Electron transfer through molecular bridges between reducible pentakis(thiophenyl)benzene subunits

Chemistry - A European Journal

Volumn 7, Issue 6, 2001, Pages 1266-1272

  Mayor, Marcel ^a   Büschel, Michael ^c   Fromm, Katharina M ^d   Lehn, Jean Marie ^a,b   Daub, Jörg ^c  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b UNIVERSITÉ LOUIS PASTEUR   (France)

^c UNIVERSITY OF REGENSBURG   (Germany)

^d Sciences II   (Switzerland)

Author keywords

Conjugation; Electron transfer; Mixed valent compounds; Molecular wires; Polythiobenzenes

Indexed keywords

BENZENE; BRIDGES;

MOLECULAR BRIDGES;

ELECTRONS;

1,4 BIS(PENTATHIOPHENYL)PHENYL BUTA 1,3 DIYNE; 1,4 BIS[[2' (2'',3'',4'',5'',6'' PENTATHIOPHENYL)PHENYL]ETHENYL]BENZENE; BENZALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; DECATHIOPHENYLBENZALDEHYDE AZINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTRON TRANSPORT; SYNTHESIS;

EID: 0035896259     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010316)7:6<1266::AID-CHEM1266>3.0.CO;2-S     Document Type: Article

References (40)

1. J. M. Tour, Chem. Rev. 1996, 96, 573-553, and references therein.
2. M. D. Ward, Chem. Soc. Rev. 1995, 121-134, and references therein.
3. M. A. Ratner, B. Davis, M. Kemp, V. Mujica, A. Roitberg, S. Yaliraki in Molecular Electronics: Science and Technology; Annals of the New York Academy of Science, (Eds.: A. Aviram, M. Ratner), 1998, pp. 22-37.
4. A. Harriman, R. Ziessel, Chem. Commun. 1996, 1707-1716.
5. P. F. H. Schwab, M. D. Levin, J. Michl, Chem. Rev. 1999, 99, 1863-1933, and references therein.
6. F. Barigeletti, L. Flamigni, J.-P. Collin, J.-P. Sauvage, Chem. Commun. 1997, 333-338.
7. J.-M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995, Chapter 8.
8. Molecular Electronics (Eds.: J. Jortner, M. Ratner), Blackwell, Oxford, 1997.
9. E. G. Emberly, G. Kirczenow in Molecular Electronics: Science and Technology; Annals of the New York Academy of Science (Eds.: A. Aviram, M. Ratner), 1998, pp. 54-67.
10. M. Robin, P. Day, Adv. Inorg. Radiochem. 1967, 10, 247-422.
11. T. S. Arrhenius, M. Blanchard-Desce, M. Dvolaitzky, J.-M. Lehn, J. Malthête, Proc. Natl. Acad. Sci. USA 1986, 83, 5355-5359;
12. L. B. Å. Johansson, M. Blanchard-Desce, M. Almgren, J.-M. Lehn, J. Phys. Chem. 1989, 93, 6751-6754;
13. S. I. Kugimiya, T. Lazrak, M. Blanchard-Desce, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1991, 1179-1182.
14. A. Knorr, J. Daub, Angew. Chem. 1997, 109, 2926-2929;
15. Angew. Chem. Int. Ed. Engl. 1997, 36, 2817-2819.
16. "Sulfur-Containing Oligomers", P. Bäuerle in Electronic Materials: The Oligomer Approach (Eds. K. Müllen, G. Wegner), VCH, Weinheim, 1998, Chapter 2.
17. Examples include: S. F. Nelsen, H. Q. Tran, M. A. Nagy, J. Am. Chem. Soc. 1998, 120, 298-304;
18. C. Lambert, G. Nöll, Angew. Chem. 1998, 110, 2239-2242;
19. Angew. Chem. Int. Ed. 1998, 37, 2107-2110;
20. J. Bonvoisin, J.-P. Launay, M. Van der Auweraer, F. C. de Schryver, J. Phys. Chem. 1994, 98, 5052-5057.
21. A. F. Diaz, K. K. Kanazawa, J. P. Gardini, J. Chem. Soc. Chem. Commun. 1979, 635.
22. Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. D. Davis, D. D. MacNicol, F. Vögtle, G. A. Downing, J.-M. Lehn), Elsevier, Oxford, 1996, pp. 421-464.
23. J. H. R. Tucker, M. Gingras, H. Brand, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1997, 1303-1307.
24. M. Mayor, J.-M. Lehn, Helv. Chim. Acta 1997, 80, 2277-2285.
25. M. Mayor, J.-M. Lehn, K. M. Fromm, D. Fenske, Angew. Chem. 1997, 109, 2468-2471;
26. Angew. Chem. Int. Ed. Engl. 1997, 36, 2370-2372.
27. M. Mayor, J.-M. Lehn, J. Am. Chem. Soc. 1999, 121, 11231-11232.
28. 2 with the SHELX-97 package. All heavy atoms were refined anisotropically. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-147302. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223336-033; e-mail: deposit@ccdc.cam. ac.uk)..
29. E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 36, 3769-3772.
30. A. S. Hay, J. Org. Chem. 1960, 25, 1275.
31. C. Creutz, Prog. Inorg. Chem. 1983, 30, 1-71.
32. M. Büschel, C. Stadler, C. Lambert, M. Beck, J. Daub, J. Electroanal. Chem. 2000, 484, 24-32, and references therein.
33. B. Soucaze-Guillous, H. Lund, J. Electroanal. Chem. 1997, 423, 109-114.
34. Assuming that the adiabatic energy surface for thermal electron transfer (ET) is obtained from a two-state classical model between diabatic surfaces; see: N. S. Hush, Prog. Inorg. Chem. 1967, 8, 391-444;
35. N. S. Hush, Electrochim. Acta 1968, 13, 1005-1023;
36. N. S. Hush, Coord. Chem. Rev. 1985, 64, 135-157.
37. S. F. Nelsen, Chem. Eur. J. 2000, 6, 581-588, and references therein.
38. A. D. U. Hardy, D. D. MacNicol, D. R. Wilson, J. Chem. Soc. Perkin Trans. 2 1979, 1011-1019.
39. F. Diederich in Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, 1995, 443-471.
40. U. H. F. Bunz, Y. Rubin, Y. Tobe, Chem. Soc. Rev. 1999, 28, 107-119.