Synthesis and characterization of the electronic and electrochemical properties of thienylenevinylene oligomers with multinanometer dimensions

Journal of the American Chemical Society

Volumn 120, Issue 32, 1998, Pages 8150-8158

  Jestin, Isabelle ^a   Frère, Pierre ^a   Mercier, Nicolas ^a   Levillain, Eric ^a   Stievenard, Didier ^b   Roncali, Jean ^a  

^a UNIVERSITÉ D'ANGERS   (France)

^b INSTITUT D ELECTRONIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER; THIENYLENEVINYLENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ELECTROCHEMICAL ANALYSIS; ELECTRONICS; LINEAR SYSTEM; MOLECULAR DYNAMICS; OPTICS; ORGANIC CHEMISTRY; POTENTIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032547276     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980603z     Document Type: Article

References (71)

1. (a) Handbook of Conducting Polymers; Elsenbaumer R. L., Skotheim, T., Reynolds, J. R., Eds.; Dekker: New York, 1998.
2. (b) Roncali, J. Chem. Rev. 1997, 97, 173.
3. (c) Tour, J. M. Chem. Rev. 1996, 96, 537.
4. (a) Tasaka, S.; Katz, H. E.; Hutton, R. S.; Orenstein, J.; Frederickson, G. H.; Wane, T. T. Synth. Met. 1986, 16, 17.
5. (b) Gamier, F.; Hajlaoui, R.; Yassar, A.; Srivastava, P. Science 1994, 265, 1684.
6. (c) Dodabalapur, A.; L. Torsi, L.; Katz, H. E. Science 1995, 268, 270.
7. (d) Katz, H. E. J. Mater. Chem. 1997, 7, 369.
8. Geiger, F.; Stoldt, M.; Schweizer, R.; Bäuerle, P.; Umbach, E. Adv. Mater. 1993, 5, 922.
9. (a) Jones, D.; Guerra, M.; Favaretto, L.; Modelli, A.; Fabrizio, M.; Distefano, G. J. Phys. Chem. 1990, 94, 5761.
10. (b) Caspar, J. V.; Ramamurthy, V.; Corbin, D. R. J. Am. Chem. Soc. 1991, 113, 600.
11. (c) Havinga, E. E.; Rotte, I.; Meijer, E. W.; ten Hoeve, W.; Wynberg, H. Synth. Met. 1991, 41, 473.
12. (d) Bäuerle, P. Adv. Mater. 1992, 4, 102.
13. (e) Guay, J.; Kasai, P.; Diaz, A.; Wu, R.; Tour, J. M.; Dao, L. H. Chem. Mater. 1992, 4, 1097.
14. (f) Bäuerle, P.; Fisher, T.; Bidlingmeier, B.; Stabel, A.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 303.
15. (g) Martin, R. E.; Gubler, U.; Boudon, C.; Gramlich, V.; Bosshard, C.; Gisselbrecht, J.-P.; Günter, P.; Gross, M.; Diederich, F. Chem. Eur. J. 1997, 3, 1505.
16. (h) Stalmach, U.; Kolshorn, H.; Brehm, I.; Meier, H. Liebigs Ann. Chem. 1996, 1449.
17. a) Lehn, J. M. Angew. Chem., Int. Ed. Engl. 1988, 27, 90.
18. (b) Aviram, A. J. Am. Chem. Soc. 1988, 110, 5687.
19. (c) Effenberger, F.; Schlosser, H.; Bäuerle, P.; Maier, S.; Port, H.; Wolf, H. C. Angew. Chem., Int. Ed. Engl. 1988, 27, 281.
20. (d) Guay, J.; Diaz, A.; Wu, R.; Tour, J. M. J. Am. Chem. Soc. 1993, 115, 1869.
