Copolymers of 3,4-ethylenedioxythiophene and of pyridine alternated with fluorene or phenylene units: Synthesis, optical properties, and devices

Macromolecules

Volumn 37, Issue 11, 2004, Pages 4087-4098

  Aubert, Pierre Henri ^a,d   Knipper, Martin ^b   Groenendaal, Lambertus ^c   Lutsen, Laurence ^a   Manca, Jean ^a   Vanderzande, Dirk ^a,b  

^a HASSELT UNIVERSITY   (Belgium)

^b HASSELT UNIVERSITY   (Belgium)

^c RM D ^*  (Belgium)

^d UNIVERSITÉ DE CERGY PONTOISE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC VOLTAMMETRY; ELECTROLUMINESCENCE; ELECTRONIC STRUCTURE; FLUORINE COMPOUNDS; OPTICAL PROPERTIES; ORGANIC SOLVENTS; PHOTOLUMINESCENCE; POLYCONDENSATION; SIZE EXCLUSION CHROMATOGRAPHY; SYNTHESIS (CHEMICAL);

FLUORENE; PHENYLENE; PYRIDINE; UV-VIS METHODS;

COPOLYMERS;

EID: 2942675059     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma030540r     Document Type: Article

References (72)

1. (a) Shirakawa, H.; Lewis, E. J.; MacDiarmid, A. G.; Chiang, C. K.; Heeger, A. J. J. Chem. Soc., Chem. Commun. 1977, 578.
2. (b) Chiang, C. K.; Fincher, C. R.; Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Louis, E. J.; Gau, S. C.; MacDiarmid, A. G. Phys. Rev. Lett. 1977, 39, 1098,
3. Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; John Wiley & Sons: Chichester, 1997; Vols. 1-4.
4. Polymeric and Organic Electronic Materials and Applications; Epstein, A. J., Yang, Y., Guest Eds.; MRS Bull. 1997, 22, 13.
5. (a) Photonic and Optoelectronic Polymers; Jenekhe, S. A., Wynne, K. J., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1997.
6. (b) Chromogenic Phenomena in Polymers: Tunable Optical Properties; Jenekhe, S. A., Kiserow, D. J., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 2003; in press.
7. Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998.
8. Roncali, J. Chem. Rev. 1997, 97, 173.
9. (a) Brabec, C. J.; Cravino, A.; Zerza, G.; Sariciftci, N. S.; Kiebooms, R.; Vanderzande, D.; Hummelen, J. C. J. Phys. Chem. B 2001, 105, 1528.
10. (b) Munsters, T.; Martens, T.; Goris, L.; Vrindts, V.; Manca, J.; Lutsen, L.; DeCeunick, W.; Vanderzande, D.; De Schepper, L.; Gelan, J,; Sariciftci, N. S. Thin Solid Films 2002, 403-404, 247.
11. (c) Manca, J. V.; Goris, L.; Kesters, E.; Lutsen, L.; Martens, T.; Haenen, K.; Nesladek, M.; Sanna, O.; Vanderzande, D.; D'Haen, J.; De Schepper, L. MRS Proc. 769, 361-367.
12. (a) Burroughes, J. H.; Bradley, D. D.; Marks, R. N.; MacKay, K.; Friends, R. H.; Burn, P. L.; Holmes, A. B. Nature (London) 1990, 347, 539.
13. (b) Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature (London) 1992, 357, 477.
