Fluorocarbon-modified organic semiconductors: Molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties

Journal of the American Chemical Society

Volumn 128, Issue 17, 2006, Pages 5792-5801

  Yoon, Myung Han ^a   Facchetti, Antonio ^a   Stern, Charlotte E ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; FIELD EFFECT TRANSISTORS; FLUOROCARBONS; LIGHT ABSORPTION; MICROSTRUCTURE; OLIGOMERS; SINGLE CRYSTALS; THIN FILMS; X RAY DIFFRACTION;

ARENE(PERFLUOROARENE)-THIOPHENE; EMISSION PARAMETERS; MOLECULAR ARCHITECTURE; N-CHANNEL MOBILITY;

SEMICONDUCTING ORGANIC COMPOUNDS;

4,4' BIS[5 (2,2' DITHIOPHENYL)]PERFLUOROBIPHENYL; 4,4'BIS[5 (2,2' DITHIOPHENYL)]BIPHENYL; 5,5 DIPERFLUOROPHENYL 2,2':5',2'' TERTTHIOPHENE; 5,5 DIPERFLUOROPHENYLTHIOPHENE; 5,5' BIS[1 [4 (THIEN 2 YL)PERFLUOROPHENYL]] 2,2' DITHIOPHENE; 5,5' BIS[1 [4 (THIEN 2 YL)PHENYL]] 2,2' DITHIOPHENE; 5,5'' DIPERFLUOROPHENYL 2,2':5'',2''' QUATERTHIOPHENE; 5,5'' DIPERFLUOROPHENYL 2,2'DITHIOPHENE; 5,5'' DIPHENYL 2,2':5',2'':5'',2'' QUATERTHIOPHENE; FLUOROCARBON; OLIGOMER; POLYCYCLIC AROMATIC HYDROCARBON; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; ELECTROCHEMISTRY; FILM; FLUORESCENCE; FLUORINATION; LIGHT EMITTING DIODE; MELTING POINT; PHYSICAL CHEMISTRY; SCANNING ELECTRON MICROSCOPY; SEMICONDUCTOR; THERMOGRAVIMETRY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; FLUOROCARBONS; MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; POLYMERS; SEMICONDUCTORS;

EID: 33646540412     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060016a     Document Type: Article

References (104)

