Supramolecular ordering, thermal behavior, and photophysical, electrochemical, and electroluminescent properties of alkoxy-substituted yne-containing poly(phenylene-vinylene)s

Macromolecules

Volumn 37, Issue 20, 2004, Pages 7451-7463

  Egbe, Daniel Ayuk Mbi ^a   Carbonnier, Benjamin ^b   Ding, Liming ^c   Mühlbacher, David ^d   Birckner, Eckhard ^a   Pakula, Tadeusz ^b   Karasz, Frank E ^c   Grummt, Ulrich Walter ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^c UNIVERSITY OF MASSACHUSETTS   (United States)

^d Konarka Austria Forschungs u   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMICAL CELLS; INTERMOLECULAR INTERACTIONS; SUPRAMOLECULAR INTERACTIONS; THERMAL BEHAVIOR;

CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTROLUMINESCENCE; FIELD EFFECT TRANSISTORS; FLUORESCENCE; LIGHT EMITTING DIODES; NUCLEATION; OLEFINS; PHOTOLUMINESCENCE; SELF ASSEMBLY; STACKING FAULTS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

ORGANIC POLYMERS;

EID: 6344294417     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0488111     Document Type: Article

References (82)

1. (a) Hadziioannou, G., van Hutten, P. F., Eds. Semiconducting Polymers: Chemistry, Physics and Engineering, 1st ed.; Wiley-VCH: Weinheim, Germany, 2000.
2. (b) Denton, F. R.; Lahti, P. M. In Electrical and Optical Polymers; Wise, D. L., Wnek, G. E., Trantolo, D. J., Cooper, T. M., Gresser, J. D., Eds.; Marcel Dekker: New York, 1998; p 61.
3. (a) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402.
4. (b) Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, T. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Brédas, J. L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 397, 121.
5. (c) Schmitz, C.; Pösch, P.; Thelakkat, M.; Schmidt, H.-W.; Montali, A.; Feldman, K.; Smith, P.; Weder, C. Adv. Funct. Mater. 2001, 11,41.
6. (d) Pschirer, N. G.; Miteva, T.; Evans, U.; Roberts, R. S.; Marshall, A. R.; Neher, D.; Myrick, M. L.; Bunz, U. H. F. Adv. Mater. 2001, 13, 2691.
7. (e) Sarker, A. M.; Gürel, E. E.; Ding, L.; Styche, E.; Lahti, P. M.; Karasz, F. E. Synth. Met. 2002, 132 (3), 227.
8. Pel, Q.; Yu, G.; Zhang, C.; Yang, Y.; Heeger, A. J. Science 1995, 269, 1086.
9. Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359.
10. (a) Pauck, T.; Hernnig, R.; Perner, M.; Lemmer, U.; Siegner, U.; Mahrt, R. F.; Scherf, U.; Müllen, K.; Bässler, E. O.; Göbel, E. O. Chem. Phys. Lett. 1995, 244, 171.
11. (b) Hide, F.; Diaz-Garcia, M. A.; Schwartz, B. J.; Andersson, M. R.; Pei, Q.; Heeger, A. J. Science 1996, 273, 1833.
12. (a) Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15.
13. (b) Piok, T.; Brands, C.; Neyman, P. J.; Erlacher, A.; Soman, C.; Murray, M. A.; Schroeder, R.; Graupner, W.; Heflin, J. R.; Drake, A.; Miller, M. B.; Wang, H.; Gibson, H.; Dorn, H. C.; Leising, G.; Guzy, M.; Davis, R. M. Synth. Met. 2001, 116, 343.
14. Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. J., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998.
15. Bunz, U. H. F. Chem. Rev. 2000, 100, 1605.
16. (a) Brizius, G.; Pschirer, N. G.; Steffen, W.; Stitzer, K.; zur Loye, H.-C.; Bunz, U. H. F. J. Am. Chem. Soc. 2000, 122, 12435.
17. (b) Bunz, U. H. F. Acc. Chem. Res. 2001, 34, 998.