14. Grem, G.; Leditzky, G.; Ullrich, B. Adv. Mater. 1992, 4, 36.
15. Davey, A. P.; Elliott, S.; O'Connor, O.; Blau, W. J. Chem. Soc., Chem. Commun. 1995, 1433.
16. Yang, Y.; Pei, Q.; Heeger, A. J. J. Appl. Phys. 1996, 79, 934.
17. Ohmori, Y.; Uchida, M.; Muro, K.; Yoshino, K. Jpn. J. Appl. Phys. 1991, 30, L1941,
18. (b) Pei, Q.; Yang, Y. J. Am. Chem. Soc. 1996, 118, 7416.
19. Ranger, M.; Leclerc, M. J. Chem. Soc., Chem. Commun. 1997, 1597.
20. Ranger, M.; Rondeau, D.; Leclerc, M. Macromolecules 1997, 30, 7686.
21. Wagner, P.; Aubert, P.-H.; Lutsen, L.; Vanderzande, D. Electrochem. Commun. 2002, 4, 912.
22. Liu, B.; Yu, W. L.; Lai, Y. H.; Huang, W. Chem. Mater. 2001, 13, 1984.
23. (a) Hicks, R. G.; Nodwell, M. B. J. Am. Chem. Soc. 2000, 122, 6746.
24. (b) Sotzing, G. A.; Reynolds, J. R.; Steel, P. J. Chem. Mater. 1996, 8, 882.
25. Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906.
26. Ranger, M.; Rondeau, D.; Leclerc, M. Macromolecules 1997, 30, 7686.
27. Becker, H.; Spreitzer, H.; Ibro, K.; Kreuder, W. Macromolecules 1999, 32, 4925.
28. (a) Wang, S.; Oldham, W. J.; Hudack, R. A.; Bazan, G. C J. Am. Chem. Soc. 2000, 122, 5695.
29. (b) Bao, Z.; Chen, Y.; Cai, R.; Yu, L. Macromolecules 1993, 26, 5281.
30. Fuduka, M.; Sawada, M.; Yoshino, K. Jpn. J. Appl. Phys. 1989, 28, L1433.
31. Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906.
32. Parakka, J. P.; Jeevarajan, J. A.; Jeevarajan, A. S.; Kispert, D. L.; Cava, M. P. Adv. Mater. 1996, 8, 54.
33. Coutts, I. G.; Goldschmid, H. R.; Musgrave, O. C. J. Chem. Soc. 1970, 488.
34. Schlüter, A. D. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1533.
35. Wang, F.; Wilson, M. S.; Rauh, D.; Schottland, P.; Thompson, B. C.; Reynolds, J. R. Macromolecules 2000, 33, 2083.
36. Bao, Z.; Chan, W.; Yu, L. Chem. Mater. 1993, 5, 2.
37. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc., 2000, 122, 4020 and ref 1 therein.
38. Shin, D. C.; Ahn, J. H.; Kim, Y. H.; Kwon, S. K. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 3086.
39. Leffrant, S.; Mulazzi, E.; Faulques, E.; Perrin, E. J. Mol. Electron. 1988, 4, 167.
40. Lefrant, S.; Buisson, J.-P.; Eckhardt, H. Synth. Met. 1990, 37, 91.
41. (a) Garreau, S.; Louarn, G.; Lefrant, S.; Buisson, J.-P.; Froyer, G. Synth. Met. 1999, 101, 312.
42. (b) Garreau, S.; Louarn, G.; Lefrant, S.; Buisson, J.-P.; Froyer, G. Macromolecules 1999, 32, 6807.
43. Lapkowski, M.; Prom, A. Synth. Met. 2000, 110, 79.
44. Buisson, J.-P.; Mevellec, J.-Y.; Zeraoui, S.; Lefrant, S. Synth. Met. 1991, 41, 287.
45. Baitou, L. M.; Wery, J.; Dulieu, B.; Lefrant, S.; Buisson, J.-P.; Hamdoune, M. Synth. Met. 1999, 101, 173.
