Synthesis, optical and electrochemical properties of arylenevinylene-based π-conjugated polymers with imidazolium units in the main chain

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 49, Issue 8, 2011, Pages 1895-1906

  Toba, Masaya ^a   Nakashima, Takuya ^a   Kawai, Tsuyoshi ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

conjugated polymers; copolymerization; electrochemistry; fluorescence

Indexed keywords

ARYL UNITS; ARYLENE; BLUE SHIFT; CATIONIC POLYMERS; CONJUGATION LENGTH; COUNTER ANIONS; ELECTRON-ACCEPTING; GAP ENERGY; HIGHEST OCCUPIED MOLECULAR ORBITAL; IMIDAZOLIUM; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MAIN CHAINS; METHYL GROUP; MODEL COMPOUND; NEGATIVE SHIFT; NEUTRAL MODEL; NEUTRAL MOLECULES; TWISTED CONFORMATION; UV-VIS AND FLUORESCENCE SPECTRA; VOLTAMMETRY MEASUREMENTS; X-RAY SINGLE-CRYSTAL ANALYSIS;

COPOLYMERIZATION; COPOLYMERS; CYCLIC VOLTAMMETRY; DYES; ELECTROCHEMICAL PROPERTIES; ELECTROCHEMISTRY; FLUORESCENCE; FUNCTIONAL GROUPS; MOLECULAR MODELING; MOLECULAR ORBITALS; NEGATIVE IONS; ORGANIC POLYMERS; SINGLE CRYSTALS;

CONJUGATED POLYMERS;

EID: 79952761623     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24618     Document Type: Article

References (61)