1. (a) Barbarella, G.; Melucci, M.; Sotgiu, G. Adv. Mater. 2005, 17, 1581.
2. (b) Printed Organic and Molecular Electronics; Gamota, D. R., Brazis, P., Kalyanasundaram, X., Zhang, J., Eds.; Kluwer Academic Publishers: New York, 2004.
3. (c) Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, Germany, 1999.
4. (d) Handbook of Conductive Polymers; Skotheim, T. A., Elsenbaumer R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; pp 325-326.
5. (e) Hotta, S. In Handbook of Organic Conductive Molecules and Polymers: Nalwa, H. S., Ed.; John Wiley & Sons: Chichester, U.K., 1997; Vol. 2, Chapter 8.
6. (e) Polythiophenes - Electrically Conductive Polymers; Schopf, G., Kossmehl, G., Eds.; Springer, Berlin, 1997.
7. (a) Hotta, S.; Lee, S. A. Synth. Met. 1999, 101, 551.
8. (b) Dingemans, T. J.; Bacher, C. J.; Thelakkat, M.; Pederson, L. G.; Samulski E. T.; Schimidt, H.-W. Synth. Met. 1999, 105, 171.
9. (a) Mohapatra, S.; Holmes, B. T.; Newman, C. R.; Prendergast, C. F.; Frisbie, C. D.; Ward, M. D. Adv. Funct. Mater. 2004, 14, 605.
10. (b) Yanagi, H.; Araki, Y.; Ohara, T.; Hotta, S.; Ichikawa M.; Taniguchi, Y. Adv. Funct. Mater. 2003, 13, 767.
11. (c) Casado, J.; Ruiz Delgado, M. C.; Shirota, Y.; Hernandez, V.; Lopez Navarrete, J. T. J. Phys. Chem. B 2003, 107, 2637.
12. (d) Ichikawa, M.; Yanagi, H.; Shimizu, Y.; Hotta, S.; Suganuma, N.; Koyama T.; Taniguchi, Y. Adv. Mater. 2002, 14, 1272.
13. (e) Apperloo, J. J.; Groenendaal, L. B.; Verheyen, H.; Jayakannan, M.; Janssen, R. A. J.; Dkhissi, A.; Beljonne, D.; Lazzaroni, R.; Bredas, J.-L. Chemistry 2002, 8, 2384.
14. (f) Moreno Castro, C.; Ruiz Delgado, M. C.; Hernandez, V.; Hotta, S.; Casado, J.; Lopez Navarrete, J. T. J. Phys. Chem. B 2002, 116, 10419.
15. (g) Lee, S. A.; Yoshida, Y.; Fukuyama M.; Hotta, S. Synth. Met. 1999, 106, 39.
16. (h) Videlot-Ackermann, C., Ackermann, J.; Ackermann, J.; Brisset, H.; Kawamura, K.; Yoshimoto, N.; Raynal, P.; El Kassmi, A.; Fages, F. J. Am Chem. Soc. 2005, 127, 16346.
17. (a) Hotta, S.; Katagiri, T. J. Heterocycl. Chem. 2003, 40, 845.
18. (b) Hotta S.; Kimura, H.; Lee, S. A.; Tamaki, T. J. Heterocycl. Chem. 2000, 37, 281.
19. (c) Hotta, S.; Lee, S. A.; Tamaki, T. J. Heterocycl. Chem. 2000, 37, 25.
20. (a) Yanagi, H.; Yoshiki, A.; Hotta, S.; Kobayashi, S. J. Appl. Phys. 2004, 96, 4240.
21. (b) Ichikawa, M.; Hibino, R.; Inoue, M.; Haritani, T.; Hotta, S.; Koyama, T.; Taniguchi, Y. Adv. Mater. 2003, 15, 213.
22. (c) Nagawa, M.; Hibino, R.; Hotta, S.; Yanagi, H.; Ichikawa, M.; Koyama, T.; Taniguchi. Y. Appl. Phys. Lett. 2002, 80, 544.
23. (d) Kim, Y. C.; Lee, T.-W.; Park, O.: Kim, C. Y.; Cho, H. N. Adv. Mater. 2001, 13, 646.
24. (a) Facchetti, A.; Letizia, J.; Yoon, M.-H.; Mushrush, M.; Katz, H. E.; Marks, T. J. Chem. Mater. 2004, 16, 4715.
