Synthesis of oligothienylfullerrenes

Synthesis

Volumn , Issue 9, 1998, Pages 1372-1379

  Effenberger, Franz ^a   Grube, Gunther ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Donor acceptor system; Fullerenes; Intramolecular electron transfer; Oligothiophenes; Suzuki coupling

Indexed keywords

FULLERENE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031705745     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-6090     Document Type: Article

References (62)

1. Grube, G. Dissertation, University of Stuttgart, 1997.
2. Effenberger, F.; Schlosser, H.; Bäuerle, P.; Maier, S.; Port, H.; Wolf, H.C. Angew. Chem. 1988, 100, 274;
3. Angew. Chem., Int. Ed. Engl. 1988, 27, 281.
4. (a) Effenberger, F.; Wolf, H.C. New J. Chem. 1991, 75, 117.
5. (b) Holl, N.; Port, H.; Wolf, H.C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215.
6. (a) Würthner, F.; Vollmer, M.S.; Effenberger, F.; Emele, P.; Meyer, D.U.; Port, H.; Wolf, H.C. J. Am. Chem. Soc. 1995, 117, 8090.
7. (b) Vollmer, M.S.; Effenberger, F.; Stümpfig, T.; Hartschuh, A.; Port, H.; Wolf, H.C. J. Org. Chem., in press
8. (a) Effenberger, F.; Niesert, C.-P. Synthesis 1992, 1137.
9. (b) Hirsch, T.; Port, H.; Wolf, H.C.; Miehlich, B.; Effenberger, F. J. Phys. Chem. B 1997, 101, 4225.
10. (a) Haddon, R.C.; Brus, L.E.; Raghavachari, K. Chem. Phys. Lett. 1986, 125, 459.
11. (b) Allemand, P.-M.; Koch, A.; Wudl, F.; Rubin, Y.; Diederich, F.; Alvarez, M.M.; Anz, S.J.; Whetten, R.L. J. Am. Chem. Soc. 1991, 113, 1050.
12. Arbogast, J.W.; Foote, C.S.; Kao, M. J. Am. Chem. Soc. 1992, 114, 2277.
13. Mackay, R.A.; Laudolph, J.R.; Poziomek, E.J. J. Am. Chem. Soc. 1971, 93, 5026.
14. (a) Foote, C.S. Top. Curr. Chem. 1994, 169, 347.
15. (b) Sariciftci, N.S. Prog. Quant. Electron. 1995, 19, 131.
16. Benatti, M.; Grupp, A.; Bäuerle, P.; Mehring, M. Chem. Phys. 1994, 185, 221.
17. (a) Williams, R.M.; Zwier, J.M.; Verhoeven, J.M. J. Am. Chem. Soc. 1995, 117, 4093.
18. (b) Liddell, P.A.; Sumida, J.P.; MacPherson, A.N.; Noss, L.; Seely, G.R.; Clark, K.N.; Moore, A.L.; Moore, T.A.; Gust, D. Photochem. Photobiol. 1994, 60, 537.
19. (a) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
20. (b) Williams, R.M.; Koeberg, M.; Lawson, J.M.; An, Y.-Z.; Rubin, Y.; Paddon-Row, M.N.; Verhoeven, J.M. J. Org. Chem. 1996, 61, 5055.
21. (c) Lawson, J.M.; Oliver, A.M.; Rothenfluh, D.F.; An, Y.-Z.; Ellis, G.A.; Ranasinghe, M.G.; Khan, S.I.; Franz, A.G.; Ganapathi, P.S.; Shephard, M.J.; Paddon-Row, M.N.; Rubin, Y. J. Org. Chem. 1996, 61, 5032.
22. (d) Liddell, P.A.; Kuciauskas, D.; Sumida, J.P.; Nash, B.; Nguyen, D.; Moore, A.L.; Moore, T.A.; Gust, D. J. Am. Chem. Soc. 1997, 119, 1400.
23. (e) Guldi, D.M.; Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1997, 119, 974.
24. (f) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771.
25. (g) Kuciauscas, D.; Lin, S.; Seely, G.R.; Moore, A.L.; Moore, T.A.; Gust, D. J. Phys. Chem. 1996, 100, 15926.
26. (h) Imahori, H.; Hagiwara, K.; Akiyama, T.; Taniguchi, S.; Okada, T.; Sakata, Y. Chem. Lett. 1995, 265.
