A mixed fullerene - ferrocene thermotropic liquid crystal: Synthesis, liquid-crystalline properties, supramolecular organization and photoinduced electron transfer

Chemistry - A European Journal

Volumn 7, Issue 12, 2001, Pages 2595-2604

  Even, Michaël ^a   Heinrich, Benoit ^b   Guillon, Daniel ^b   Guldi, Dirk M ^c   Prato, Maurizio ^d   Deschenaux, Robert ^a  

^a UNIVERSITY OF NEUCHÂTEL   (Switzerland)

^b INSTITUT DE PHYSIQUE ET CHIMIE DES MATÉRIAUX DE STRASBOURG   (France)

^c UNIVERSITY OF NOTRE DAME   (United States)

^d UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Electron transfer; Ferrocene; Fullerenes; Liquid crystals; Materials science

Indexed keywords

CHOLESTEROL; FERROCENE; FULLERENE;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; LIQUID CRYSTAL; SPECTROMETRY; STRUCTURE ANALYSIS; SYNTHESIS; VOLUMETRY; X RAY DIFFRACTION;

EID: 0035907944     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010618)7:12<2595::AID-CHEM25950>3.0.CO;2-A     Document Type: Article

References (71)

1. a) M. Prato, J. Mater. Chem. 1997, 7, 1097;
2. b) M. Prato, Top. Curr. Chem. 1999, 199, 173.
3. a) K. E. Geckeler, A. Hirsch, J. Am. Chem. Soc. 1993, 115, 3850;
4. b) C. J. Hawker, Macromolecules 1994, 27, 4836;
5. c) C. Weiss, C. Friedrich, R. Mülhaupt, H. Frey, Macromolecules 1995, 28, 403;
6. d) B. Liu, E. Bunker, Y.-P. Sun, Chem. Commun. 1996, 1241;
7. e) Y.-P. Sun, B. Liu, D. K. Moton, Chem. Commun. 1996, 2699;
8. f) Y. Ederle, C. Mathis, Macromolecules 1997, 30, 4262;
9. g) H. Okamura, N. Ide, M. Minoda, K. Komatsu, T. Fukuda, Macromolecules 1998, 31, 1859;
10. h) Z. Y. Wang, L. Kuang, X. S. Meng, J. P. Gao, Macromolecules 1998, 31, 5556;
11. i) L. Dai, A. W. H. Mau, X. Zhang, J. Mater. Chem. 1998, 8, 325;
12. j) A. Kraus, K. Müllen, Macromolecules 1999, 32, 4214.
13. a) K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, F. Wudl, G. Srdanov, S. Shi, M. Kao, J. Am. Chem. Soc. 1993, 115, 9836;
14. b) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Chem. Commun. 1994, 925;
15. c) X. Camps, H. Schönberger, A. Hirsch, Chem. Eur. J. 1997, 3, 561;
16. d) F. Cardullo, F. Diederich, L. Echegoyen, T. Habicher, N. Jayaraman, R. M. Leblanc, J. F. Stoddart, S. Wang, Langmuir 1998, 14, 1955;
17. e) M. Brettreich, A. Hirsch, Tetrahedron Lett. 1998, 39, 2731;
18. f) N. Armaroli, C. Boudon, D. Felder, J.-P. Gisselbrecht, M. Gross, G. Marconi, J.-F. Nicoud, J.-F. Nierengarten, V. Vicinelli, Angew. Chem. 1999, 111, 3895;
19. Angew. Chem. Int. Ed. 1999, 38, 3731;
20. g) J.-F. Nierengarten, D. Felder, J.-F. Nicoud, Tetrahedron Lett. 1999, 40, 269;
21. h) J.-F. Nierengarten, D. Felder, J.-F. Nicoud, Tetrahedron Lett. 1999, 40, 273;
22. i) J.-F. Nierengarten, D. Felder, J.-F. Nicoud, Tetrahedron Lett. 2000, 41, 41;
23. j) J.-F. Nierengarten, Chem. Eur. J. 2000, 6, 3667.
24. a) M. Maggini, G. Scorrano, M. Prato, G. Brusatin, P. Innocenzi, M. Guglielmi, A. Renier, R. Signorini, M. Meneghetti, R. Bozio, Adv. Mater. 1995, 7, 404;
25. b) R. Signorini, M. Zerbetto, M. Meneghetti, R. Bozio, M. Maggini, C. De Faveri, M. Prato, G. Scorrano, Chem. Commun. 1996, 1891;
26. c) M. Maggini, C. De Faveri, G. Scorrano, M. Prato, G. Brusatin, M. Guglielmi, M. Meneghetti, R. Signorini, R. Bozio, Chem. Eur. J. 1999, 5, 2501;
27. d) A. Kraus, M. Schneider, A. Gügel, K. Müllen, J. Mater. Chem. 1997, 7, 763.
28. a) M. Hetzer, S. Bayerl, X. Camps, O. Vostrowsky, A. Hirsch, T. M. Bayerl, Adv. Mater. 1997, 9, 913;
29. b) M. Hetzer, H. Clausen-Schaumann, S. Bayerl, T. M. Bayerl, X. Camps, O. Vostrowsky, A. Hirsch, Angew. Chem. 1999, 111, 2103;
30. Angew. Chem. Int. Ed. 1999, 38, 1962;