25. (b) Katz, H. E.; Siegrist, T.; Lefenfeld, M.; Gopalan, P.; Mushrush, M.; Ocko, B.; Gang, O.; Jisrawl, N. J. Phys. Chem. B 2004, 108, 8567.
26. (c) Mushrush, M.; Facchetti, A.; Lefenfeld, M.; Katz, H. E.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 9414.
27. (d) Hong, X. M.; Katz, H. E.; Lovinger, A. J.; Wang, B.-C.; Raghavachari, K. Chem. Mater. 2001, 13, 4686.
28. (a) Meng, H.; Bendikov, M.; Mitchell, G.; Holgeson, R.; Wudl, F.; Bao, Z.; Siegrist, T.; Kloc, C.; Chen, C.-H. Adv. Mater. 2003, 15, 1090.
29. (b) Santato, C.; Manunza, I.; Bonfiglio, A.; Cicoira, F.; Cosseddu, P.; Zamboni, R.; Muccini, M. Appl. Phys. Lett. 2005, 86, 141106/1.
30. (c) Crouch, D. J.; Skabara, P. J.; Heeney, M.; McCulloch, I.; Coles, S. J.; Hursthouse, M. B. Chem. Commun. 2005, 1465.
31. (d) Li, D.; Borkent, E.-J.; Nortrup, R.; Moon, H.; Katz, H.; Bao, Z. Appl. Phys. Lett. 2005, 86, 042105/1.
32. (e) Rang, Z.; Nathan, M. I.; Ruden, P. P.; Podzorov, V.; Gershenson, M. E.; Newman, C. R.; Frisbie, C. D. Appl. Phys. Lett. 2005, 86, 123501/1.
33. (f) Tulevski, G. S.; Miao, Q.; Fukuto, M.; Abram, R.; Ocko, B.; Pindak, R.; Steigerwald, M. E.; Kagan, C. R.; Nuckolls, C. J. Am. Chem. Soc. 2004, 126, 15048.
34. (g) Sundar, V. C.; Zaumseil, J.; Podzorov, V.; Menard, E.; Willett, R. E.; Someya, T.; Gershenson, M. E., Rogers, J. A. Science 2004, 303, 1644.
35. (h) Gorjanc, T. C.; Levesque, I.; D'Iorio, M. Appl. Phys. Lett. 2004, 84, 930.
36. (i) Katz, H. E.; Kloc, C.; Sundar, V.; Zaumseil, J.; Briseno, A. E.; Bao, Z. J. Mater. Res. 2004, 19, 1995.
37. (j) Mohapatra, S.; Holmes, B. T.; Newman, C. R.; Prendergast, C. F.; Frisbie, C. D.; Ward, M. D. Adv. Funct. Mater. 2004, 14, 605.
38. (k) Morin, J.-F.; Drolet, N.; Tao, Y.; Leclerc, M. Chem. Mater. 2004, 16, 4619.
39. (l) Murphy, A. R.; Frechet, J. M. J.; Chang, P.; Lee, J.; Subramanian, V. J. Am. Chem. Soc. 2004, 126, 1596.
40. (m) Sheraw, C. D.; Jackson, T. N.; Eaton, D. E.; Anthony, J. E. Adv. Mater. 2003, 15, 2009.
41. (n) Meng, H.; Zheng, J.; Lovinger, A. J.; Wang, B.-C.; Van Patten, P. G.; Bao, Z. Chem. Mater. 2003, 15, 1778.
42. (o) Afzali, A.; Dimitrakopoulos, C. D.; Graham, T. O. Adv. Mater. 2003, 15, 2066.
43. (p) Locklin, J.; Li, D.; Mannsfeld, S. C. B.; Borkent, E.-J.; Meng, H.; Advincula, R.; Bao, Z. Chem. Mater. 2005, 17, 3366.
44. (q) Halik, M.; Klauk, H.; Zschieschang, U.; Scmid, G.; Ponomarenko, S.; Kiechmayer, S.; Weber, W. Adv. Mater. 2003, 15, 917.
45. (a) Yoon, M.-H.; DiBenedetto, S.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 1348.
46. (b) Facchetti, A.; Mushrush, M.; Yoon, M.-H.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13859.
47. (c) Facchetti, A.; Yoon, M.-H.; Stern, C. E.; Hutchison, G. R.; Ratner, M. J. Am. Chem. Soc. 2004, 126, 13480.