46. Ariu, M.; Lidzey, D. G.; Bradley, D. D. C. Synth. Met. 2000, 111-112, 607.
47. Sykora, M.; Maruszewski, K.; Treffert-Ziemelis, S. M.; Kincaid, J. R. J. Am. Chem. Soc. 1998, 120, 3490.
48. Ng, S. C.; Lu, H. F.; Chan, H. S. O.; Fujii, A.; Laga, T.; Yoshimo, K. Macromolecules 2001, 34, 6895.
49. Sotzing, G. A.; Reynolds, J. R. J. Chem. Soc., Chem. Commun. 1995, 703.
50. (a) Fu, Y.; Cheng, H.; Elsenbaumer, R. L. Chem. Mater. 1997, 9, 1720.
51. (b) Reynolds, J. R.; Kumar, A.; Reddinder, J. L.; Sankaran, B.; Sapp, S. A.; Sotzing, G. A. Synth. Met. 1997, 85, 1295.
52. (a) Larmat, F.; Reynolds, J. R.; Reinhardt, B. A.; Brott, L. L.; Clarson, S. J. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 3627.
53. (b) Sotzing, G. A.; Reddinger, J. L.; Katritsky, A.; Soloducho, J.; Musgrave, R.; Reynolds, J. R. Chem. Mater. 1997, 9, 1578.
54. (a) Sotzing, G. A.; Thomas, C. A.; Reynolds, J. R. Macromolecules 1998, 32, 3750.
55. (b) Sotzing, G. A.; Thomas, C. A.; Reynolds, J. R. Macromolecules 1998, 32, 3750.
56. (c) Sotzing, G. A.; Thomas, C. A.; Reynolds, J. R. Macromolecules 1998, 32, 3750.
57. (d) Irvin, J. A.; Piroux, F.; Morvant, M. C.; Robertshaw, V. L.; Angerhofer, A.; Reynolds, J. R. Synth. Met. 1999, 102, 965.
58. (a) Zotti, G.; Schiavon, G.; Zecchin, S.; Berlin, A. Synth. Met. 1998, 97, 245.
59. (b) Zotti, G.; Schiavon, G.; Zecchin, S.; Groenendaal, L. Chem. Mater. 1999, 11, 3624.
60. (a) Turbiez, M.; Frère, P.; Blanchard, P.; Roncali, J. Tetrahedron. Lett. 2000, 41, 5521.
61. (b) Zotti, G.; Zecchin, S.; Schiavon, G.; Berlin, A.; Huchet, L.; Roncali, J. J. Electroanal. Chem. 2001, 506, 106.
62. Groenendaal, L.; Aubert, P.-H.; Waybright, S. M.; Zotti, G.; Reynolds, J. R. Adv. Mater. 2003, 11, 855.
63. Groenendaal, L.; Jonas, F.; Freitag, D.; Pielartziek, H.; Reynolds, J. R. Adv. Mater. 2000, 12, 481.
64. Donat-Bouillut, A.; Lévesque, I.; Tao, Y.; D'Ioro, M.; Beaupré, S.; Blondin, P.; Ranger, M.; Bouchard, J.; Leclerc, M. Chem. Mater. 2000, 12, 1931.
65. Stephan, O.; Tran-Van, F.; Chevrot, C. Synth. Met. 2002, 131, 31.
66. Sehwedeman, I.; Hwang, J.; Welsh, D. M.; Tanner, D. B.; Reynolds, J. R. Adv. Mater. 2001, 13, 634.
67. Bennet, R. B.; Kokonasku, W. E.; Hannan, M. J.; Boxall, L. G. US Patent 5, 446, 577, 1995.
68. Chandrasekhar, P. US Patent 5,995,273, 1999.
69. Yamamoto, T.; Sugiyama, K.; Kushida, T.; Inoue, T.; Kanbara, T. J. Am. Chem. 1996, 118, 3930.
70. Brau, D.; Heeger, A. J. Appl. Phys. Lett. 1991, 58, 1982.
71. Burrows, P. E.; Shen, Z.; Bulovic, V.; McCarty, D. M.; Forrest, S. R.; Cronin, J. A.; Thompson, M. E. J. Appl. Phys. Lett. 1997, 79, 7991.
72. Optical Probes 2003 Congress, Venice 9-14 Feb 2003.