Synthesis, photoluminescence, and electrochromism of polyamides containing (3,6-di-tert-butylcarbazol-9-yl)triphenylamine units

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 48, Issue 21, 2010, Pages 4775-4789

  Wang, Hui Min ^a   Hsiao, Sheng Huei ^a   Liou, Guey Sheng ^b   Sun, Chieh Hsiang ^c  

^a NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c TATUNG UNIVERSITY   (Taiwan)

Author keywords

carbazole; electrochemistry; electrochromism; fluorescence; polyamides; redox polymers; spectroelectrochemistry; triphenylamine

Indexed keywords

ACETONITRILE SOLUTIONS; AROMATIC DIAMINE; AROMATIC DICARBOXYLIC ACIDS; AROMATIC POLYAMIDES; CARBAZOLE; CARBAZOLE UNITS; COLORATION EFFICIENCIES; CYCLE STABILITY; ELECTROACTIVE; ELECTROACTIVE POLYMER FILMS; ELECTROCHROMICS; GLASS TRANSITION TEMPERATURE; HIGH THERMAL STABILITY; OPTICAL CONTRAST; POLYAMIDE FILMS; REDOX POLYMERS; REVERSIBLE REDOX COUPLES; SOLUTION-CAST; TRIPHENYL AMINES; WEIGHT LOSS TEMPERATURES;

ACETONITRILE; AMIDES; AMORPHOUS FILMS; AROMATIC COMPOUNDS; AROMATIZATION; CONDUCTING POLYMERS; ELECTROCHROMISM; ELECTROPOLYMERIZATION; FLUORESCENCE; GLASS TRANSITION; ORGANIC SOLVENTS; PHOSPHORYLATION; PLASTIC FILMS; POLYAMIDES; POLYCYCLIC AROMATIC HYDROCARBONS; POLYMERS; SPECTROELECTROCHEMISTRY;

POLYMER FILMS;

EID: 78649541352     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24269     Document Type: Article

References (93)