31. c) M. Breittreich, S. Burghardt, S. Böttcher, T. Bayerl, S. Bayerl, A. Hirsch, Angew. Chem. 2000, 112, 1915;
32. Angew. Chem. Int. Ed. 2000, 39, 1845.
33. D. M. Guldi, Chem. Commun. 2000, 321.
34. H. Imahori, Y. Sakata, Eur. J. Org. Chem. 1999, 2445.
35. a) N. S. Sariciftci, L. Smilowitz, A. J. Heeger, F. Wudl, Science 1992, 258, 1474;
36. b) L. Pasimeni, A. L. Maniero, M. Ruzzi, M. Prato, T. Da Ros, G. Barbarella, M. Zambianchi, Chem. Commun. 1999, 429.
37. G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science, 1995, 270, 1789;
38. b) J.-F. Nierengarten, J.-F. Eckert, J.-F. Nicoud, L. Ouali, V. Krasnikov, G. Hadziioannou, Chem. Commun. 1999, 617.
39. K. Hutchison, J. Gao, Y. Rubin, F. Wudl, J. Am. Chem. Soc. 1999, 121, 5611.
40. T. Chuard, R. Deschenaux, Helv. Chim. Acta 1996, 79, 736.
41. R. Deschenaux, M. Even, D. Guillon, Chem. Commun. 1998, 537.
42. B. Dardel, R. Deschenaux, M. Even, E. Serrano, Macromolecules 1999, 32, 5193.
43. T. Chuard, R. Deschenaux, A. Hirsch, H. Schönberger, Chem. Commun. 1999, 2103.
44. a) C. Bingel, Chem. Ber. 1993, 126, 1957;
45. b) J.-P. Bourgeois, F. Diederich, L. Echegoyen, J.-F. Nierengarten, Helv. Chim. Acta 1998, 81, 1835.
46. N. Tirelli, F. Cardullo, T. Habicher, U. W. Suter, F. Diederich, J. Chem. Soc. Perkin Trans. 2 2000, 193.
47. D. Felder, B. Heinrich, D. Guillon, J.-F. Nicoud, J.-F. Nierengarten, Chem. Eur. J. 2000, 6, 3501.
48. a) R. Deschenaux, M. Schweissguth, A.-M. Levelut, Chem. Commun. 1996, 1275;
49. b) R. Deschenaux, M. Schweissguth, M.-T. Vilches, A.-M. Levelut, D. Hautot, G. L. Long, D. Luneau, Organometallics 1999, 18, 5553.
50. D. M. Guldi, M. Maggini, G. Scorrano, M. Prato, J. Am. Chem. Soc. 1997, 119, 974.
51. R. Deschenaux, C. Masoni, H. Stoeckli-Evans, S. Vaucher, J. Ketterer, R. Steiger, A. L. Weisenhorn, J. Chem. Soc. Dalton Trans. 1994, 1051.
52. U. Jonas, F. Cardullo, P. Belik, F. Diederich, A. Gügel, E. Harth, A Hermann, L. Isaacs, K. Müllen, H. Ringsdorf, C. Thielgen, P. Uhlmann, A. Vasella, C. A. A. Waldraff, M. Walter, Chem. Eur. J. 1995, 1, 243.
53. D. Guillon, A. Skoulios, J. de Physique 1976, 37, 797.
54. R. Deschenaux, I. Jauslin, U. Scholten, F. Turpin, D. Guillon, B. Heinrich, Macromolecules 1998, 31, 5647.
55. D. Guillon,. A. Skoulios, Mol. Cryst. Liq. Cryst. 1977, 39, 31.
56. P. Seurin, D. Guillon, A. Skoulios, Mol. Cryst. Liq. Cryst. 1980, 61, 185.
57. G. Poeti, E. Fanelli, G. Torquati, D. Guillon, Il Nuovo Cimento, Series 1, Vol. 2D, 1983, 1335.
58. a) D. M. Guldi, H. Hungerbühler, K.-D. Asmus, J. Phys. Chem. 1995, 99, 9380;
59. b) D. M. Guldi, K.-D. Asmus, J. Phys. Chem. A. 1997, 101, 1472;
60. c) D. M. Guldi, M. Prato, Acc. Chem. Res. 2000, 33, 695.
61. a) T. W. Ebbesen, K. Tanigaki, S. Kuroshima, Chem. Phys. Lett. 1991, 181, 501;
62. b) N. M. Dimitrijevic, P. V. Kamat, J. Phys. Chem. 1992, 96, 4811;
63. c) R. B. Weisman in Optical and Electronical Properties of Fullerenes and Fullerene-based Materials (Eds.; J. Shinar, Z. V. Vardeny), Marcel Dekker, New York, 2000, pp. 83-117.
64. M. Faraggi, D. Weinraub, F. Broitman, M. R. DeFelippis, M. H. Klapper, Radiat. Phys. Chem. 1988, 32, 293.
65. Y. S. Sohn, D. N. Hendrickson, H. B. Gray, J. Am. Chem. Soc. 1971, 93, 3603.
66. W. G. Herkstroeter, J. Am. Chem. Soc. 1975, 97, 4161.
67. E. Dietel, A. Hirsch, J. Zhou, A. Rieker, J. Chem. Soc. Perkin Trans. 2 1998, 1357.
68. We thank Prof. Francesco Paolucci for providing these data to us.
69. A. J. Kovacs, Ric. Sci. Suppl. 1955, 25, 668.
70. D. Guillon, PhD thesis, University of Strasbourg, 1976;
71. D. Guillon, A. Skoulios, R. Acad. Sci. Paris 1974, C278, 1974.