Synthesis and electrochemical properties of tetrasubstituted tetraphenylethenes

European Journal of Organic Chemistry

Volumn , Issue 15, 2006, Pages 3395-3404

  Schreivogel, Alina ^a   Maurer, Jörg ^a   Winter, Rainer ^a,b   Baro, Angelika ^a   Laschat, Sabine ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Cyclic voltammetry; McMurry reaction; Spectroelectrochemistry; Tetraphenylethenes

Indexed keywords

EID: 33746571472     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600123     Document Type: Article

References (59)

1. Review: F. B. Mallory, C. W. Mallory, Org. React. 1984, 30, 1-456.
2. a) D. Kuck, A. Schuster, R. A. Krause, J. Tellenbroecker, C. P. Exner, M. Penk, H. Boegge, A. Müller, Tetrahedron 2001, 57, 3587-3614;
3. b) R. Oliveira, P. San Martin, E. Dominguez, J. Org. Chem. 2000, 65, 7010-7019;
4. c) J. Nagy, Z. Madarasz, R. Rapp, A. Szoelloesy, J. Nyitrai, D. Döpp, J. Prakt. Chem. 2000, 342, 281-290;
5. d) L. Eshdat, A. Ayalon, R. Beust, R. Shenhar, M. Rabinovitz, J. Am. Chem. Soc. 2000, 122, 12637-12645;
6. e) J. Tellenbroecker, D. Kuck, Angew. Chem. 1999, 111, 1000-1004;
7. Angew. Chem. Int. Ed. 1999, 38, 919-922;
8. f) T. Ogino, F. Wada, T. Murayama, S. Aoki, K. Ohshima, Tetrahedron Lett. 1996, 37, 7065-7068;
9. g) A. Couture, E. Deniau, P. Grandclaudon, C. Simion, Synthesis 1996, 986-990;
10. h) C. Niu, T. Petterson, M. J. Miller, J. Org. Chem. 1996, 61, 1014-1022;
11. i) T. Sato, S. Shimada, K. Hata, Bull. Chem. Soc. Jpn. 1971, 44, 2484-2490;
12. j) T. Sato, S. Shimada, K. Hata, Bull. Chem. Soc. Jpn. 1969, 42, 766-772;
13. k) T. Sato, Y. Goto, K. Hata, Bull. Chem. Soc. Jpn. 1967, 40, 1994;
14. l) N. Kharasch, T. G. Alston, H. B. Lewis, W. Wolf, Chem. Commun. (London) 1965, 242-243;
15. m) F. B. Mallory, C. S. Wood, J. T. Gordon, J. Am. Chem. Soc. 1964, 86, 3094-3102;
16. n) F. B. Mallory, C. S. Wood, J. T. Gordon, L. C. Lindquist, M. L. Savitz, J. Am. Chem. Soc. 1962, 84, 4361-4362;
17. o) R. E. Buckles, J. Am. Chem. Soc. 1955, 77, 1040-1041;
18. p) C. O. Parker, P. E. Spoerri, Nature 1950, 166, 603.
19. a) C. E. Bunker, N. B. Hamilton, Y.-P. Sun, Anal. Chem. 1993, 65, 3460-3465;
20. b) M. L. Mussons, C. Raposo, J. Anaya, M. Grande, J. R. Moran, C. Caballero, J. Chem. Soc., Perkin Trans. 1 1992, 3125-3127;
21. c) B. König, A. de Meijere, Chem. Ber. 1992, 125, 1895-1898;
22. d) H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431-2434;
23. e) R. H. Mitchell, L. Mazuch, B. Shell, P. R. West, Can. J. Chem. 1978, 56, 1246-1252;
24. f) M. V. Sargent, C. J. Timmons, J. Chem. Soc. 1964, 5544-5552.
25. A. Schultz, S. Laschat, S. Diele, M. Nimtz, Eur. J. Org. Chem. 2003, 2829-2839.
26. R. Rathore, S. V. Lindeman, A. S. Kumar, J. K. Kochi, J. Am. Chem. Soc. 1998, 120, 6931-6939.
27. a) W. J. Leigh, D. R. Arnold, Can. J. Chem. 1981, 59, 3061-3075;
28. b) V. D. Parker, K. Nyberg, L. Eberson, J. Electroanal. Chem. Interfacial Electrochem. 1969, 22, 150-152.
29. F. Barbosa, V. Peron, G. Gescheidt, A. Fürstner, J. Org. Chem. 1998, 63, 8806-8814.