1. Monk, P. M. S.; Mortimer, R. J.; Rosseinsky, D. R., Electrochromism and Electrochromic Devices; Cambridge University Press: Cambridge, UK, 2007.
2. (a), Rosseinsky, D. R.; Montimer, R. J., Adv Mater 2001, 13, 783-793
3. (b), Michaelis, A.; Berneth, H.; Haarer, D.; Kostromine, S.; Neigl, R.; Schmidt, R., Adv Mater 2001, 13, 1825-1828
4. (c), Heuer, H. W.; Wehrmann, R.; Kirchmeyer, S., Adv Funct Mater 2002, 12, 89-94
5. (d), Sonmez, G.; Sonmez, H. B., J Mater Chem 2006, 16, 2473-2477
6. (e), Anderson, P.; Forchheimer, R.; Tehrani, P.; Berggren, M., Adv Funct Mater 2007, 17, 3074-3082
7. (f), Baetens, R.; Jelle, B. P.; Gustavsen, A., Sol Energy Mater Sol Cells 2010, 94, 87-105
8. (g), Beaupre, S.; Breton, A.-C.; Dumas, J.; Leclerc, M., Chem Mater 2009, 21, 1504-1513.
9. (a), Mortimer, R. J., Chem Soc Rev 1997, 26, 147-156
10. (b), Mortimer, R. J., Electrochim Acta 1999, 44, 2971-2981
11. (c), Rowley, N. M.; Mortimer, R. J., Sci Prog 2002, 85, 243-262
12. (d), Mortimer, R. J.; Dyer, A. L.; Reynolds, J. R., Displays 2006, 27, 2-18.
13. (a), Baeck, S.-H.; Choi, K.-S.; Jaramillo, T. F.; Stucky, G. D.; McFarland, E. W., Adv Mater 2003, 15, 1269-1273
14. (b), Lee, S.-H.; Deshpande, R.; Parilla, P. A.; Jones, K. M.; To, B.; Mahan, H.; Dillon, A. C., Adv Mater 2006, 18, 763-766
15. (c), Niklasson, G. A.; Granqvist, C. G., J Mater Chem 2007, 17, 127-156.
16. (a), Sonmez, G., Chem Commun 2005, 5251-5259
17. (b), Beaujuge, P. M.; Reynolds, J. R., Chem Rev 2010, 110, 268-320
18. (c), Patra, A.; Bendikov, M., J Mater Chem 2010, 20, 422-433.
19. (a), Welsh, D. M.; Kumar, A.; Morvant, M. C.; Reynolds, J. R., Synth Met 1999, 102, 967-968
20. (b), Groenendaal, L.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J. R., Adv Mater 2000, 12, 481-494
21. (c), Groenendaal, L.; Zotti, G.; Aubert, P.-H.; Waybright, S. M.; Reynolds, J. R., Adv Mater 2003, 15, 855-879
22. (d), Argun, A. A.; Aubert, P.-H.; Thompson, B. C.; Schwendeman, I.; Gaupp, C. L.; Hwang, J.; Pinto, N. J.; Tanner, D. B.; MacDiarmid, A. G.; Reynolds, J. R., Chem Mater 2004, 16, 4401-4412.
23. (a), Schottland, P.; Zong, K.; Gaupp, C. L.; Thompson, B. C.; Thomas, C. A.; Giurgiu, I.; Hickman, R.; Abboud, K. A.; Reynolds, J. R., Macromolecules 2000, 33, 7051-7061
24. (b), Zong, K.; Reynolds, J. R., J Org Chem 2001, 66, 6873-6882
25. (c), Sonmez, G.; Schwendeman, I.; Schottland, P.; Zong, K.; Reynolds, J. R., Macromolecules 2003, 36, 639-647
26. (d), Walczak, R. M.; Reynolds, J. R., Adv Mater 2006, 18, 1121-1131
27. (e), Walczak, R. M.; Jung, J.-H.; Cowart, J. S., Jr.; Reynolds, J. R., Macromolecules 2007, 40, 7777-7785.
28. (a), Sonmez, G.; Meng, H.; Wudl, F., Chem Mater 2004, 16, 574-580
29. (b), Sonmez, G.; Sonmez, H. B.; Shen, C. K. F.; Jost, B. W.; Rubin, Y.; Wudl, F., Macromolecules 2005, 38, 669-675
30. (c), Wu, C.-G.; Lu, M.-I.; Chang, S.-J.; Wei, C.-S., Adv Funct Mater 2007, 17, 1063-1070
31. (d), Durmus, A.; Gunbas, G. E.; Toppare, L., Chem Mater 2007, 19, 6247-6251
32. (e), Gunbas, G. E.; Durmas, A.; Toppare, L., Adv Mater 2008, 20, 691-695
