Small-Bandgap Conducting Polymers Based on Conjugated Poly(heteroarylene methines). 2. Synthesis, Structure, and Properties

Macromolecules

Volumn 28, Issue 2, 1995, Pages 465-480

  Chen, Wen Chang ^a   Jenekhe, Samson A ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARRIER CONCENTRATION; COMPUTATIONAL METHODS; DEHYDROGENATION; DOPING (ADDITIVES); ELECTRIC CONDUCTIVITY; ENERGY GAP; IODINE; ORGANIC CONDUCTORS; OXIDATION; SYNTHESIS (CHEMICAL); THIN FILMS;

POLY(HETEROARYLENE METHINES);

ORGANIC POLYMERS;

EID: 0029208638     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma00106a009     Document Type: Article

References (82)

1. Skotheim, T. A., Ed. Handbook of Conducting Polymers, Marcel Dekker: New York, 1986.
2. Bredas, J. L.; Chance, R. R., Eds. Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, Kluwer Academic Publishers: Dordrecht, Holland, 1990.
3. Bredas, J. L.; Sibley, R., Eds. Conjugated Polymers: The Novel Science and Technology of Highly Conducting and Nonlinear Optically Active Materials; Kluwer Academic Publishers: Dordrecht, Holland, 1991.
4. Kiess, H. G., Ed. Conjugated Conducting Polymers, Springer Series in Solid State Science; Springer-Verlag: Berlin, Heidelberg, 1992; Vol. 102.
5. Basescu, N.; Liu, Z.-X.; Moses, D.; Heeger, A. J.; Naarmann, H.; Theophilou, N. Nature 1987, 327, 403-405.
6. Jenekhe, S. A. Nature 1986, 322, 345-347.
7. Jenekhe, S. A. Macromolecules 1986, 19, 2663-2664.
8. Bredas, J. L.; Baughamn, R. H. J. Polym. Sci., Polym. Lett. Ed. 1983, 21, 475-479.
9. Bredas, J. L.; Themans, B.; Andre, J. L. J. Chem. Phys. 1983, 78, 6137-6148.
10. Bredas, J. L. Mol. Cryst. Liq. Cryst. 1985, 118, 49-56.
11. Bredas, J. L.; Heeger, A. J.; Wudl, F. J. Chem. Phys. 1986, 85, 4673-4678.
12. Hoogmartens, I.; Adriaensens, P.; Vanderzande, D.; Gelan, J.; Quattrocchi, C.; Lazzaroni, R.; Bredas, J. L. Macromolecules 1992, 25, 7347-7356.
13. Hong, S. Y.; Marynick, D. S. J. Chem. Phys. 1992, 96, 5497-5504.
14. Hong, S. Y.; Marynick, D. S. Macromolecules 1992, 25, 4652-4657.
15. Bredas, J. L.; Boudreaux, D. S.; Chance, R. R.; Sibley, R. Mol. Cryst. Liq. Cryst. 1985, 118, 323-326.
16. Boudreaux, D. S.; Chance, R. R.; Elsenbaumer, R. L.; Frommer, J. E.; Bredas, J. L.; Sibley, R. Phys. Rev. B 1985, 31, 652-655.
17. Lee, Y. S.; Kertesz, M. J. Chem. Phys. 1988, 88, 2609-2617.
18. Kertesz, M.; Lee, Y. S. J. Phys. Chem. 1987, 91, 2690-2692.
19. Lee, Y. S.; Kertesz, M.; Elsenbaumer, R. L. Chem. Mater. 1990, 2, 526-530.
20. Toussaint, J. M.; Themans, B.; Andre, J. M.; Bredas, J. L. Synth. Met. 1989, 28, C205-C210.
