Synthesis and electron-donor ability of the first conjugated π-extended tetrathiafulvalene dimers

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4492-4499

  Díaz, Marta C ^a   Illescas, Beatriz M ^a   Seoane, Carlos ^a   Martín, Nazario ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSITIONS; MONOMERS; OLEFINS; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL); VINYL RESINS;

ELECTRON DONORS; OLEFINATION; QUINONE;

DIMERS;

1 (ANTHRAQUINON 2 YL) 2 [9,10 BIS(1,3 DITHIOL 2 YLIDENE) 9,10 DIHYDROANTHRACEN 2 YL]ETHYLENE; 1,2 BIS[9,10 BIS(1,3 DITHIOL 2 YLIDENE) 9,10 DIHYDROANTHRACEN 2 YL]ETHYLENE; 1,2 BIS[9,10 BIS[4,5 BIS(METHYLTHIO) 1,3 DITHIOL 2 YLIDENE] 9,10 DIHYDROANTHRACEN 2 YL]ETHYLENE; 1,2 DI(ANTHRAQUINON 2 YL)ETHYLENE; ANTHRACENE DERIVATIVE; ETHYLENE DERIVATIVE; MONOMER; PHOSPHONIC ACID DERIVATIVE; QUINONE DERIVATIVE; STILBENE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; HORNER REACTION; OLEFINATION; OXIDATION; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 3042701755     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049741z     Document Type: Article

References (57)