33. (f), Gunbas, G. E.; Durmus, A.; Toppare, L., Adv Funct Mater 2008, 18, 2026-2030
34. (g), Balan, A.; Gunas, G.; Durmus, A.; Toppare, L., Chem Mater 2008, 20, 7510-7513
35. (h), Cihaner, A.; Algi, F., Adv Funct Mater 2008, 18, 3583-3589
36. (i), Pamuk, M.; Tirkes, S.; Cihaner, A.; Algi, F., Polymer 2010, 51, 62-68
37. (j), Icli, M.; Pamuk, M.; Algi, F.; Onal, A. M.; Cihaner, A., Chem Mater 2010, 22, 4034-4044
38. (k), Koyuncu, S.; Kus, M.; Demic, S.; Kaya, I.; Ozdemir, E.; Icli, S., J Polym Sci Part A: Polym Chem 2008, 46, 1974-1989
39. (l), Koyuncu, S.; Zafer, C.; Sefer, E.; Koyuncu, F. B.; Demic, S.; Kaya, I.; Ozdemir, E.; Icli, S., Synth Met 2009, 159, 2013-2021
40. (m), Is, O. D.; Koyuncu, F. B.; Koyuncu, S.; Ozdemir, E., Polymer 2010, 51, 1663-1669.
41. Yang, H. H., Kevlar Aramid Fiber; Wiley: Chichester, UK, 1993.
42. (a), Hsiao, S.-H.; Huang, T.-L., J Polym Sci Part A: Polym Chem 2002, 40, 947-957
43. (b), Liou, G.-S.; Hsiao, S.-H., J Polym Sci Part A: Polym Chem 2002, 40, 1781-1789
44. (c), Hsiao, S.-H.; Chang, Y.-M., J Polym Sci Part A: Polym Chem 2004, 42, 4056-4062
45. (d), San-Jose, N.; Gomez-Valdemoro, A.; Estevez, P.; Garcia, F. C.; Serna, F.; Garcia, J. M., Eur Polym J 2008, 44, 3578-3587
46. (e), Ghaemy, M.; Amini Nasab, S. M., React Funct Polym 2010, 70, 306-313
47. (f), Espeso, J. F.; Lozano, A. E.; de la Campa, J. G.; Garcia-Yoldi, I.; de Abajo, J., J Polym Sci Part A: Polym Chem 2010, 48, 1743-1751.
48. Garcia, J. M.; Garcia, F. C.; Serna, F. S.; de la Pena, J. L., Prog Polym Sci 2010, 35, 623-686 and the references cited herein.
49. (a), Thelakkat, M., Macromol Mater Eng 2002, 287, 442-461
50. (b), Shirota, Y.; Kageyama, H., Chem Rev 2007, 107, 953-1010.
51. (a), Liang, F.; Kurata, T.; Nishide, H.; Kido, J., J Polym Sci Part A: Polym Chem 2005, 43, 5765-5773
52. (b), Kim, Y.-H.; Zhao, Q.; Kwon, S.-K., J Polym Sci Part A: Polym Chem 2006, 44, 172-182
53. (c), Zhao, Q.; Kim, Y.-H.; Mai Dang, T. T.; Shin, D.-C.; You, H.; Kwon, S.-K., J Polym Sci Part A: Polym Chem 2007, 45, 341-347
54. (d), Chuang, C.-Y.; Shih, P.-I; Chien, C.-H.; Wu, F.-I.; Shu, C.-F., Macromolecules 2007, 40, 247-252
55. (e), Mikroyannidis, J. A.; Gibbons, K. M.; Kulkarni, A. P.; Jenekhe, S. A., Macromolecules 2008, 41, 663-674
56. (f), Park, J. H.; Huh, J. O.; Do, Y.; Lee, M. H., J Polym Sci Part A: Polym Chem 2008, 46, 5816-5825
57. (g), Park, J. H.; Yun, C.; Park, M. H.; Do, Y.; Yoo, S.; Lee, M. H., Macromolecules 2009, 42, 6840-6843
58. (h), Hsieh, B.-Y.; Chen, Y., J Polym Sci Part A: Polym Chem 2009, 47, 1553-1566
59. (i), Nursalim, G.; Chen, Y., Polymer 2010, 51, 3187-3195.
60. (a), Leung, M.-k.; Chou, M.-Y.; Su, Y. O.; Chiang, C. L.; Chen, H.-L.; Yang, C. F.; Yang, C.-C.; Lin, C.-C.; Chen, H.-T., Org Lett 2003, 5, 839-842
61. (b), Beaupre, S.; Dumas, J.; Leclerc, M., Chem Mater 2006, 18, 4011-4018
62. (c), Otero, L.; Sereno, L.; Fungo, F.; Liao, Y.-L.; Lin, C.-Y.; Wong, K.-T., Chem Mater 2006, 18, 3495-3502
63. (d), Natera, J.; Otero, L.; Sereno, L.; Fungo, F.; Wang, N.-S.; Tsai, Y.-M.; Hwu, T.-Y.; Wong, K.-T., Macromolecules 2007, 40, 4456-4463.