21. (e) Beley, M.; Chodorowski-Kimmes, Collin, J. P.; Lainé, P.; Launay, J. P.; Sauvage, J. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1775.
22. (f) Grosshenny, V.; Harriman, A.; Ziessel, R. Angew. Chem., Int Ed Engl. 1995, 34, 1100.
23. (g) Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
24. (h) Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906.
25. (a) Alberti, A.; Favaretto, L.; Seconi, G. J. Chem. Soc., Perkin Trans. 2 1990, 931.
26. (b) Chadwick, J. E. Kohler, B. E. J. Phys. Chem. 1994, 98, 3631.
27. (c) Distefano, G.; Da Colle, M.; Jones, D.; Zambianchi, M.; Favaretto, L.; Modelli, A. J. Phys. Chem. 1993, 97, 3504.
28. (d) Orti, E.; Viruela, P. M.; Sanchez-Marin, J.; Tomas, F. J. Phys. Chem. 1995, 99, 4955.
29. (e) Horne, J. C.; Blanchard, G. J.; LeGoff, E. J. Am. Chem. Soc. 1995, 117, 955.
30. (a) Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. Tetrahedron Lett. 1993, 34, 1747.
31. (b) Rao, V. P.; Cai, Y. M.; Jen, A. K.-Y. J. Chem. Soc., Chem. Commun. 1994, 1689.
32. (a) Roncali, J. J. Mater. Chem. 1997, 12, 2037.
33. (b) Elandaloussi, E.; Frère, P.; Roncali, J.; Richomme, P.; Jubault, M.; Gorgues, A. Adv. Mater. 1995, 7, 390.
34. (c) Elandaloussi, E.; Frère, P.; Roncali, J. Tetrahedron Lett. 1996, 37, 6121.
35. (a) Kossmehl, G. Ber. Bunsen-Ges. Phys. Chem. 1979, 83, 417.
36. (b) Kossmehl, G.; Härtel, M.; Manecke, G. Makromol. Chem. 1970, 131, 15.
37. (a) Nakayama J.; Fujimori, T. Heterocycles 1991, 32, 991.
38. (b) Spangler, C. W.; Liu, P.-K. Synth. Met. 1991, 44, 259.
39. (c) Spangler, C. W.; Bryson, P.; Liu, P.-K.; Dalton, L. R. J. Chem. Soc., Chem. Commun. 1992, 253.
40. Hu, Z.; Atwood, J. L.; Cava, M. P. J. Org. Chem. 1994, 59, 8071.
41. (a) Elandaloussi, E.; Frère, P.; Roncali, J. Chem. Commun. 1997, 301.
42. (b) Elandaloussi, E.; Frère, P.; Richommme, P.; Orduna, J.; Garin, J.; Roncali, J. J. Am. Chem. Soc. 1997, 119, 10774.
43. Preliminary communication: Jestin, I.; Frère, P.; Blanchard, P.; Roncali, J. Angew. Chem., Int. Ed. 1998, 37, 942.
44. McMurry, J. E. Chem. Rev. 1989, 89, 1513. Fürstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2443.
45. McMurry, J. E. Chem. Rev. 1989, 89, 1513. Fürstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2443.
46. Tamao, K.; Odama, S.; Nakasima, I.; Kumada, M.; Minato, A.; Suzuki, K. Tetrahedron 1982, 8, 3347.
47. Hyperchem 5.0, Hypercube Inc.. Waterloo, Canada, 1996.
48. g by extrapolation to zero of the low-energy absorption edge, although these procedures lead to larger values than the previous one.
49. g by extrapolation to zero of the low-energy absorption edge, although these procedures lead to larger values than the previous one.
50. Rughooputh, S. D. D. V.; Hotta, S.; Heeger, A. J.; Wudl, F. J. Polym. Sci. 1987, 25, 1071.