27. (i) Drovetskaya, T.; Reed, C.A.; Boyd, P. Tetrahedron Lett. 1995, 36, 7971.
28. (j) Imahori, H.; Cardoso, S.; Tatman, D.; Lin, S.; Noss, L.; Seely, G.R.; Sereno, L.; de Silber, J.C.; Moore, T.A.; Moore, L.A.; Gust, D. Photochem. Photobiol. 1995, 62, 1009.
29. (k) Sariciftci, N.S.; Wudl, F.; Heeger, A.J.; Maggini, M.; Scorrano, G.; Prato, M.; Bourassa, J.; Ford, P.C. Chem. Phys. Lett. 1995, 247, 510.
30. Imahori, H.; Yamada, K.; Hasegawa, M.; Taniguchi, S.; Okada, T.; Satata, Y. Angew. Chem. 1997, 109, 2740;
31. Angew. Chem., Int. Ed. Engl. 1997, 36, 2626.
32. Hirsch, A.; Soi, A.; Karfunkel, H.R. Angew. Chem. 1992, 104, 808;
33. Angew. Chem., Int. Ed. Engl. 1992, 31, 766.
34. (a) Hirsch A. In The Chemistry of the Fullerenes; Thieme: Stuttgart, 1994 pp 80.
35. (b) Sliwa, W. Fullerene Sci. Technol. 1995, 3, 243.
36. (c) Belik, P.; Gügel, A.; Spickermann, J.; Müllen, K. Angew. Chem. 1993, 105, 95;
37. Angew. Chem., Int. Ed. Engl. 1993, 32, 78.
38. (d) Eguchi, S.; Ohno, M.; Kojima, S.; Koide, N.; Yashiro, A.; Shirakawa, Y.; Ishida, H. Fullerene Sci. Technol. 1996, 4, 303.
39. (e) Illescas, B.M.; Martín, N.; Seoane, C. J. Org. Chem. 1997, 62, 7585.
40. (f) Nakamura, Y.; Minowa, T.; Tobita, S.; Shizuka, H.; Nishimura, J. J. Chem. Soc., Perkin Trans. 2 1995, 2351.
41. (a) Chung, W.-S.; Liu, J.-H. J. Chem. Soc., Chem. Commun. 1997, 205.
42. (b) Herrera, A.; Martinez, R.; Gonzales, B.; Illescas, B.M.; Martin, N.; Seoane, C. Tetrahedron Lett. 1997, 38, 4873.
43. (c) Tomé, A.C.; Enes, R.F.; Cavaleiro, J.A.S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557.
44. (d) Fernandez-Paniagua, U.M.; Illescas, B.M.; Martin, N.; Seoane, C. J. Org. Chem. 1997, 62, 3705.
45. (e) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125.
46. (f) Fernandez-Paniagua, U.M.; Illescas, B.M.; Martin, N.; Seoane, C. J. Chem. Soc., Perkin Trans 1 1996, 1077.
47. (g) Ohno, M.; Koide, N.; Sato, H.; Eguchi, S. Tetrahedron 1997, 53, 9075.
48. Heffner, R.J.; Joullié, M.M. Synth. Commun. 1991, 21, 1055.
49. (a) Chaloner, L.M.; Crew, A.P.A.; O'Neill, P.M.; Storr, R.C. Tetrahedron 1992, 48, 8101.
50. (b) MacDowell, D.W.H.; Patrick, T.B. J. Org. Chem. 1966, 31, 3592.
51. (c) Chou, T.; Tsai, C.-Y. J. Chem. Soc., Chem. Commun. 1991, 1287.
52. (a) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
53. (b) Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. 1981, 22, 127.
54. (c) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
55. Johnson, J.R.; van Campen, M.G.; Grummit, O. J. Am. Chem. Soc. 1938, 60, 111.
56. (a) We thank graduate student J. Münter, University of Stuttgart, for the preparation of this compound (1995).
57. (b) Vollmer, M.S. Dissertation, University of Stuttgart, 1996.
58. Hoey, M.D.; Dittmer, D.C. J. Org. Chem. 1991, 56, 1947.
59. Coulson, D.R. Inorg. Synth. 1972, 13, 121.
60. Müller, H.; Petersen, J.; Strohmaier, R.; Gompf, B.; Eisenmenger, W.; Vollmer, M.S.; Effenberger, F. Adv. Mater. 1996, 8, 733.
61. van Hecke, G.R.; Horrocks, W.D. Inorg. Chem. 1966, 5, 1968.
62. Chou, T.; Wang, C.-T. Tetrahedron 1996, 52, 12459.