A new type of π-electron donors with one dithiole unit: Substituted 7- (1,3-dithiol-2-ylidene)-7-hydrobenz[d,e]anthracenes

European Journal of Organic Chemistry

Volumn , Issue 5, 1999, Pages 1239-1247

  Martín, Nazario ^a   Ortí, Enrique ^b   Sánchez, Luis ^a   Viruela, Pedro M ^b   Viruela, Rafael ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Ab initio calculations; Charge transfer complexes; Cyclic voltammetry; Density functional calculations; Electron donors

Indexed keywords

ANTHRACENE DERIVATIVE;

ARTICLE; ELECTRIC CONDUCTIVITY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; POTENTIOMETRY; PREDICTION; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS; VALIDATION PROCESS;

EID: 0032783371     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199905)1999:5<1239::AID-EJOC1239>3.0.CO;2-R     Document Type: Article

References (73)

1. [1a] For recent reviews, see: J. Becher, J. Lau, P. Mørk in Electronic Materials: The Oligomer Approach (Eds.: K. Müllen, G. Wegner), Wiley-VCH, New York, 1998, chapter 2, p. 198; T. Otsubo, Y. Aso, K. Takiyima, Adv. Mater. 1996, 8, 203-211.
2. [1a] For recent reviews, see: J. Becher, J. Lau, P. Mørk in Electronic Materials: The Oligomer Approach (Eds.: K. Müllen, G. Wegner), Wiley-VCH, New York, 1998, chapter 2, p. 198; T. Otsubo, Y. Aso, K. Takiyima, Adv. Mater. 1996, 8, 203-211.
3. [1b] See also: V. Khodorkovsky, J. V. Becker, in Organic Conductors: Fundamental and Applications (Ed.: J. P. Farges), Marcel Dekker, New York, 1994, chapter 3, p. 75. -
4. For more recent articles, see: [1c] J. Lau, P. Blanchard, A. Riou, M. Jubault, M. P. Cava, J. Becher, J. Org. Chem. 1997, 62, 4936-4942.
5. [1d] I. Sudmale, A. Puplovskis, A. Edzina, O. Neilands, V. Khodorkovsky. Synthesis 1997, 750-752.
6. [1e] M. J. Cook, G. Cooke, A. Jafari-Fini, J. Chem. Soc., Chem. Commun. 1996, 1925-1926.
7. [1f] M. R. Bryce, Adv. Mater. 1999, 11, 11-23.
8. [2a] M. R. Bryce, W. Devonport, L. M. Goldenberg, C. Wang, J. Chem. Soc., Chem. Commun. 1998, 945-951.
9. [2b] C. A. Christensen, L. M. Goldenberg, M. R. Bryce, J. Becher, J. Chem. Soc., Chem. Commun. 1998, 509-510.
10. [2c] W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore, L. M. Goldenberg, J. Mater. Chem. 1998, 8, 1361-1372.
11. [2d] C. Wang, M. R. Bryce, A. Batsanov, C. F. Stanley, A. Beeby, J. A. K. Howard, J. Chem. Soc., Perkin Trans. 2 1997, 1671-1678.
12. [2e] C. Wang, M. R. Bryce, A. Batsanov, L. M. Goldemberg, J. A. K. Howard, J. Mater. Chem. 1997, 7, 1189-1199.
13. [2f] P. Blanchard, N. Svenstrup, J. Becher, J. Chem. Soc., Chem. Commun. 1996, 615-616.
14. [2h] M. Adam, E. Müllen, Adv. Mater. 1994, 6, 439-459.
15. [2h] M. Adam, E. Fanghänel, K. Müllen, Y.-J. Shen, R. Wegner, Synth. Met. 1994, 66, 275-283.
16. [2i] M. R. Bryce, W. Devonport, A. J. Moore, Angew, Chem. 1994, 106, 1862-1864; Angew. Chem. Int. Ed. Engl. 1994, 33, 1761-1763.
17. [2i] M. R. Bryce, W. Devonport, A. J. Moore, Angew, Chem. 1994, 106, 1862-1864; Angew. Chem. Int. Ed. Engl. 1994, 33, 1761-1763.