51. (a) Yamada, S.; Tokito, S.; Tsuisui., T.; Saito, S. Chem. Commun. 1987, 1448.
52. (b) Barker, J. Synth. Met. 1989, 32, 43.
53. Stenger-Smith, J. D.; Lenz, R. W.; Wegner, G. Polymer 1989, 30, 1048. Shah, H. V.; McGhie, A. R.; Arbuckle, G. A. Thermochim. Acta 1996, 287, 319. Herold, M.; Gmeiner, J.; Schwoerer, M. Acta Polym. 1996, 47, 436. Mertens, R.; Nagels, P.; Callaerts, R. Synth. Met. 1997, 84, 977.
54. Stenger-Smith, J. D.; Lenz, R. W.; Wegner, G. Polymer 1989, 30, 1048. Shah, H. V.; McGhie, A. R.; Arbuckle, G. A. Thermochim. Acta 1996, 287, 319. Herold, M.; Gmeiner, J.; Schwoerer, M. Acta Polym. 1996, 47, 436. Mertens, R.; Nagels, P.; Callaerts, R. Synth. Met. 1997, 84, 977.
55. Stenger-Smith, J. D.; Lenz, R. W.; Wegner, G. Polymer 1989, 30, 1048. Shah, H. V.; McGhie, A. R.; Arbuckle, G. A. Thermochim. Acta 1996, 287, 319. Herold, M.; Gmeiner, J.; Schwoerer, M. Acta Polym. 1996, 47, 436. Mertens, R.; Nagels, P.; Callaerts, R. Synth. Met. 1997, 84, 977.
56. Stenger-Smith, J. D.; Lenz, R. W.; Wegner, G. Polymer 1989, 30, 1048. Shah, H. V.; McGhie, A. R.; Arbuckle, G. A. Thermochim. Acta 1996, 287, 319. Herold, M.; Gmeiner, J.; Schwoerer, M. Acta Polym. 1996, 47, 436. Mertens, R.; Nagels, P.; Callaerts, R. Synth. Met. 1997, 84, 977.
57. Meier, H.; Stalmach, U.; Kolshorn, H. Acta Polym. 1997, 48, 379.
58. (a) Roncali, J.; Thobie-Gautier, C.; Elandaloussi, E.; Frère, P. J. Chem. Soc., Chem. Commun. 1994, 2249.
59. (b) Catellani, M.; Luzzati, S.; Musco, A.; Speroni, F. Synth. Met. 1994, 62, 223.
60. (a) Meerholz, K.; Heinze, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 692.
61. (b) Meerholz, K.; Gregorius, H.; Müllen, K.; Heinze J. Adv. Mater. 1994, 6, 671.
62. (c) Meerholz, K.; Heinze, J. Electrochim. Acta 1996, 41, 1839.
63. (a) Hill, M. G.; Mann, K. R.; Miller, L. L.; Penneau, J. F. J. Am. Chem. Soc. 1992, 114, 2728.
64. (b) Hill, M. G.; Mann, K. R.; Miller, L. L.; Penneau, J. F.; Zinger, B. Chem. Mater. 1992, 4, 1106.
65. (c) Zinger, B.; Mann, K. R.; Hill, M. G.; Miller, L. L. Chem. Mater. 1992, 4, 1113.
66. (d) Yu, Y.; Gunic, E.; Zinger, B.; Miller, L. L. J. Am. Chem. Soc. 1996, 118, 1013.
67. (e) Graf, D. D.; Duan, R. G. Campbell, J. P.; Miller, L. L.; Mann, K. R. J. Am. Chem. Soc. 1997, 119, 5888.
68. (a) Bäuerle, P.; Segelbacher, U.; Maier, A.; Mehring, M. J. Am. Chem Soc. 1993, 115, 10217.
69. (b) Hapiot, P.; Audetot, P.; Monnier, K.; Pernaut, J.-M.; Garcia, P. Chem. Mater. 1994, 6, 1549.
70. (a) Brisset, H.; Blanchard, P.; Illien, B.; Riou, A.; Roncali, J. Chem. Commun. 1997, 569.
71. (b) Blanchard, P.; Brisset, H.; Illien, B.; Riou, A.; Roncali, J. J. Org. Chem. 1997, 62, 2401.