π-Conjugated donor-acceptor copolymers constituted of π-excessive and π-deficient arylene units. Optical and electrochemical properties in relation to CT structure of the polymer

Journal of the American Chemical Society

Volumn 118, Issue 43, 1996, Pages 10389-10399

  Yamamoto, Takakazu ^a   Zhou, Zhen Hua ^a   Kanbara, Takaki ^a   Shimura, Masaki ^a   Kizu, Kenichi ^a   Maruyama, Tsukasa ^a   Nakamura, Yoshiyuki ^a   Fukuda, Takashi ^a   Lee, Bang Lin ^a   Ooba, Naoki ^b   Tomaru, Satoru ^b   Kurihara, Takashi ^b   Kaino, Toshikuni ^b   Kubota, Kenji ^c   Sasaki, Shintaro ^d  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b NTT CORPORATION   (Japan)

^c GUNMA UNIVERSITY   (Japan)

^d JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMER; FURAN DERIVATIVE; PYRIDAZINE DERIVATIVE; PYRIDINE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG STRUCTURE; ELECTROCHEMISTRY;

EID: 0040206106     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961550t     Document Type: Article

References (83)

1. (a) Briegleb, G. Elektronen-Donator Acceptor-Komplexe; Springer: Berlin, 1961.
2. (b) Foster, F. Organic Charge-transfer Complexes; Academic Press: New York: 1969.
3. (a) Mulliken, R. S. J. Am. Chem. Soc. 1950, 72, 600.
4. (b) Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811.
5. E.g., (a) Priyadarshy, S.; Therien, M. J.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1504. (b) Maslak, P.; Chopra, A.; Moylan, C. R.; Wortmann, R.; Lebus, S.; Rheingold, A. L.; Yap, G. P. A. J. Am. Chem. Soc. 1996, 118, 1471. (c) Roest, M. R.; Verhoeven, J. W.; Schuddeboom, W.; Warman, J. M.; Lawson, J. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 1996, 118, 1762. (d) Bryan, C. D.; Cordes, A. W.; Goddard, J. D.; Haddon, R. C.; Hicks, R. G.; MacKinnon, C. D.; Mawhinney, R. C.; Oakley, R. T.; Palstra, T. T. M.; Perel, A. S. J. Am. Chem. Soc. 1996, 118, 330. (e) Fukuzumi, S. Adv. Electron Transf. Chem. 1992, 2, 67.
6. E.g., (a) Priyadarshy, S.; Therien, M. J.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1504. (b) Maslak, P.; Chopra, A.; Moylan, C. R.; Wortmann, R.; Lebus, S.; Rheingold, A. L.; Yap, G. P. A. J. Am. Chem. Soc. 1996, 118, 1471. (c) Roest, M. R.; Verhoeven, J. W.; Schuddeboom, W.; Warman, J. M.; Lawson, J. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 1996, 118, 1762. (d) Bryan, C. D.; Cordes, A. W.; Goddard, J. D.; Haddon, R. C.; Hicks, R. G.; MacKinnon, C. D.; Mawhinney, R. C.; Oakley, R. T.; Palstra, T. T. M.; Perel, A. S. J. Am. Chem. Soc. 1996, 118, 330. (e) Fukuzumi, S. Adv. Electron Transf. Chem. 1992, 2, 67.
7. E.g., (a) Priyadarshy, S.; Therien, M. J.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1504. (b) Maslak, P.; Chopra, A.; Moylan, C. R.; Wortmann, R.; Lebus, S.; Rheingold, A. L.; Yap, G. P. A. J. Am. Chem. Soc. 1996, 118, 1471. (c) Roest, M. R.; Verhoeven, J. W.; Schuddeboom, W.; Warman, J. M.; Lawson, J. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 1996, 118, 1762. (d) Bryan, C. D.; Cordes, A. W.; Goddard, J. D.; Haddon, R. C.; Hicks, R. G.; MacKinnon, C. D.; Mawhinney, R. C.; Oakley, R. T.; Palstra, T. T. M.; Perel, A. S. J. Am. Chem. Soc. 1996, 118, 330. (e) Fukuzumi, S. Adv. Electron Transf. Chem. 1992, 2, 67.
