Synthesis and electrochemistry of soluble double-bridged tetrathiafulvalene (TTF)-p-benzoquinone dyads

Tetrahedron

Volumn 54, Issue 12, 1998, Pages 2853-2866

  González, Mar ^a   Illescas, Beatriz ^a   Martín, Nazario ^a   Segura, José L ^a,b   Seoane, Carlos ^a   Hanack, Michael ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; BENZOQUINONE; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; ELECTROCHEMISTRY; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032546202     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83022-6     Document Type: Article

References (44)

1. Metzger, R.M. ; Panetta. Ch. New J. Chem. 1991, 15, 209 and references cited therein. See also : Molecular Electronic-Science and Technology. Aviram A., Ed. ; Engeneering Foundation. New York, 1989.
2. Metzger, R.M. ; Panetta. Ch. New J. Chem. 1991, 15, 209 and references cited therein. See also : Molecular Electronic-Science and Technology. Aviram A., Ed. ; Engeneering Foundation. New York, 1989.
3. a) Boyd, R.W. ; Nonlinear Optics ; Academic Press : New York, 1992.
4. b) Prasad, P.N. ; Williams, D.J. Introduction to Nonlinear Optical Effects in Molecules and Polymers ; Wiley : New York, 1991.
5. c) Long, N.J. Angew. Chem. Int. Ed Engl. 1995, 34, 21.
6. d) Wong, M,S. ; Bosshard, Ch. ; Pan, F. ; Günter, P. Adv. Mater. 1996, 8, 677 .
7. e) Dalton, I.R ; Harper, A.W, ; Ghosn, R. ; Steier, W.H. ; Ziari, M. ; Fettermen, H. ; Shi, Y. ; Mustacich, R.V. ; Jen, A.K.-Y. ; Shea, K.J. Chem. Mater. 1995, 7, 1060.
8. a) Photoinduced Electron Transfer; Fox, M.A. ; Chanon, M. Eds., Elsevier : Amsterdam, 1988 and references cited therein.
9. b) Danielson, E. ; Elliot, C.M. ; Merket, J.N. ; Meyer, T.J. J. Am. Chem. Soc. 1987, 109, 2519
10. c) Wasielewski, M.R. ; Niemczyk, M.P.; Svek, W.A. ; Pewitt, E.B, J. Am. Chem. Soc. 1985, 107, 5562
11. d) Brédas, J.L. ; Adant, C. ; Tackx, P. ; Persoons, A. Chem. Rev. 1994, 94, 243.
12. a) Bando, P. ; Davidkov, K. ; Martin, N. ; Segura, J.L. ; Seoane, C. ; González, A. ; Pingjurón, J.M. Synth. Met. 1993, 56, 1721
13. b) Bando, P. ; Martín, N. ; Segura, J.L. ; Seoane, C. ; Ortí, E. ; Viraela. P.M. ; Viniela, R, ; Albert, A. ; Cano, F.H. J. Org. Chem. 1994, 59, 4618
14. c) Illescas, B. ; Martin, N. ; Segura, J.L. ; Seoane, C. ; Ortí, E. ; Viruela, P.M. ; Viniela, R. J. Mater. Chem. 1995, 5, 1563
15. d) Martin, N. ; Segura, J.L. ; Seoane, C. ; Orti, E. ; Viruela, P.M. ; Viruela, R. ; Albert, A. ; Cano, F.H. ; Vidal-Gancedo, J. ; Rovira, C. ; Veciana, J. J. Org. Chem. 1996, 61, 3041.
16. Segura, J.L. ; Martin, N. ; Seoane, C. ; Hanack, M. Tetrahedron Lett. 1996, 37, 2503.
17. a) Narita, M. ; Pittman, C.U. Synthesis 1976, 489.
18. b) Schukat, G. ; Richter, A.M. ; Fanghänel, E. Sulphur Rep. 1987, 7, 155 .
19. c) Schukat, G. , Fanghänel, E. Sulphur Rep. 1993, 14, 245 .
20. d) Jørgensen, T. ; Hanse, T.K. ; Becher, J. Chem. Soc. Rev. 1994, 23, 41
21. e) Adam ; M., Müllen, K. Adv. Mater. 1994. 6, 439 .
22. e) Bryce, M.R. J. Mater. Chem. 1995, 5, 1481 .
23. f) Garín, J. Adv. Heterocycl. Chem. 1995, 62, 249.
24. Molecular Electronics in Granular Nanoelectronics, Ferry, O.K. Ed. Plenum Press, New York, 1991.
25. Avirarm, A. ; Ratner, MA. Chem. Phys. Lett., 1974, 29, 277.
26. a) Metzger, R.M, Panetta, Ch. J. Molec. Electr., 1989, 5, 1.
27. b) Panetta, Ch. ; Heimer, N.E. ; Hussey, C.L. ; Metzger, R.M. Synlett, 1991, 301.
28. Metzger, R.M. ; Chen, B. ; Höpfner, U. ; Lakshmikantham, M.V. ; Villlaume, D. ; Kawai, T. ; Wu, X. ; Tachibana, H. ; Hughes, T.V. ; Sakurai, H. ; Baldwin, J.W ; Hosch, C. ; Cava. M.P. ; Brehmer, L. ; Ashwell, G.J. J. Am. Chem. Soc., in press, to appear Dec, 1997.
29. For a recent review on electron acceptors see: Martin, N. ; Segura, J.L. ; Seoane, C. J. Mater. Chem., 1997, 7, 1661.
30. Röhrichn J. ; Müllen, K. J. Org. Chem., 1992, 57, 2374.
31. Steinmecke, G. ; Sieler, H.-J. ; Kirmse, R, ; Hoyer, E. Phosphorus Sulfur, 1979, 7, 49.
32. Jacob, P. ; Callery, P.S. ; Shulgin, A.T. ; Castagnoli, N. J. Org. Chem, 1976, 41, 3627.
33. Snyder, C.D. ; Rappoport, H. J. Am. Chem. Soc., 1972, 94, 227.
34. Errauriz, B. ; Tapia, R. ; Valderrama, J.A., Tetrahedron Lett., 1985, 26, 819.
35. Hellberg, J. ; Moge, M. ; Schmitt, H. ; von Schütz, J.-U. J. Mater. Chem., 1995, 5, 1549.
36. Gemmell, C. ; Kilbum, J.D. ; Ueck, H. ; Underbill, A.E. Tetrahedron Lett., 1992, 33, 3923.
37. Gemmell, C. ; Janeiro, G.C. ; Kilburn, J.D. ; Ueck ; H. ; Underhill, A.E. J. Chem. Soc. Perkin Trans. I, 1994, 2715.
38. Charlton, A. ; Hill, C.A.S. ; Underhill, A.E. ; Malik, K.M.A. ; Hursthouse, M.B. ; Kraulov, A.I. ; Moller, J. J. Mater. Chem., 1994, 4, 1861.
39. Watson ;W.H, Eduok ; E.E., Kashyap ; R.P., Krawiec ; M. Tetrahedron, 1993, 49, 3035.
40. Ikeda, K. ; Kawabata, K. ;Taaeka, K. ; Mizutani, M. Synth. Met., 1993, 49, 3035.
41. Frenzel, S. ; Müllen, K. Synth. Met., 1996, 80, 175.
42. De Angelis ; T.P., Heineman, W.R. J. Chem. Ed, 1979, 53, 529.
43. Salbeck, J. Anal. Chem., 1993, 65, 2169.
44. Frenzel, S. ; Müllen, K. Synth. Met., 1996, 80, 175.