18. (c) Ramos, A. M.; Rispens, M. T.; van Duren, J. K. J.; Hummelen, J. C.; Janssen, R. A. J. J. Am. Chem. Soc. 2001,123, 6714.
19. (d) Schenning, A. P. H.; Tsipis, A. C.; Meskers, S. C. J.; Beljonne, D.; Meijer, E. W.; Brédas, J. L. Chem. Mater. 2002, 14, 1362.
20. (e) Wilson, J. N.; Windscheif, P. M.; Evans, U.; Myrick, M. L.; Bunz, U. H. F. Macromolecules 2002, 35, 8681.
21. (f) Chu, Q.; Pang, Y.; Ding, L.; Karasz, F. E. Macromolecules 2003,36, 3848.
22. (g) Tong, M.; Sheng, C. X.; Yang, C.; Vardeny, Z. V. Phys. Rev. B 2004, 69, 155211.
23. (a) Egbe, D. A. M.; Tillmann, H.; Birckner, E.; Klemm, E. Macromol. Chem. Phys. 2001, 202, 2712.
24. (b) Egbe, D. A. M.; Roll, C. P.; Birckner, E.; Grummt, U.-W.; Stockmann, R.; Klemm, E. Macromolecules 2002, 35, 3825.
25. (c) Egbe, D. A. M.; Birckner, E.; Klemm, E. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2670.
26. (d) Egbe, D. A. M.; Bader, C.; Nowotny, J.; Günther, W.; Klemm, E. Macromolecules 2003, 36, 5459.
27. (e) Egbe, D. A. M.; Bader, C.; Klemm, E.; Ding, L.; Karasz, F. E.; Grummt, U.-W.; Birckner, E. Macromolecules 2003, 36, 9303.
28. (f) Zhokhavets, U.; Goldhahn, R.; Gobsch, G.; Al-Ibrahim, M.; Roth, H.-K.; Sensfuss, S.; Klemm, E.; Egbe, D. A. M. Thin Solid Films 2003, 444, 215.
29. (g) Egbe, D. A. M.; Stockmann, R.; Hotzel, M. J. Opt. A: Pure Appl. Opt. 2004, 6, 791.
30. Bucknall, D. G.; Andersen, H. L. Science 2003, 302, 1904.
31. Cacialli, F.; Samori, P.; Silva, C. Mater. Today 2004, 4, 24.
32. (a) Levitsky, I. A.; Kim, J.; Swager, T. M. Macromolecules 2001, 34, 2315.
33. (b) Perahia, D.; Traiphol, R.; Bunz, U. H. F. Macromolecules 2001, 34, 151.
34. (c) Weder, C.; Wrighton, M. S.; Spreiter, R.; Bosshard, C.; Günter, P. J. Phys. Chem. 1996, 100, 18931.
35. Meier, H.; Aust, H. J. Prakt. Chem. 1999, 341, 466.
36. Pfeiffer, S.; Hörhold, H.-H. Macromol. Chem. Phys. 1999, 200, 1870.
37. (a) Ballauff, M. Makromol. Chem., Rapid Commun. 1986, 7, 407.
38. (b) Rodriguez-Parada, J. M.; Duran, R.; Wegner, G. Macromolecules 1989, 22, 2507.
39. (a) Majnusz, J.; Catala, J. M.; Lenz, R. W. Eur. Polym. J. 1983, 19, 1043.
40. (b) Krigbaum, W. R.; Hakemi, H.; Kotek, R. Macromolecules 1985, 18, 965.
41. (a) Stein, R. S.; Rhodes, M. B. J. Appl. Phys. 1960, 31, 1873.
42. (b) Stein, R. S. Structures and Properties of Polymer Films, Lenz, R. W., Stein, R. S., Eds.; Plenum: New York, 1973
43. (c) Samuels, R. J. J. Polym. Sci., Part A-2, 1971, 9, 2165.
44. (a) Stein, R. S.; Erhardt, P.; van Aartsen, J. J.; Clough, S.; Rhodes, M. J. Polym. Sci., Part C 1966, 13, 1.
45. Andreopoulou, A. K.; Carbonnier, B.; Kallitsis, J. K.; Pakula, T. Macromolecules 2004, 37, 3576.
46. (a) Swan, P. R. J. Polym. Sci. 1962, 56, 403.
47. (b) Jordan, E. F.; Feideisen, D. W.; Wrigley, A. N. J. Polym. Sci., Part A-1 1971, 9, 1835.
48. (c) Hsieh, H. W.; Post, B.; Morawetz, H. J. Polym. Sci., Polym. Phys. Ed. 1976, 14, 1241.
49. (a) Winokur, M. J.; Wamsley, P.; Moulton, J.; Smith, P.; Heeger, A. J. Macromolecules 1991, 24, 3812.
50. (b) McCullough, R. D.; Tristram-Nagle, S.; Williams, S. P.; Loewe, R. D.; Jayaraman, M. J. Am. Chem. Soc. 1993, 115, 4910.
51. (c) McCullough, R. D.; Ewbank, P. C.; Loewe, R. S. J. Am. Chem. Soc. 1997, 119, 633.