1. Burroughes, J. H.,;, Bradley, D. D. C.,;, Broen, A. R.,;, Marks, R. N.,;, Mackay, K.,;, Friend, R. H.,;, Burn, P. L.,;, Holmes, A. B., Nature 1990, 347, 539-541.
2. Greenham, N. C.,;, Moratti, S. C.,;, Bradley, D. D. C.,;, Friend, R. H.,;, Holmes, A. B., Nature 1993, 365, 628-630.
3. Kraft, A.,;, Grimsdale, A. C.,;, Holmes, A. B., Angew Chem Int Ed Engl 1998, 37, 402-428.
4. Perepichka, I. F.,;, Perepichka, D. F.,;, Meng, H.,;, Wudl, F., Adv Mater 2005, 17, 2281-2305.
5. Yang, R. Q.,;, Wu, H. B.,;, Cao, Y.,;, Bazan, G. C., J Am Chem Soc 2006, 128, 14422-14423.
6. Samuel, I. D. W.,;, Turnbull, G. A., Chem Rev 2007, 107, 1272-1295.
7. Yu, G.,;, Heerger, A., J Appl Phys 1995, 78, 4510-4515.
8. Tessler, N.,;, Denton, G. J.,;, Friend, R. H., Nature 1996, 382, 695-697.
9. Holmes, A. B., Nature 2003, 421, 800-801.
10. Lim, S. F.,;, Friend, R. H.,;, Rees, I. D.,;, Li, J.,;, Ma, Y. G.,;, Robinson, K.,;, Holmes, A. B.,;, Hennebicq, E.,;, Beljonne, D.,;, Cacialli, F., Adv Funct Mater 2005, 15, 981-988.
11. Zou, Y. P.,;, Wu, W. P.,;, Sang, G. Y.,;, Yang, Y.,;, Liu, Y. Q.,;, Li, Y. F., Macromolecules 2007, 40, 7231-7237.
12. McQuade, D. T.,;, Pullen, A. E.,;, Swager, T. M., Chem Rev 2000, 100, 2537-2574.
13. Rose, A.,;, Zhu, Z. G.,;, Madigan, C. F.,;, Swager, T. M.,;, Bulovic, V., Nature 2005, 434, 876-879.
14. Ho, H. A.,;, Bera-Aberem, M.,;, Leclerc, M., Chem-Eur J 2005, 11, 1718-1724.
15. Thomas, S. W.,;, Joly, G. D.,;, Swager, T. M., Chem Rev 2007, 107, 1339-1386.
16. Sugiyasu, K.,;, Swager, T. M., Bull Chem Soc Jpn 2007, 80, 2074-2083.
17. Patel, G. N.,;, Chance, R. R.,;, Witt, J. D., J Chem Phys 1979, 70, 4387-4392.
18. Kim, J.,;, Swager, T. M., Nature 2001, 411, 1030-1034.
19. James, P. V.,;, Sudeep, P. K.,;, Suresh, C. H.,;, Thomas, K. G., J Phys Chem A 2006, 110, 4329-4337.
20. Sudeep, P. K.,;, James, P. V.,;, Thomas, K. G.,;, Kamat, P. V., J Phys Chem A 2006, 110, 5642-5649.
21. Swager, T. M., Acc Chem Res 1998, 31, 201-207.
22. Bunz, U. H. F., Acc Chem Res 2001, 34, 998-1010.
23. Lu, L.,;, Jenekhe, S. A., Macromolecules 2001, 34, 6249-6254.
24. Jenekhe, S. A.,;, Lu, L. D.,;, Alam, M. M., Macromolecules 2001, 34, 7315-7322.
25. Goto, H.,;, Okamoto, Y.,;, Yashima, E., Macromolecules 2002, 35, 4590-4601.
26. Kawai, T.,;, Nakashima, Y.,;, Irie, M., Adv Mater 2005, 17, 309-314.
27. Sugiyasu, K.,;, Song, C.,;, Swager, T. M., Macromolecules 2006, 39, 5598-5600.
28. Hayasaka, H.,;, Tamura, K.,;, Akagi, K., Macromolecules 2008, 41, 2341-2346.
29. Sugiyasu, K.,;, Honsyo, Y.,;, Harrison, R. M.,;, Sato, M.,;, Yasuda, T.,;, Seki, S.,;, Takeuchi, M., J Am Chem Soc 2010, 132, 14754-14756.
30. Yamamoto, T.,;, Arai, M.,;, Kokubo, H.,;, Sasaki, S., Macromolecules 2003, 36, 7986-7993.
31. MacLean, B. J.,;, Pickup, P. G., J Mater Chem 2001, 11, 1357-1363.
32. Epstein, A. J.,;, Blatchford, J. W.,;, Wang, Y. Z.,;, Jessen, S. W.,;, Gebler, D. D.,;, Lin, L. B.,;, Gustafson, T. L.,;, Wang, H. L.,;, Park, Y. W.,;, Swager, T. M.,;, MacDiarmid, A. G., Synth Met 1996, 78, 253-261.