8. E.g., (a) Priyadarshy, S.; Therien, M. J.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1504. (b) Maslak, P.; Chopra, A.; Moylan, C. R.; Wortmann, R.; Lebus, S.; Rheingold, A. L.; Yap, G. P. A. J. Am. Chem. Soc. 1996, 118, 1471. (c) Roest, M. R.; Verhoeven, J. W.; Schuddeboom, W.; Warman, J. M.; Lawson, J. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 1996, 118, 1762. (d) Bryan, C. D.; Cordes, A. W.; Goddard, J. D.; Haddon, R. C.; Hicks, R. G.; MacKinnon, C. D.; Mawhinney, R. C.; Oakley, R. T.; Palstra, T. T. M.; Perel, A. S. J. Am. Chem. Soc. 1996, 118, 330. (e) Fukuzumi, S. Adv. Electron Transf. Chem. 1992, 2, 67.
9. E.g., (a) Priyadarshy, S.; Therien, M. J.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1504. (b) Maslak, P.; Chopra, A.; Moylan, C. R.; Wortmann, R.; Lebus, S.; Rheingold, A. L.; Yap, G. P. A. J. Am. Chem. Soc. 1996, 118, 1471. (c) Roest, M. R.; Verhoeven, J. W.; Schuddeboom, W.; Warman, J. M.; Lawson, J. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 1996, 118, 1762. (d) Bryan, C. D.; Cordes, A. W.; Goddard, J. D.; Haddon, R. C.; Hicks, R. G.; MacKinnon, C. D.; Mawhinney, R. C.; Oakley, R. T.; Palstra, T. T. M.; Perel, A. S. J. Am. Chem. Soc. 1996, 118, 330. (e) Fukuzumi, S. Adv. Electron Transf. Chem. 1992, 2, 67.
10. (a) Skotheim, T. A., Ed. Handbook of Conducting Polymers; Marcel Dekker: New York, 1986; Vols. I and II.
11. (b) Salaneck, W. R.; Clark, D. L.; Samuelsen, E. J. E. Science and Applications of Conducting Polymers; Adam Hilger: New York, 1990.
12. (c) MacDiarmid, A. G.; Heeger, A. J. NRL Memo. Rep. (Proc. Mol. Electron Devices Workshop) 1981 AD-A 05816,208.
13. (d) Bradley, D. D. C.; Mori, Y. In Electronic Properties of Conjugated Polymers III; Kuzmany, H., Mehring, M., Roth, S., Eds.; Springer: Berlin, 1989.
14. (a) Zhou, Z.-H.; Maruyama, T.; Kanbara, T.; Ikeda, T.; Ichimura, K.; Yamamoto, T.; Tokuda, K. J. Chem. Soc., Chem. Commun. 1991, 1210.
15. (b) Yamamoto, T.; Shimura, M.; Osakada, K.; Kubota, K. Chem. Lett. 1992, 1003.
16. (c) Kurihara, T.; Kaino, T.; Zhou, Z.-H.; Kanbara, T.; Yamamoto, T. Electron. Lett. 1992, 28, 681.
17. (d) Kanbara, T.; Miyazaki, Y.; Yamamoto, T. J. Polym. Sci. Part A: Polym. Chem. 1995, 33, 999.
18. (a) Havinga, E. E.; Ten Hoeve, W.; Wynberg, H. Polym. Bull. (Berlin) 1992, 29, 119.
19. (b) Ferraris, J. P.; Bravo, A.; Kim, W.; Hrncir, D. C. J. Chem. Soc., Chem. Commun. 1994, 991.
20. (c) Karikomi, M.; Kitamura, C.; Tanaka, S.; Yamashita, Y. J. Am. Chem. Soc. 1995, 117, 6791.
21. Newkome, G. R.; Paudler, W. W. Contemporary Heterocyclic Chemistry: John Wiley: New York, 1982.