18. [2j] M. R. Bryce, G. J. Marshallsay, A. J. Moore, J. Org. Chem. 1992, 57, 4859-4862.
19. [2k] M. Jørgensen, K. A. Lerstrup, K. Bechgaard, J. Org. Chem. 1991, 56, 5684-5688.
20. For a recent review, see: J. Roncali, J. Mater. Chem. 1997, 7, 2307-2321. See also:
21. [3a] H. Brisset, S. Le Moustarder, P. Blanchard, B. Illien, A. Riou, J. Orduna, J. Garín, J. Roncali, J. Mater. Chem. 1997, 7, 2027-2033.
22. [3b] M. R. Bryce, J. Mater. Chem. 1995, 5, 1481-1496.
23. [3c] H. Brisset, C. Thobie-Gautier, M. Jubault, A. Gorgues, J. Roncali, J. Chem. Soc., Chem. Commun. 1994, 1765.
24. [3d] A. K. Jen, V. P. Rao, K. J. Drost, K. Y. Wong, M. P. Cava, J. Chem. Soc., Chem. Commun. 1994, 2057-2058.
25. [3e] K. Takahashi, T. Nihira, K. Tomitani, J. Chem. Soc., Chem. Commun. 1993, 1617-1619.
26. [3f] T. K. Hansen, M. V. Lakshmikantham, M. P. Cava, R. E. Niziurski-Man, F. Jensen, J. Becher, J. Am. Chem. Soc. 1992, 114, 5035-5039.
27. [3g] A. S. Benhamed-Gasmi, P. Frère, B. Garrigues, A. Gorgues, M. Jubault, R. Carlier, F. Texier, Tetrahedron Lett. 1992, 33, 6457-6460.
28. [3h] T. K. Hansen, M. V. Lakshmikantham, M. P. Cava, R. M. Metzger, J. Becher, J. Org. Chem. 1991, 56, 2720-2722.
29. [3i] A. J. Moore, M. R. Bryce, D. Ando, M. B. Hursthouse, J. Chem. Soc., Chem. Commun. 1991, 320-321.
30. [3j] K. Takahashi, K. Tomitani, J. Chem. Soc., Chem. Commun. 1991, 821.
31. [3k] A. J. Moore, M. R. Bryce, J. Chem. Soc., Perkin Trans. 1 1991, 157-168.
32. [3l] M. R. Bryce, A. J. Moore, M. Hasan, G. J. Ashwell, A. T. Fraser, W. Clegg, M. B. Hursthouse, A. I. Karaulov, Angew. Chem. 1990, 102, 1493-1496; Angew. Chem. Int. Ed. Engl. 1990, 29, 1450-1453.
33. [3l] M. R. Bryce, A. J. Moore, M. Hasan, G. J. Ashwell, A. T. Fraser, W. Clegg, M. B. Hursthouse, A. I. Karaulov, Angew. Chem. 1990, 102, 1493-1496; Angew. Chem. Int. Ed. Engl. 1990, 29, 1450-1453.
34. [3m] V. Y. Khodorkovsky, L. N. Veselova, O. Y. Neilands, Khim. Geterotsikl. Soedin. 1990, 130; Chem. Abstr. 1990, 113, 22868t.
35. [3m] V. Y. Khodorkovsky, L. N. Veselova, O. Y. Neilands, Khim. Geterotsikl. Soedin. 1990, 130; Chem. Abstr. 1990, 113, 22868t.
36. [3n] H. Awaji, T. Sugimoto, Y. Misaki, T. Kawase, S. Yoneda, Z. Yoshida, Chem. Mater. 1989, 1, 535-539.
37. [3o] Y. Yamashita, Y. Kobayashi, T. Miyashi, Angew. Chem. 1989, 101, 941-942; Angew. Chem. Int. Ed. Engl. 1989, 28, 1052-1053.
38. [3o] Y. Yamashita, Y. Kobayashi, T. Miyashi, Angew. Chem. 1989, 101, 941-942; Angew. Chem. Int. Ed. Engl. 1989, 28, 1052-1053.
39. [3p] Z. Yoshida, T. Kawase, H. Awaji, I. Sugimoto, T. Sugimoto, S. Yoneda, Tetrahedron Lett. 1983, 24, 3469-3472.
40. T. Suzuki, T. Sakimura, S. Tanaka, Y. Yamashita, H. Shiohara, T. Miyashi, J. Chem. Soc., Chem. Commun. 1994, 1431-1432.
41. M. Kozaki, S. Tanaka, Y. Yamashita, J. Org. Chem. 1994, 59, 442-450.
42. [6a] A. S. Benhamed-Gasmi, P. Frère, J. Roncali, E. Elandaloussi, J. Orduna, J. Garín, M. Jubalult, A. Gorgues, Tetrahedron Lett. 1995, 36, 2983-2986.