33. Blatchford, J. W.,;, Jassen, S. W.,;, Lin, L. B.,;, Gustafson, T. L.,;, Fu, D. K.,;, Wang, H. L.,;, Swager, T. M.,;, MacDiarmid, A. G.,;, Epstein, A., J Phys Rev B 1996, 54, 9180-9189.
34. Wang, C. S.,;, Kilitziraki, M.,;, MacBride, J. A. H.,;, Bryce, M. R.,;, Horsburgh, L. E.,;, Sheridan, A. K.,;, Monkman, A. P.,;, Samuel, I. D. W., Adv Mater 2000, 12, 217-222.
35. Monkman, A. P.,;, Palsson, L. O.,;, Higgins, R. W. T.,;, Wang, C. S.,;, Bryce, M. R.,;, Batsanov, A. S.,;, Howard, J. A. K., J Am Chem Soc 2002, 124, 6049-6055.
36. Yamamoto, T.,;, Sugiyama, K.,;, Kanbara, T.,;, Hayashi, H.,;, Etori, H., Macromol Chem Phys 1998, 199, 1807-1813.
37. Hayashi, H.,;, Yamamoto, T., Macromolecules 1998, 31, 6063-6070.
38. Ie, Y.,;, Kawabata, T.,;, Kaneda, T.,;, Aso, Y., Chem Lett 2006, 35, 1366-1367.
39. Curtis, M. D.,;, Cheng, H. T.,;, Johnson, J. A.,;, Nanos, J. I.,;, Kasim, R.,;, Elsenbaumer, R. L.,;, Ronda, L. G.,;, Martin, D. C., Chem Mater 1998, 10, 13-19.
40. Politis, J. K.,;, Curtis, M. D.,;, He, Y.,;, Kanicki, J., Macromolecules 1999, 32, 2484-2489.
41. Marsella, M. J.,;, Fu, D. K.,;, Swager, T. M., Adv Mater 1995, 7, 145-147.
42. Izuhara, D.,;, Swager, T. M., J Am Chem Soc 2009, 131, 17724-17725.
43. Fox, S. W., Chem Rev 1943, 32, 47-71.
44. Katritzky, A. R.,;, Karelson, M.,;, Sild, S.,;, Krygowski, T. M.,;, Jug, K., J Org Chem 1998, 63, 5228-5231.
45. Terashima, T.,;, Nakashima, T.,;, Kawai, T., Org Lett 2007, 9, 4195-4198.
46. Yamamoto, T.,;, Uemura, T.,;, Tanimoto, A.,;, Sasaki, S., Macromolecules 2003, 36, 1047-1053.
47. Kato, T., Science 2002, 295, 2414-2418.
48. Smiglak, M.,;, Metlen, A.,;, Rogers, R. D., Acc Chem Res 2007, 40, 1182-1192.
49. Kower, P. H. J.,;, Swager, T. M., J Am Chem Soc 2007, 129, 14042-14052.
50. Boydston, A. J.,;, Vu, P. D.,;, Dykhno, O. L.,;, Chang, V.,;, Wyatt, A. R.,;, Stockett, A. S.,;, Ritschdorff, E. T.,;, Shear, J. B.,;, Bielawski, C. W., J Am Chem Soc 2008, 130, 3143-3156.
51. Nakashima, T.,;, Goto, M.,;, Kawai, S.,;, Kawai, T., J Am Chem Soc 2008, 130, 14570-14575.
52. Nakashima, T.,;, Miyamura, K.,;, Sakai, T.,;, Kawai, T., Chem-Eur J 2009, 15, 1977-1984.
53. Wilkes, J. S.,;, Zaworotko, M. J., J Chem Soc Chem Commun 1992, 13, 965-967.
54. Ho, H. A.,;, Leclerc, M., J Am Chem Soc 2003, 125, 4412-4413.
55. Ho, H. A.,;, Boissinot, M.,;, Bergeron, M. G.,;, Corbeil, G.,;, Doré, K.,;, Boudreau, D.,;, Leclerc, M., Angew Chem Int Ed 2002, 41, 1548-1551.
56. Ho, H. A.,;, Doré, K.,;, Boissinot, M.,;, Bergeron, M. G.,;, Tanguay, R. M.,;, Boudreau, D.,;, Leclerc, M., J Am Chem Soc 2005, 127, 12637-12676.
57. Toba, M.,;, Nakashima, T.,;, Kawai, T., Macromolecules 2009, 42, 8068-8075.
58. Zheng, S.,;, Barlow, S.,;, Parker, T. C.,;, Marder, S. R., Tetrahedron Lett 2003, 44, 7989-7992.
59. Wen, S.,;, Pei, J.,;, Zhou, Y.,;, Li, P.,;, Xue, L.,;, Li,;, Yaowen X. B.,;, Tian, W., Macromolecules 2009, 42, 4977-4984.
60. Brédas, J. L.,;, Cornil, J.,;, Beljonne, D.,;, dos Santos, D. A.,;, Shuai, Z., Acc Chem Res 1999, 32, 267-276.
61. Liang, T. C.,;, Chiang, I. H.,;, Yang, P. J.,;, Kekuda, D.,;, Chu, C. W.,;, Lin, H. C., J Polym Sci Part A: Polym Chem 2009, 47, 5998-6013.