21. Pranata, J.; Marudarajan, V. S.; Dougherty, D. A. J. Am. Chem. Soc. 1989, 111, 2026-2030.
22. Tanaka, K.; Wang, S.; Yamabe, T. Synth. Met. 1989, 30, 57-65.
23. Tanaka, K.; Wang, S.; Yamabe, T. Synth. Met. 1990, 39, 225-231.
24. Otto, P.; Ladik, J. Synth. Met. 1990, 36, 327-335.
25. Toussaint, J. M.; Bredas, J. L. J. Chem. Phys. 1991, 94, 8122-8128.
26. Cui, C. X.; Kertesz, M. J. Am. Chem. Soc. 1991, 113, 4404-4409.
27. Toussaint, J. M.; Bredas, J. L. Synth. Met. 1992, 46, 325-335.
28. Agrawal, A. K.; Jenekhe, S. A., unpublished results.
29. Murakami, M.; Yoshimura, S. Mol. Cryst. Liq. Cryst. 1985, 118, 95-102.
30. Iqbal, Z.; Ivory, D. M.; Marti, J.; Bredas, J. L. Mol. Cryst. Liq. Cryst. 1985, 118, 103-110.
31. Kobayashi, M.; Colaneri, N.; Boysel, M.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717-5723.
32. Ikenoue, Y.; Wudl, F.; Heeger, A. J. Synth. Met. 1991, 40, 1-12.
33. Chandrasekhar, P.; Masulaitis, A. M.; Gumbs, R. W. Synth. Met. 1990, 36, 303-326.
34. Patil, A. O.; Wudl, F. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28 (2), 341-342.
35. Patil, A. O.; Wudl, F. Macromolecules 1988, 21, 540-542.
36. Moreno, V. P. A.; Rodero, A.; Fernandez, J. E. J. Org. Chem. 1982, 47, 3986-3987.
37. Fernandez, J. E.; Al-Jumah, K. Macromolecules 1984, 17, 2935-2937.
38. Al-Jumah, K.; Fernandez, J. E. Macromolecules 1987, 20, 1177-1180.
39. Braunling, H.; Jira, R. Synth. Met. 1987, 20, 375-378.
40. Jira, R.; Braunling, H. Synth. Met. 1987, 17, 691-696.
41. Becker, R.; Blochl, G.; Braunling, H. In ref lb, pp 133-139.
42. Wehrle, B.; Limbach, H.-H.; Braunling, H. Synth. Met. 1991, 39, 319-325.
43. Braunling, H.; Blochl, G.; Becker, R. Synth. Met. 1991, 41-43, 487-491.
44. Braunling, H.; Becker, R.; Blochl, G. Synth. Met. 1991, 41-43, 1539-1547.
45. Hanack, M.; Dewald, G. Synth. Met. 1989, 39, 409-414.
46. Hanack, M.; Hieber, G.; Dewald, G.; Ritter, H.; Rohrig, U. Polym. Mater. Sci. Eng. (Am. Chem. Soc., Div. Polym. Mater. Sci. Eng.) 1991, 64, 330-331.
47. Hanack, M.; Hieber, G.; Dewald, G.; Ritter, H. Synth. Met. 1991, 41-43, 507-511.
48. Hieber, G.; Hanack, M.; Wurst, K.; Strahle, J. Chem. Ber. 1991, 124, 1597-1605.
49. Talianni, C.; Zamboni, R.; Ruani, G.; Ostoia, P.; Bolognesi, A.; Catellani, M.; Destri, S.; Porzio, W. In Nonlinear Optical Effects in Organic Polymers; Messier, J., Kajzar, F., Prasad, P., Ulrich, D. R., Eds.; Kluwer Academic Publishers: Dordrecht, Holland, 1989; pp 159-172.
50. Lambert, T. L.; Ferraris, J. P. J. Chem. Soc., Chem. Commun. 1991, 752-754.
51. Ferraris, J. P.; Lambert, T. L. J. Chem. Soc., Chem. Commun. 1991, 1268-1270.