52. (a) Chen, T.-A.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087.
53. (b) Wu, X.; Chen, T.-A.; Rieke, R. D. Macromolecules 1995, 28, 2101.
54. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233.
55. (a) Yamamoto, T. Chem. Lett. 1996, 703.
56. (b) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B.-L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.; Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047.
57. (c) Yamamoto, T.; Suganuma, H.; Maruyama, T.; Inoue, T.; Muramatsu, Y.; Arai, M.; Komarudin, D.; Ooba, N.; Tomaru, S.; Sasaki, S.; Kubota, K. Chem. Mater. 1997, 9, 1217.
58. (d) Yamamoto, T.; Oguro, D. Macromolecules 1996, 29, 1833.
59. (e) Morikita, T.; Yamaguchi, I.; Yamamoto, T. Adv. Mater. 2001, 13, 1862
60. (f) Yamamoto, T.; Lee, B.-L. Macromolecules 2002, 35, 2993.
61. (a) Ballauf, M.; Schmidt, G. F. Mol. Cryst. Liq. Cryst. 1987, 147, 163.
62. (b) Ballauf, M.; Schmidt, G. F. Makromol. Chem., Rapid. Commun. 1987, 8, 93.
63. (c) Watanabe, J.; Harkness, B. R.; Sone, M. Polym. J. 1992, 24, 1119.
64. (d) Kloppenburg, L.; Jones, D.; Claridge, J. B.; zur Loye, H.-C.; Bunz, U. H. F. Macromolecules 1999, 32, 4460.
65. Law, K.-Y. in Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; John Wiley & Sons Ltd.: West Sussex 1997; Vol. 1. p 487.
66. Funahashi, M.; Hanna, J. I. Phys. Rev. Lett. 1997, 78, 2184.
67. Kim,.S.; Park, S. Y. Macromolecules 2001, 34, 3947.
68. You, W.; Cao, S.; Hou, Z.; Yu, L. Macromolecules 2003, 36, 7014.
69. Strickler, S. J.; Berg, R. A. J. Chem. Phys. 1962, 37, 814.
70. The fully optimized geometry was obtained from density functional theory calculations using b31yp/6-31 g(d) functional implemented in the GAUSSIAN98 package [Frisch, M. J.; et al. Gaussian98 (revision A7), Gaussian Inc.: Pittsburgh, PA, 1989], The barriers are giving the differences between the total energies of the coplanar and 90̈twisted conformations, that means, they do not contain thermal and zero-point energy corrections.
71. (a) Kaufmann, J. H.; Chung, T.-C.; Heeger, A. J. J. Electrochem. Soc. 1984, 131, 2847.
72. (b) Eckhardt, H.; Shacklette, L. W.; Yen, K. Y.; Elsenbaumer, R. L. J. Chem. Phys. 1989, 91, 1303.
73. (c) Mühlbacher, D.; Neugebauer, H.; Cravino, A.; Sariciftci, N. S.; van Duren, J. K. J.; Dhanabalan, A.; van Hal, P. A.; Janssen, R. A. J.; Hummelen, J. C. Mol. Cryst. Liq. Cryst. 2002, 385, 205.
74. (d) Mühlbacher, D.; Cravino, A.; Neugebauer, H.; Sariciftci, N. S. Synth. Met. 2003, 137, 1361.
75. (e) Mühlbacher, D. Diploma thesis on Comparative Study of the Electrochemical and Optical Band Gap of Organic Semiconductors. Johann Kepler University, Linz, Austria, 2002.
76. Liu, B.; Yu, W.-L.; Lai, Y.-H.; Huang, W. Chem. Mater. 2001, 13, 1984.
77. (a) Gomer, R. J.; Tryson, G. J. Chem. Phys. 1977, 66, 4413.
78. (b) Kötz, R.; Neff, H.; Müller, K. J. Electroanal. Chem. 1986, 215, 331.
79. (a) Braun, D.; Heeger, A. J. Appl. Phys. Lett. 1991, 58, 1982.
80. (b) Braun, D.; Mosea, D.; Zhang, C.; Heeger, A. J. Appl. Phys. Lett. 1992, 61, 3092.
81. Ding, L.; Egbe, D. A. M.; Karasz, F. E. Macromolecules 2004, 37, 6124.
82. Sensfuss, S.; Al-Ibrahim, M.; Konkin, A.; Nazmutdinova, G.; Zhokhavets, U.; Gobsch, G.; Egbe, D. A. M.; Klemm, E.; Roth, H.-K. Proc. SPIE 2004, 5125, 129.