30. H. Bock, K. Ruppert, D. Fenske, Angew. Chem. 1989, 101, 1717-1719;
31. Angew. Chem. Int. Ed. Engl. 1989, 28, 1685-1688.
32. a) H. Bock, C. Näther, Z. Havlas, J. Chem. Soc., Chem. Commun. 1995, 1111-1112;
33. b) T. Suzuki, H. Shiohara, M. Monobe, T. Sakimura, S. Tanaka, Y Yamashita, T. Miyashi, Angew. Chem. 1992, 104, 454-456;
34. Angew. Chem. Int. Ed. Engl. 1992, 31, 455-458;
35. c) N. C. Baenziger, R. E. Buckles, T. D. Simpson, J. Am. Chem. Soc. 1967, 89, 3405-3408.
36. S. Sengupta, Synlett 2004, 1191-1194.
37. A. Schultz, S. Diele, S. Laschat, M. Nimtz, Adv. Funct. Mater. 2001, 11, 441-446.
38. J. L. Muzyka, M. A. Fox, J. Org. Chem. 1991, 56, 4549-4552.
39. W. J. Leigh, D. R. Arnold, Can. J. Chem. 1981, 59, 609-620.
40. S. Hünig, M. Kemmer, H. Wenner, I. F. Perepichka, P. Bäuerle, A. Emge, G. Gescheid, Chem. Eur. J. 1999, 5, 1969-1973.
41. S. Hünig, M. Kemmer, H. Wenner, F. Barbosa, G. Gescheidt, I. F. Perepichka, P. Bäuerle, K. Peters, Chem. Eur. J. 2000, 6, 2618-2632.
42. M. J. Plater, T. Jackson, Tetrahedron 2003, 59, 4673-4685.
43. M. O. Wolf, H.H. Fox, M. A. Fox, J. Org. Chem. 1996, 61, 287-294.
44. For redox properties of crownophanes derived from tetraphenylethene see: F. Barbosa, V. Peron, G. Gescheidt, A. Fürstner, J. Org. Chem. 1998, 63, 8806-8814.
45. D. Lenoir, Synthesis 1977, 553-554.
46. M. M. Cid, J. A. Seijas, M. C. Villaverde, L. Castedo, Tetrahedron 1988, 44, 6197-6200.
47. C. Lee, J. S. Yu, H. Lee, J. Heterocycl. Chem. 2002, 39, 1207-1217.
48. J. H. Gorvin, J. Chem. Soc. 1959, 678-680.
49. M. M. G. Antonisse, B. H. M. Snellink-Ruël, I. Yigit, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 9034-9038.
50. T. Satoh, N. Mitsuo, M. Nishiki, Y. Inoue, Y. Ooi, Chem. Pharm. Bull. 1981, 29, 1443-1445.
51. A similar phenomenon has been observed by Ivanov. For details see: R. I. Gearba, M. Lehmann, J. Levin, D. A. Ivanov, M. H. J. Koch, J. Barbera, M. G. Debije, J. Piris, Y. H. Geerts, Adv. Mater. 2003, 15, 1614-1618.
52. W. Pisula, M. Kastler, D. Wasserfallen, T. Pakula, K. Müllen, J. Am. Chem. Soc. 2004, 126, 8074-8075.
53. M. Kodama, Y. Shiobara, H. Sumitomo, K. Matsumura, M. Tsukamoto, C. Harada, J. Org. Chem. 1988, 53, 72-77.
54. 1/2} F denotes the Faraday constant, R the gas constant and T the temperature.
55. A. S. Baranski, W. R. Fawcett, C. M. Gilbert, Anal. Chem. 1985, 57, 166-170.
56. F. Ammar, J. M. Savéant, J. Electroanal. Chem. Interfacial Electrochem. 1973, 47, 115-125.
57. Peaks of chemically irreversible voltammetric waves are shifted with respect to where they would appear in the absence of a subsequent chemical reaction, and the amount of this shift depends on the (unknown) equilibrium constant of the subsequent chemical process. See: R. S. Nicholson, I. Shain, Anal. Chem. 1964, 36, 706-723.
58. D. Lin-Vien, N. B. Colthup, W. G. Fateley, J. G. Grasselli, The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; Academic Press: San Diego, 1991.
59. M. Krejcik, M. Danek, F. Hartl, J. Electroanal. Chem. 1991, 317, 179-187.