1. (a) Bryce, M. R. J. Mater. Chem. 2000, 10, 589.
2. (b) Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372.
3. (a) Bryce, M. R.; Moore, A. J.; Hasan, M.; Ashwell, G. J.; Fraser, A. T.; Clegg, W.; Husthouse, M. B.; Karaulov, A. I. Angew. Chem., Int. Ed. Engl. 1990, 29, 1450.
4. (b) Yamashita, Y.; Kobayashi, Y.; Migashi, T. Angew. Chem., Int. Ed. Engl. 1989, 8, 570.
5. (a) Martín, N.; Pérez, I.; Sánchez, L.; Seoane, C. J. Org. Chem. 1997, 62, 5690.
6. (b) Herranz, M. A.; Martín, N. Org. Lett. 1999, 1, 2005.
7. (c) M. A. Herranz, N. Martín, L. Sánchez, C. Seoane, D. M. Guldi, J. Organomet. Chem. 2000, 2, 599.
8. (d) Martin, N.; Sánchez, L.; Guldi, D. M. Chem Commun. 2000, 113.
9. (e) Herranz, M. A.; Martin, N.; Ramey, J.; Guldi, D. M. Chem. Commun. 2002, 2968.
10. (f) González, S.; Martín, N.; Swartz, A.; Guldi, D. M. Org. Lett. 2003, 5, 557.
11. (g) González, S.; Martín, N.; Guldi, D. M. J. Org Chem. 2003, 68, 779.
12. (a) Herranz, M. A.; Martin, N.; Sánchez, L.; Garin, J.; Orduna, J.; Alcalá, R.; Villacampa, B.; Sánchez, C. Tetrahedron 1998, 54, 11651.
13. (b) Otero, M.; Herranz, M. A.; Seoane, C.; Martín, N.; Garin, J.; Orduna, J.; Alcalá, R.; Villacampa, B. Tetrahedron 2002, 58, 7463.
14. Bryce, M. R.; Batsanov, A. S.; Finn, T.; Hansen, T. K., Howard, J. A. K.; Kamenjicki, M.; Ledner, I. K.; Asher, S. A. Chem. Commun. 2000, 295.
15. Perepichka, D. F.; Bryce, M. R.; Perepichka, I. F.; Lyubchik, S. B.; Christensen, C. A.; Godbert, N.; Batsanov, A. S.; Levillain, E.; McInnes, E. J. L.; Zhao, J. P. J. Am. Chem. Soc. 2002, 124, 14227.
16. Giacalone, F.; Segura, J. L.; Martín, N.; Guldi, D. M. J. Am. Chem. Soc. 2004, 126, 5340-5341.
17. (a) Martín, N.; Sánchez, L.; Seoane, C.; Ortí, E.; Viruela, P. M.; Viruela, R. J. Org. Chem. 1998, 63, 1268.
18. (b) For a recent review on quinonoid exTTFs, see: Martín, N.; Orti, E. In Handbook of Advanced Electronic Photonic Materials and Devices; Nalwa, H. S., Ed.; Academic Press: New York, 2001; Vol. 3, Chapter 6.
19. Díaz, M. C.; Herranz, M. A.; Illescas, B. M.; Martín, N.; Godbert, N.; Bryce, M. R.; Luo, Ch.; Swartz, A.; Anderson, G.; Guldi, D. M. J. Org. Chem. 2003, 68, 7711.
20. (a) Adam, M.; Müllen, K. Adv. Mater. 1994, 6, 439.
21. (b) Jørgensen, T.; Hansen, T. K.; Becher, J. Chem. Soc. Rev. 1994, 41.
22. (c) Otsubo, T.; Aso, Y.; Takimiya, K. Adv. Mater. 1996, 8, 203.
23. (d) Simonsen, K. B.; Becher, J. Synlett 1997, 1211.
24. (e) Roncali, J. J. Mater. Chem. 1997, 7, 2307.
25. (f) Becher, J.; Lau, J.; Mørk, P. In Electronic Materials: The Oligomer Approach; Müllen, K., Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998; p 198.
26. (g) Bryce, M. R.; Davenport, W.; Goldenberg, L. M.; Wang, C. Chem. Commun. 1998, 945.
27. (h) Bryce, M. R. Adv. Mater. 1999, 11, 11.
28. (i) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153.
29. (j) Bryce, M. R. J. Mater. Chem. 2000, 10, 589.
30. (a) Cerrada, E.; Bryce, M. R.; Moore, A. J. J. Chem. Soc., Perkin Trans. 1 1993, 537.
31. (b) Marshallsay, G. J.; Bryce, M. R. J. Org. Chem. 1994, 59, 6847.
32. (c) Boulle, C.; Desmars, O.; Gautier, N.; Hudhomme, P.; Cariou, M.; Gorgues, A. Chem. Commun. 1998, 2197.
33. (d) Gautier, N.; Mercier, N.; Riou, A.; Gorgues, A.; Hudhomme, P. Tetrahedron Lett. 1999, 40, 5997.
34. (e) Supramolecular Engineering of Synthetic Metallic Materials: Conductors amd Magnets; Veciana, J., Rovira, C., Amabilino, D. B., Eds.; NATO ASI Series, Vol. 518; Kluwer: Dordrecht, 1999.
35. (f) Pérez, I.; Liu, S. G.; Martin, N.; Echegoyen, L. J. Org. Chem. 2000, 65, 9092.
36. (g) Gautier, N.; Gallego-Planas, N.; Mercier, N.; Levillain, E.; Hudhomme, P. Org. Lett, 2002, 4, 961.
37. Martín, N.; Pérez, I.; Sánchez, L.; Seoane, C. J. Org. Chem. 1997, 62, 870.
38. Godbert, N.; Bryce, M. R.; Dahaoui, S.; Batsanov, A. S.; Howard, J. A. K.; Hazendok, P. Eur. J. Org. Chem. 2001, 749.
39. Sánchez, L.; Pérez, I.; Martín, N. Guldi, D. M. Chem. Eur. J. 2003, 9, 2457.
40. (a) Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695.
41. (b) Guldi, D. M. Chem. Commun. 2000, 321.
42. (a) Bryce, M. R.; Finn, T.; Moore, A. J. Tetrahedron Lett. 1999, 40, 3271.
43. (b) Christensen, C. A.; Bryce, M. R.; Batsanov, A. S.; Howard, J. A. K.; Jeppesen, J. O.; Becher, J. Chem. Commun. 1999, 2433.
44. (c) Díaz, M. C.; Illescas, B.; Martín, N. Tetrahedron Lett. 2003, 44, 945.
45. House, H. O.; Koepsell, D. G.; Campbell, W. J. J. Org. Chem. 1972, 37, 1003.
46. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
47. (a) Bryce, M. R.; Moore, A. J. Synthesis 1991, 26.
48. (b) Parg, R. P.; Kilburn, J. D.; Ryan, T. G. Synthesis 1994, 195 and references therein.
49. Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
50. Davies, D. G.; Hodge, P.; Yates, P. J. Chem. Soc., Perkin Trans. 1 1973, 850.
51. Moore, A. J.; Bryce, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 157.
52. (a) Guldi, D. M.; Sánchez, L.; Martin, N. J. Phys. Chem. 2001, 105, 7139.
53. (b) Jones, A. E.; Christensen, Ch. A.; Perepichka, D. F.; Batsanov, A. S.; Beeby, A.; Low, P. J.; Bryce, M. R.; Parker, A. W. Chem. Eur. J. 2001, 7, 973.
54. (a) Pérez, I.; Liu, S.-G.; Martín, N.; Echegoyen, L. J. Org. Chem. 2000, 65, 3796.
55. (b) Otsubo, T.; Kochi, Y.; Bitoh, A.; Andura, F. Chem. Lett. 1994, 2047.
56. Green, D. C.; Allen, R. W. J. Chem. Soc., Chem. Commun. 1978, 832.
57. Fernández-Refojo, M.; Pan, Y.-L.; Kun, K. A.; Cassidy, H. G. J. Org. Chem. 1960, 25, 416.