43. [6b] P. Hascoat, D. Lorcy, A. Robert, R. Carlier, A. Tallec, K. Boubekeur, P. Batail, J. Org. Chem. 1997, 62, 6086-6089.
44. [6c] P. Hapiot, D. Lorcy, A. Tallec, R. Carlier, A. Robert, J. Phys. Chem. 1996, 100, 14823-14827.
45. [6d] D. Lorcy, R. Carlier, A. Robert, A. Tallec, P. Le Maguerès, L. Ouahab, J. Org. Chem. 1995, 60, 2443-2447.
46. [6e] A. Ohta, Y. Yamashita, J. Chem. Soc., Chem. Commun. 1995, 1761-1762.
47. [6f] U. Schöberl, J. Salbeck, J. Daub, Adv. Mater. 1992, 4, 41-44.
48. [6g] K. Mayer, H. Kröber, J. Prakt. Chem. 1974, 316, 907.
49. [6i] W. Kirmse, L. Horner, Justus Liebigs Ann. Chem. 1958, 614, 4-12.
50. C. Kroenke, V. Enkelmann, G. Wegner, Angew. Chem. 1980, 92, 941-948; Angew. Chem. Int. Ed. Engl. 1980, 19, 912-919.
51. C. Kroenke, V. Enkelmann, G. Wegner, Angew. Chem. 1980, 92, 941-948; Angew. Chem. Int. Ed. Engl. 1980, 19, 912-919.
52. [8a] N. Martín, L. Sánchez, C. Seoane, E. Ortí, P. M. Viruela, R. Viruela, J. Org. Chem. 1998, 63, 1268-1279.
53. [8b] N. Martin, L. Sánchez, C. Seoane, C. Fernández, Synth. Met. 1996, 78, 137-141.
54. N. Martín, I. Pérez, L. Sánchez, C. Seoane, J. Org. Chem. 1997, 62, 870-877.
55. [10a] R. P. Parg, J.-D. Kilburn, T. G. Ryan, Synthesis 1994, 195-198, and references cited therein.
56. [10b] M. R. Bryce, A. J. Moore, Synthesis 1991, 26-28.
57. [11a] K. Sukumar, A. Bury, N. Harris, A. Underhill, Synthesis 1987, 837-838.
58. [11b] G. Steimecke, H. Sieler, R. Kirmse, E. Hoyer, Phosphorus Sulfur 1979, 7, 49-58.
59. The synthesis and electrochemistry of the parent unsubstituted compound 11a have been reported previously [8b].
60. K. Lahlil, A. Moradpour, C. Bowlas, F. Menou, P. Cassoux, J. Bonvoisin, J. P. Launay, G. Dive, D. Dehareg, J. Am. Chem. Soc. 1995, 117, 9995-10002.
61. J. S. Miller, D.A. Dixon, Science 1987, 235, 871.
62. J. S. Chappell, A. N. Bloch, W. A. Bryden, M. Maxfiled, P. O. Poehler, D. O. Cowan, J. Am. Chem. Soc. 1981, 103, 2442-2443.
63. R. C. Rowland, R. Taylor, J. Phys. Chem. 1996, 100, 7384-7391.
64. M. R. Bryce, M. A. Coffin, M. B. Hursthouse, A. I. Karaulov, K. Müllen, H. Scheich, Tetrahedron Lett. 1991, 32, 6029-6032.
65. [18a] E. Demiralp, W. A. Goddard, J. Phys. Chem. A 1997, 101, 8128-8131.
66. [18b] R. Liu, X. Zhou, H. Kasmai, Spectrochim. Acta A 1997, 53, 1241-1256.
67. [18c] P. M. Viruela, R. Viruela, E. Orti, to be published.
68. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian 94, Revision B.1, Gaussian Inc., Pittsburgh PA, 1995.
69. The B3P86 functional consists of Becke's three-parameter hybrid functional,[20a] which is a hybrid of Hartree-Fock exchange with local and gradient-corrected exchange and correlation terms, with the non-local correlation provided by the "Perdew 86"[20b] expression.
70. [20a] A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
71. [20b] J. P. Perdew, Phys. Rev. B 1986, 33, 8822-8824.
72. P. C. Hariharan, J. A. Pople, Chem. Phys. Lett. 1972, 16, 217-219.
73. H. B. Schlegel, J. Comput. Chem. 1982, 3, 214-218.