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N- and P-Type Building Blocks for Organic Electronics Based on Oligothiophene Cores

  • Antonio Facchetti (a1), Myung-Han Yoon (a2), Howard E. Katz (a2), Melissa Mushrush (a2) and Tobin J. Marks (a1)...

Abstract

Organic semiconductors exhibiting complementary-type carrier mobility are the key components for the development of the field of “plastic electronics”. We present here a novel series of αω- and isomerically pure β,β'-diperfluorohexyl-substituted thiophene and study the impact of fluoroalkyl substitution and conjugation length vìs-à-vìs the corresponding fluorinefree analogues. Trends between the fluorinated and fluorine-free families in molecular packing, HOMO-LUMO gap, and π-π interactions are found to be strikingly similar. TFT measurements indicate that all members of the fluorinated series are n-type semiconductors

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[1] (a) Pappenfus, T. M., Chesterfield, R. J., Frisbie, C., Daniel, M., Kent, R. Casado, J., Raff, J. D., Miller, L. L., J. Am. Chem. Soc. 124, 4184, (2002). (b) P. R. L. Malenfant, C. D. Dimitrakopoulos, J. D. Gelorme, L. L. Kosbar, T. O. Graham, A. Curioni, W. Andreoni, Appl. Phys. Lett. 80, 2517, (2002). (c) H. E. Katz, J. Johnson, A. J. Lovinger, W. Li, J. Am. Chem. Soc. 122, 7787, (2000). (d) B. Crone, A. Dodabalapur, Y. Y. Lin, R. W. Filas, Z. Bao, A. LaDuca, R. Sarpeshkar, H. E. Katz, W. Li, Nature 403, 521, (2000). (e) S. B. Heidenhain, Y. Sakamoto, T. Suzuki, A. Miura, H. Fujikawa, T., Mori, S. Tokito, Y. Taga, J. Am. Chem. Soc 122, 10240, (2000).
[2] (a)Pope, M., Swenberg, C. E., in Electronic Processes in Organic Crystals and Polymers, Oxford University Press, Oxford 1999. (b) C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 14, 99, (2002).
[3] (a) Facchetti, A., Mushrush, M., Katz, H. E., Marks, T. J., Adv. Mater. 15, 33, (2003). (b) A. Facchetti, Y. Deng, A. Wang, Y. Koide, H. Sirringhaus, T. J. Marks, R. H. Friend, Angew. Chem. Int. Ed. 39, 4547, (2000).
[4] For TFT performance. DH-4T: Garnier, F., Hajlaoui, R., ElKassmi, A., Horowitz, G., Laigre, L., Porzio, W., Armanini, M., Provasoli, F., Chem. Mater. 10, 3334, 1998. DH-5T: W. Li, H. E. Katz, A. J. Lovinger, J. G. Laquindanum, Chem. Mat. 11, 458, 1999. DH-6T: C. 0D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 14, 99, 2002.

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