64. (a), Cheng, S.-H.; Hsiao, S.-H.; Su, T.-H.; Liou, G.-S., Macromolecules 2005, 38, 307-316
65. (b), Hsiao, S.-H.; Chang, Y.-M.; Chen, H.-W.; Liou, G.-S., J Polym Sci Part A: Polym Chem 2006, 44, 4579-4592
66. (c), Liou, G.-S.; Hsiao, S.-H.; Huang, N.-K.; Yang, Y.-L., Macromolecules 2006, 39, 5337-5346
67. (d), Chang, C.-W.; Liou, G.-S.; Hsiao, S.-H., J Mater Chem 2007, 17, 1007-1015
68. (e), Hsiao, S.-H.; Liou, G.-S.; Kung, Y.-C.; Yen, H.-J., Macromolecules 2008, 41, 2800-2808
69. (f), Kung, Y.-C.; Liou, G.-S.; Hsiao, S.-H., J Polym Sci Part A: Polym Chem 2009, 47, 1740-1755
70. (g), Hsiao, S.-H.; Liou, G.-S.; Wang, H.-M., J Polym Sci Part A: Polym Chem 2009, 47, 2330-2343
71. (h), Hsiao, S.-H.; Liou, G.-S.; Kung, Y.-C.; Chang, Y.-M., J Polym Sci Part A: Polym Chem 2010, 48, 2798-2809.
72. (a), Chen, J. P.; Natansohn, A., Macromolecules 1999, 32, 3171-3177
73. (b), Morin, J.-F.; Leclerc, M.; Ades, D.; Siove, A., Macromol Rapid Commun 2005, 26, 761-778.
74. (a), Grazulevicius, J. V.; Strohriegl, P.; Pielichowski, J.; Pielichowski, K., Prog Polym Sci 2003, 28, 1297-1353
75. (b), Blouin, N.; Leclerc, M., Acc Chem Res 2008, 41, 1110-1119
76. (c), Boudreault, P.-L. T.; Beaupre, S.; Leclerc, M., Polym Chem 2010, 1, 127-136.
77. Tsai, M.-H.; Lin, H.-W.; Su, H.-C.; Ke, T.-H.; Wu, C.-C.; Fang, F.-C.; Liao, Y.-L.; Wong, K.-T.; Wu, C.-I., Adv Mater 2006, 18, 1216-1220.
78. Yang, C.-P.; Chen, R.-S.; Chen, K.-H., Colloid Polym Sci 2003, 281, 505-515.
79. Schaerlaekens, M.; Hendrickx, E.; Hameurlaine, A.; Dehaen, W.; Persoons, A., Chem Phys 2002, 277, 43-52.
80. Demas, J. N.; Crosby, G. A., J Phys Chem 1971, 75, 991-1024.
81. Zhu, Z.; Moore, J. S., J Org Chem 2000, 65, 116-123.
82. Chen, Y.-C.; Huang, G.-S.; Hsiao, C.-C.; Chen, S.-A., J Am Chem Soc 2006, 128, 8549-8558.
83. (a), Yamazaki, N.; Higashi, F.; Kawabata, J., J Polym Chem Polym Chem Ed 1974, 12, 2149-2155
84. (b), Yamazaki, N.; Matsumoto, M.; Higashi, F., J Polym Sci Polym Chem Ed 1975, 13, 1373-1380.
85. A detailed description of the synthesis of 4,4′-diamino-4″- (3,6-di-tert-butylcarbazol-9-yl)TPA (diamine 6f) and its based polyamides and polyimides is at hand and will be published in the near future: Liao, S.-H., Dissertation, Tatung University, Taiwan, 2007.
86. (a), Ambrose, J. F.; Nelson, R. F., J Electrochem Soc 1968, 115, 1159-1164
87. (b), Ambrose, J. F.; Capenter, L. L.; Nelson, R. F., J Electrochem Soc 1975, 122, 876-894.
88. Shen, J.-Y.; Lee, C.-Y.; Huang, T.-H.; Lin, J.-T.; Tao, Y.-T.; Chien, C.-H.; Tsai, C., J Mater Chem 2005, 15, 2455-2463.
89. (a), Lambert, C.; Noll, G., J Am Chem Soc 1999, 121, 8434-8442
90. (b), Lambert, C.; Noll, G., Angew Chem Int Ed 1998, 37, 2107-2110
91. (c), Lambert, C.; Noll, G., Synth Met 2003, 139, 57-62
92. (d), Chou, M.-Y.; Leung, M.-k.; Su, Y. O.; Chiang, C. L.; Lin, C.-C.; Liu, J.-H.; Kuo, C.-K.; Mou, C.-Y., Chem Mater 2004, 16, 654-661
93. (e), Chiang, C. C.; Chen, H.-C.; Lee, C.-S.; Leung, M.-k.; Lin, K.-R.; Hsieh, K.-H., Chem Mater 2008, 20, 540-552.