48. (d) Jones, B. A.; Ahrens, M. J.; Yoon, M.-H.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem., Int. Ed. 2004, 43, 6363.
49. (e) Facchetti, A.; Mushrush, M.; Katz, H. E.; Marks, T. J. Adv. Mater. 2003, 15, 33.
50. (f) Marks, T. J.; Facchetti, A. WO Patent 0 310 778, 2003.
51. (g) Facchetti, A.; Marks, T. J. Polym. Prepr. 2002, 43(1), 734.
52. (h) Marks, T. J.; Facchetti, A.; Sirringhaus, H.; Friend. R. H. WO Patent 0 209 201, 2002.
53. (i) Facchetti, A.; Deng, Y.; Wang, A.; Koide, Y.; Sirringhaus, H.; Marks, T. J.; Friend, R. H. Angew. Chem., Int. Ed. 2000, 39, 4547.
54. (a) Chua, L.-L.; Zaumseil, J.; Chang, J.-F.; Ou, E. C.-W.; Ho, P. K.-H.; Sirringhaus, H.; Friend, R. H. Nature 2005, 434, 194.
55. (b) Ando, S.; Nishida, J.; Tada, H.; Inoue, Y.; Tokito, S.; Yamashita, Y. J. Am. Chem. Soc. 2005, 127, 5336.
56. (c) Newman, C. R.; Frisbie, C. D.; da Silva Filho, D. A.; Bredas, J.-L.; Ewbank, P. C.; Mann, K. R. Chem. Mater. 2004, 16, 4436.
57. (d) Mitzi, D. B.; Kosbar, L. L.; Murray, C. E.; Copel, M.; Afzali, A Nature 2004, 428, 299.
58. (e) Sakamoto, Y.; Suzuki, T.; Kobayashi, M.; Gao, Y.; Fukai, Y.; Inoue, Y.; Sato, F.; Tokito, S. J. Am. Chem. Soc. 2004, 126, 8138.
59. (f) Kunugi, Y.; Takimiya, K.; Toyoshima, Y.; Yamashita, K.; Aso, Y.; Otsubo, T. J. Mater. Chem. 2004, 14, 1367.
60. (g) Chesterfield, R. J.; McKeen, J. C.; Newman, C. R.; Frisbie, C. D.; Ewbank, P. C.; Mann, K. R.; Miller, L. L. J. Appl. Phys. 2004, 95, 6396.
61. (h) Waldauf, C.; Schilinsky, P.; Perisutti, M.; Hauch, J.; Brabec, C. J. Adv. Mater. 2003, 15, 2084.
62. (i) Facchetti, A., Yoon, M.-H.; Stern, C. L.; Katz, H. E. Marks, T. J. Angew. Chem., Int. Ed. 2003, 42, 3900.
63. (j) Chesterfield, R. J.; Newman, C. R.; Pappenfus, T. M.; Ewbank, P. C.; Haukaas, M. H.; Mann, K. R.; Miller, L. L.; Frisbie, C. D. Adv. Mater. 2003, 15, 1278.
64. (k) Babel, A.; Janekhe, S. A. J. Am. Chem. Soc. 2003, 125, 13656.
65. (l) Shim, M.; Javey, A.; Kam, N. W. S.; Dai, H. J. Am. Chem. Soc. 2001, 123, 11512.
66. (m) Dodabalapur, A.; Lin, Y. Y.; Filas, R. W.; Bao, Z.; LaDuca, A.; Sarpeshkar, R.; Katz, H. E.; Li, W. Nature 2000, 403, 521.
67. Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Katz, H. E.; Marks, T. J. Angew. Chem., Int. Ed. 2003, 42, 3900.
68. March, J. In Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; Wiley: New York, 1992.
69. (a) Hotta, S.; Goto, M.; Azumi, R.; Inoue, M.; Ichikawa, M.; Taniguchi. Y. Chem. Mater. 2004, 16, 237.
70. (b) Nagawa, M.; Hibino, R.; Hotta, S.; Yanagi, H.; Ichikawa, M.; Koyama, T.; Taniguchi, Y. Appl. Phys. Lett. 2002, 80, 544.
71. All measurements were made on a CCD area detector instrument with graphite-monochromated Mo Kα (0.71073 Å) radiation. The data were collected at 153(2) K, and the structures were solved by direct methods and expanded using Fourier techniques. See Supporting Information for crystallographic details.