52. Kowalik, J.; Nguyen, H. T.; Tolbert, L. M. Synth. Met. 1991, 41-43, 435-438.
53. Kowalik, J.; Tolbert, L. M. Polym. Mater. Sci. Eng. 1991, 64, 214-215.
54. Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Polym. Bull. 1992, 29, 119-126.
55. Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153-195.
56. Becker, H.-D.; Turner, A. B. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1988; Vol. 2, pp 1351-1384.
57. Chen, W. C.; Jenekhe, S. A., in preparation.
58. Chen, W. C.; Jenekhe, S. A. Macromolecules 1995, 28, 454.
59. Jenekhe, S. A.; Lo, S. K.; Flom, S. R. Appl. Phys. Lett. 1989, 54, 2524-2526.
60. Jenekhe, S. A.; Chen, W. C.; Flom, S. R.; Lo, S. K. Appl. Phys. Lett. 1990, 57, 126-128.
61. Meth, J. S.; Vanherzeele, H.; Chen, W. C.; Jenekhe, S. A. Synth. Met. 1992, 49-50, 59-69.
62. Jenekhe, S. A. Macromolecules 1990, 23, 2848-2854.
63. CRC Handbook of Chemistry and Physics, 68th ed.; CRC Press: Boca Raton, FL, 1987; pp D151-D158.
64. Chance, R. R.; Boudreaux, D. S.; Bredas, J. L.; Sibley, R.ACS Symp. Ser. 1984, No. 242, 433-446.
65. Miller, L. L.; Nordbolm, G. D.; Mayeda, E. A. J. Org. Chem. 1972, 37, 916-918.
66. Sato, N.; Seki, K.; Inokuchi, H. J. Chem. Soc., Faraday Trans. 1981, 77, 1621-1633.
67. Leclerc, M.; Martinez, F.; Wegner, G. Makromol. Chem. 1989, 190, 3105-3116.
68. Daoust, G.; Leclerc, M. Macromolecules 1991, 24, 455-459.
69. Reid, D. H.; Fraser, M.; Molloy, B. B.; Payne, H. A.; Sutherland, R. G. Tetrahedron Lett. 1961, 530-535.
70. Macdonagh, A. F.; Plama, L. A. Biochem. J. 1980, 189, 193-208.
71. Chen, W. C.; Jenekhe, S. A. Macromolecules 1992, 25, 5919-5926.
72. Scott, J. C.; Pfluger, P.; Krounbi, M. T.; Street, G. B. Phys. Rev. B 1983, 28, 2140-2145.
73. Gourley, K. D.; Lillya, C. P.; Reynolds, J. R.; Chien, J. C. W. Macromolecules 1984, 17, 1025-1033.
74. Furukawa, Y.; Akimoto, M.; Harada, I. Synth. Met. 1987, 18, 151-156.
75. Roncali, J.; Garreau, R.; Yassar, A.; Marque, P.; Garnier, F.; Lemaire, M. J. Phys. Chem. 1987, 97, 6706-6714.
76. Yassar, A.; Roncali, J.; Garnier, F. Macromolecules 1989, 22, 804-809.
77. Eckhardt, H.; Shacklette, L. W.; Jen, K. Y.; Elsenbaumer, R. L. J. Chem. Phys. 1989, 91, 1303-1315.
78. Waltman, R. J.; Diaz, A. F.; Bargon, J. J. Electrochem. Soc. 1984, 131, 1452-1456.
79. Kittel, C. Introduction to Solid State Physics; Wiley: New York, 1986; Chapter 8.
80. Van Vlack, L. H. Elements of Materials Science and Engineering, 6th ed.; Addison-Wesley: Reading, MA, 1989; p 413.
81. Jen, K.-Y.; Miller, G. G.; Elsenbaumer, R. L. J. Chem. Soc., Chem. Commun. 1986, 1346-1347.
82. Hotta, S.; Soga, M.; Sonoda, N. Synth. Met. 1988, 26, 267-269.