. Whangbo, D. Jung, J. Ren, M. Evain, J. J. Novoa, F. Mota, S. Alvarez, J. M. Williams, M. A. Beno, A. M. Kini, H. H. Wang, J. R. Ferraro, in The Physics and Chemistry of Organic Superconductors (Eds.: G. Saito, S. Kagoshima), Springer-Verlag, Berlin, 1990, vol. 51, p. 262.
41. J. B. Torrance, B. A. Scott, B. Weiber, F. B. Kaufmann, P. E. Seiden, Phys. Rev. B 1979, 19, 730.
42. L.-K. Chou, M. A. Quijada, M. B. Clevenger, G. F. Oliveira, K. A. Abboud, D. B. Tanner, D. R. Talham, Chem. Mater. 1995, 7, 530.
43. V. Laukhin, E. Ribera, C. Rovira, J. Veciana, M. Gener, E. Canadell, T. Togonidze, S. Khasanov, R. Shibaeva, W. Biberacher, K. Andres, M. V. Kartsovnik, Synth. Met. 1999, 102, 1772.
44. C. K. Fair, MolEN, An Interactive Intelligent System for Crystal Structure Analysis, Delft, 1990.
45. G. M. Sheldrick, Acta Crystallogr. A 1990, 46, 467.
46. G. M. Sheldrick, University of Göttingen, Göttingen, 1997
47. J. Llacay, I. Mata, E. Molins, J. Veciana, C. Rovira, Adv. Mater. 1998, 3, 330.
48. D. L. Lichtenberger, R. L.; Johnston, K. Hinkelmann, T. Suzuki, F. Wudl, J. Am. Chem. Soc. 1990, 112, 3302.
49. G. Schukat, A. M. Richter, E. Fanghänel, Sulfur Rep. 1987, 7, 155.
50. L. Cavara, F. Gerson, D. O. Cowan, K. Lerstrup, Helv. Chim. Acta 1986, 69, 141.
51. A. Terahara, H. Ohya-Nishiguchi, N. Hirota, H. Awaji, T. Kawase, S. Yoneda, T. Sugimoto, Z. Yoshida, Bull. Chem. Soc. Jpn. 1984, 57, 1760.