72. (a) Cho, D. M.; Parkin, S. R.; Watson, M. D. Org. Lett. 2005, 7, 1067.
73. (b) Crouch, D. J.; Skabara, P. J.; Heeney, M.; McCulloch, I.; Coles, S. J.; Hursthouse, M. B. Chem. Commun. 2005, 1465.
74. (c) Reichenbaecher, K.; Heike, S. I.; Juerg, H. Chem. Soc. Rev. 2005, 34, 22.
75. Fichou, D. J. Mater. Chem. 2000, 10, 571.
76. (a) McCullough, R. D. Adv. Mater. 1998, 10, 93.
77. (b) Brédas, J.-L. J. Chem. Phys. 1985, 82, 3809.
78. Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Harper Collins College Publishers: New York, 1993; p. 292.
79. Bertolucci, M. D.; Marsh, R. E. J. Appl. Cryst. 1974, 7, 87.
80. Gleason, W. B.; Britton, D. Cryst. Struct. Comm. 1976, 5, 483.
81. Dingemans, T. J.; Murthy, S. N.; Samulski, E. T. J. Phys. Chem. B 2001. 105, 8845.
82. (a) Garnier, F. Acc. Chem. Res. 1999, 32, 209.
83. (b) Yassar, A.; Horowitz, G.; Valat, P.; Wintgens, V.; Hmyene, M.; Deloffre, F.; Srivastava, P.; Lang, P.; Garnier, F. J. Phys. Chem. 1995, 99, 9155.
84. -5 M.
85. Yassar, A.; Horowitz, G.; Valat, P.; Wintgens, V.; Hmyene, M.; Deloffre, F.; Srivastava, P.; Lang, P.; Garnier, F. J. Phys. Chem. 1995, 99, 9155.
86. (a) Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH Publisher: New York, 1995.
87. (b) Pope, M.; Swenberg, C. E. In Electronic Processes in Organic Crystals and Polymers; Oxford University Press: Oxford, 1999.
88. (a) Jagur-Grodzinski, J. Polym. Adv. Technol. 2002, 13, 615-625.
89. (b) Cravino, A.; Sariciftci, N. S. J. Mater. Chem. 2002, 12, 1931.
90. (c) Wolf, M. O. Adv. Mater. 2001, 13, 545.
91. (d) Fabre, B.; Simonet, J. Coord. Chem. Rev. 1998, 178, 1211.
92. (e) Roncali, J. Chem. Rev. 1992, 92, 711.
93. (a) Domagala, W.; Laokowski, M.; Guillerez, S.; Bidan, G. Electrochim. Acta 2003, 48, 2379.
94. (b) Briehn, C. A.; Schiedel, M.-S.; Bonsen, E. M.; Schuhmann, W.; Bauerle, P. Angew. Chem., Int. Ed. 2001, 40, 4680.
95. (c) Nessakh, B.; Horowitz, G.; Gamier, F.; Deloffre, F.; Srivastava, P.; Yassar, A. J. Electroanal. Chem. 1995, 399, 97.
96. (d) Meerholz, K.; Heinze, J. Electrochim. Acta 1996, 41, 1839.
97. (a) Domagala, W.; Laokowski, M.; Guillerez, S.; Bidan, G. Electrochim. Acta 2003, 48, 2379.
98. (b) Jagur-Grodzinski, J. Polym. Adv. Technol. 2002, 13, 615.
99. (c) Meerholz, K.; Heinze, J. Electrochim. Acta 1996, 41, 1839.
100. Koh, S.; Facchetti, A.; Freeman, A. J.; Medevedeva, J.; Delley, L. D.; Ratner, M. A.; Marks, T. J. In preparation
101. Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99.
102. (a) Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 16866.
103. (b) Katz, H. E.; Torsi, L.; Dodabalapur, A. Chem. Mater. 1995, 7, 2235.
104. (c) Garnier, F.; Hajlaoui, R.; El Kassmi, A.; Horowitz, G.; Laigre, L.; Porzio, W.; Armanini, M.; Provasoli, F. Chem. Mater. 1998, 10, 3334.