22. (a) Lias, S. A.; Bartmess, J. E.; Holmes, J. L.; Levin, R. D.; Liebman, J. F.; Mallard, W. G. J. Phys. Chem. Ref. Data Suppl. 1988, 17, 1.
23. (b) Kagakubenran Kisohen; Jpn. Chem. Soc. Ed.; Maruzen: Tokyo; 1993, II-620 and 11-630.
24. (c) Distefano, G.; Pignatro, S.; Innorta, G.; Fringuelli, F.; Marioni, G.; Taticchi, A. Chem. Phys. Lett. 1973, 22, 132.
25. (d) Cooper, C. D.; Williamson, A. D.; Miller, J. C.; Compton, R. N. J. Chem. Phys. 1980, 73, 1527.
26. (e) Johnston, R. A. W.; Melon, F. A. J. Chem. Soc. Faraday Trans. 2 1973, 69, 1155.
27. (a) Jordan, K. D.; Burrow, P. D. Acc. Chem. Res. 1978, 11, 341.
28. (b) Jordan, K. D.; Burrow, P. D. Chem. Rev. 1987, 87, 557.
29. (c) Nenner, I.; Schulz, G. J. J. Chem. Phys. 1915, 62, 1747.
30. (d) Modelli, A.; Guerra, M.; Jones, D.; Distefano, G.; Irgolic, K. J., French, K.; Pappalardo, G. C. Chem. Phys. 1984, 88, 455.
31. Janousek, B. A.; Brauman, J. I. In Gas Phase Ion Chemistry; Ed. Bowers, M. T.; Academic Press: New York: 1979; Vol. 2, p 53.
32. Wiberg, K. B.; Lewis, T. P. J. Am. Chem. Soc. 1970, 92, 7154.
33. (a) Perichon, J.; Herlem, M.; Bobilliart, F.; Thiebault, A.; Nyberg, K. Encyclopedia of Electrochemistry of the Element; Bard, A. J., Lund, H., Eds.; Marcel Dekker: New York, 1978; Vol. XI, p 2.
34. (b) Baumgärtel, H.; Retzlav, K.-J. Ibid. 1984; Vol. XV, p 167.
35. (a) Yamamoto, T.; Maruyama, T.; Zhou, Z.-H.; Ito, T.; Fukuda, T.; Yoneda, Y.; Begum, F.; Ikeda, T.; Sasaki, S.; Takezoe, H.; Fukuda, A.; Kubota, K. J. Am. Chem. Soc. 1994, 116, 4832.
36. (b) Yamamoto, T.; Monta, Á.; Miyazaki, Y.; Maruyama, T.; Wakayama, H.; Zhou, Z.-H.; Nakamura, Y.; Kanbara, T.; Sasaki, S.; Kubota, K. Macromolecules 1992, 25, 1214.
37. (c) Yamamoto, T.; Sugiyama, K.; Kushida, T.; Inoue, T.; Kanbara, T. J. Am. Chem. Soc. 1996, 118, 3930.
38. (a) Zotti, G.; Schiavon, G.; Comisso, N.; Berlin, A.; Pagani, G. Synth. Met. 1990, 36, 337.
39. (b) Wernel, W.; Wegner, G. Makromol. Chem. 1987, 188, 1465.
40. (c) Yamamoto, T.; Wakayama, H.; Fukuda, T.; Kanbara, T. J. Phys. Chem. 1992, 96, 8677.
41. (d) Diaz, A. F.; Castillo, J. I.; Logan, J. A.; Lee, W.-Y. J. Electroanal. Chem. 1981, 129, 115.
42. (e) Dian, G.; Barbey, G.; Decroix, B. Synth. Met. 1986, 13, 281.
43. (f) Yoshino, K.; Kohno, Y.; Shiraishi, T.; Kaneto, K.; Inoue, S.; Tsukagoshi, K. Synth. Met. 1985, 10, 319.
44. (g) Yamamoto, T. J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 997.
45. (a) Wang, Y.; Quirk, R. P. Macromolecules 1995, 28, 3495.
46. (b) Kreyenschmidt, M.; Uckert, F.; Müllen, K. Macromolecules 1995, 28, 4577.
47. (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
48. (b) Bao, Z.; Chan, W.; Yu, L. Chem. Mater. 1993, 5, 2.
49. (a) Stothers, J. B. Carbon-13 NMR Spectroscopy; Academic Press: New York, 1972.
50. (b) Johnson, L. F.; Jankowski, W. C. Carbon-13 NMR Spectra; John Wiley: New York, 1972.
51. (a) Kubota, K.; Urabe, H.; Tominaga, Y.; Fujime, S. Macromolecules 1984, 17, 2096.
