Intramolecular electron transfer between terminal 1,4-dimethoxybenzene units in radical cations with a [2.2](1,4)naphthalenophane, [2.2](1,4)anthracenophane, and pentacene skeleton

European Journal of Organic Chemistry

Volumn , Issue 6, 1998, Pages 1161-1170

  Wartini, Alexander R ^a   Staab, Heinz A ^a   Neugebauer, Franz A ^a  

^a MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

Author keywords

Cyclic voltammetry; ESR ENDOR spectroscopy; Intramolecular electron transfer; Pentacene; Radical cations; 2.2 (1,4)Anthracenophane; 2.2 (1,4)Naphthalenophanes

Indexed keywords

EID: 0002496070     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199806)1998:6<1161::AID-EJOC1161>3.0.CO;2-1     Document Type: Article

References (37)

1. B. Becker, A. Bohnen, M. Ehrenfreund, W. Wohlfahrt, Y. Sakata, W. Huber, K. Müllen, J. Am. Chem. Soc. 1991, 113, 1121-1127, and references therein.
2. H. Hope, J. Bernstein, K. N. Trueblood, Acta Crystallogr., Sect. B 1972, 28, 1733-1743.
3. F. Gerson, W. B. Martin, Jr., J. Am. Chem. Soc. 1969, 91, 1883-1891.
4. F. Gerson, W. B. Martin, Jr., C. Wydler, J. Am. Chem. Soc. 1976, 98, 1318-1320.
5. J. Bruhin, F. Gerson, W. B. Martin, Jr., C. Wydler, Helv. Chim. Acta 1977, 60, 1915-1923.
6. V. Harnacher, M. Plato, K. Möbius, Chem. Phys. Lett. 1986, 125, 69-73.
7. F. Nemeto, K. Ishizu, T. Toyoda, Y. Sakata, S. Misumi, J. Am. Chem. Soc. 1980, 102, 654-656.
8. A. R. Wartini, J. Valenzuela, H. A. Staab, F. A. Neugebauer, Eur. J. Org. Chem. 1998, 139-148.
9. S. F. Rak, L. L. Miller, J. Am. Chem. Soc. 1992, 114, 1388-1394.
10. A. R. Wartini, J. Valenzuela, H. A. Staab, F. A. Neugebauer. Eur. J. Org. Chem. 1998, 211-227.
11. B. König, B. Knieriem, K. Rauch, A. de Meijere, Chem. Ber. 1993,126, 2531-2534.
12. B. Konig, B. Knieriem, A. de Meijere, Chem. Ber. 1993, 126, 1643-1650.
13. L. Lepage, Y. Lepage, Synthesis 1983, 1018-1019.
14. K. Jung, J. Koreeda, J. Org. Chem. 1989, 54, 5667-5675.
15. J. E. Almlof, M. W. Feyereisen, T. H. Jozefiak, L. L. Miller, J. Am. Chem. Soc. 1990, 112, 1206-1214.
16. E. Clar, F. John, Ber. Dtsch. Chem. Ges. 1929, 62, 3021-3029.
17. D. B. Bruce, R. H. Thomson, J. Chem. Soc. 1952, 2759-2766.
18. Cf.: Y. Lepage, Ann. Clin. (Paris) 1959, 13, 1137-1181.
19. C. Krieger, A. R. Wartini, F. A. Neugebauer, Acta Crystallogr., Sect. C, in press.
20. H. A. Staab, C. P. Herz, Angew. Chem. 1977, 89, 406-407; Angew. Chem. Int. Ed. Engl. 1977, 16, 392-393.
21. H. A. Staab, C. P. Herz, Angew. Chem. 1977, 89, 406-407; Angew. Chem. Int. Ed. Engl. 1977, 16, 392-393.
22. H. Kurreck, B. Kirste, W. Lubitz, Angew. Chem. 1984, 96, 171-193; Angew. Chem. Int. Ed. Engl. 1984, 23, 173-195, and references given therein.
23. H. Kurreck, B. Kirste, W. Lubitz, Angew. Chem. 1984, 96, 171-193; Angew. Chem. Int. Ed. Engl. 1984, 23, 173-195, and references given therein.
24. P. D. Sullivan, J. Phys. Chem. 1970, 74, 2563-2569.
25. A. V. Fratini, M. L. Chabinyc, T. J. Perko, W. W. Adams, Acta Crystallogr. 1995, C51, 904-908.
26. R. Gleiter, K. Staub, H. Irngartinger, T. Oeser, J. Org. Chem. 1997, 62, 7644-7649.
27. [8].
28. A. Carrington, F. Dravnieks, M. C. R. Symons, J. Chem. Soc. 1959, 947-952.
29. A. C. Buchanan, R. Livingston, A. S. Dworkin, C. P. Smith, J. Phys Chem. 1980, 84, 423-427.
30. J. A. Valenzuela, A. J. Bard, J. Phys. Chem. 1969, 73, 779-788.
31. J. R. Bolton, A. Carrington, A. D. McLachlan, Mol. Phvs. 1965, 5, 31-41.
32. H. M. McConnell, J. Chem. Phys. 1956, 24, 632, 764-766; E. T. Strom, G. R. Underwood, D. Jurkowitz, Mol. Phys. 1972, 24, 901-904.
33. H. M. McConnell, J. Chem. Phys. 1956, 24, 632, 764-766; E. T. Strom, G. R. Underwood, D. Jurkowitz, Mol. Phys. 1972, 24, 901-904.
34. A. D. McLachlan, Mol. Phys. 1960, 3, 233-252.
35. J. R. Bolton, J. Chem. Phys. 1967, 46, 408-409.
36. M. Azadi-Ardakani, T. W. Wallace, Tetrahedron 1988, 44, 5939-5952.
37. Y. Tanoue, K. Sakata, M. Hashimoto, S. Morishita, M. Hamada, N. Kai, T. Nagai, Bull. Chem. Soc. Jpn. 1994, 67, 2593-2595.