52. (b) Kubota, K.; Chu, B. Biopolymers 1983, 22, 1461.
53. v cf. ref 12a.
54. (a) Kovacic, P.; Feldman, M. B.; Kovacic, J. P.; Lando, J. B. J. Appl. Polym. Sci. 1968, 12, 1735.
55. (b) Froyer, G.; Maurice, F.; Mercier, J. P.; Riviere, D.I Le Cun, M.; Auvray, P. Polymer 1981, 22, 992.
56. (c) Sasaki, S.; Yamamoto, T.; Kanbara, T.; Morita, A.; Yamamoto, T. J. Polym. Sci. 1992, 30, 293.
57. (d) Mo, Z.; Lee, K.-B.; Moon, Y. B.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Macromolecules 1985, 18, 1972.
58. (e) Brückner, S.; Porzio, W. Makromol. Chem. 1988, 189, 961.
59. λmax at 410 nm.
60. λmax at 410 nm.
61. λmax at 410 nm.
62. Kanbara, T.; Yamamoto, T. Macromolecules 1993, 26, 3464.
63. 14f
64. Insertion of a less bulky five-membered ring unit like thiophene may release the steric repulsion in the homopolymer of quinoxaline to contribute to the red shift partly. However, as for pyridine copolymers, such an effect seems to be minor.
65. Glenis, S.; Benz, M.; LeGoff, E.; Schindler, J. L.; Kannewurf, C. R.; Kanatzidis, M. G. J. Am. Chem. Soc. 1993, 115, 12519.
66. Koffmann, T.; Beissner, G.; Mainbaum, R. Angew. Chem., Int. Ed. Engl, 1971, 10, 740.
67. (a) Torrance, J. B.; Vazquez, J. E.; Mayerle, J. J.; Lee, V. Y. Phys. Rev. Lett. 1981, 46, 253.
68. (b) Torrance, J. B.; Girlando, A.; Mayerle, J. J.; Crowley, J. I.: Lee, V. Y.; Batail, P. Ibid. 1981, 47, 1747.
69. Koshihara, S.; Tokura, Y. Kotaibutsuri 1992, 27, 367.
70. 14f shows a PL peak at 504 nm.
71. (a) Watkins, D. M.; Fox, M. A.; J. Am. Chem. Soc. 1994, 116, 6441.
72. (b) Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
73. (c) Goulle, V.; Harriman, A.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1034.
74. (d) Okamoto, Y.; Kido, J. Mater. Res. Soc. Symp. Proc. 1992, 277, 65.
75. The A-B couple (Figure 5b) is observable only after the potential is scanned at least once beyond -2.4 V to give the C-D couple.
76. E. g., (a) Hilman, A. R. Electrochemical Science and Technology of Polymers; Linford, R. G., Ed.; Elsevier: New York, 1987. (b) Anson, F. C.; Blauch, D. N.; Savéant, J.-M.; Shu, C.-F. J. Am. Chem. Soc. 1991, 113, 1922.
77. E. g., (a) Hilman, A. R. Electrochemical Science and Technology of Polymers; Linford, R. G., Ed.; Elsevier: New York, 1987. (b) Anson, F. C.; Blauch, D. N.; Savéant, J.-M.; Shu, C.-F. J. Am. Chem. Soc. 1991, 113, 1922.
78. Miyazaki, Y.; Yamamoto, T. Synth. Met. 1994, 64, 69.
79. (3) value than that measured at the mode adopted in the present study (supporting information).
80. (a) Guo, D.; Mazumdar, S.; Neher, D.; Stegeman, G. I.; Torruellas, W. In Organic Materials for Non-linear Optics III; Ashwell, G. J.; Bloor, D., Eds.; The Royal Society of Chemistry: Cambridge, 1993.
81. (b) Mori, Y.; Kurihara, T.; Kaino, T.; Tomaru, S. Jpn. J. Appl. Phys. 1992, 31, 896.
82. Gronowitz, S.; Frejd, T. Acta Chem. Scand. B 1976, 30, 313.
83. van Pham, C.; Macomber, R. S.; Mark, H. B., Jr.; Zimmer, H. J. Org. Chem. 1984, 49, 5250.