A molecular tool box is presented, allowing the efficient synthesis of a broad variety of bis(tetracenyl) aromatics. These materials might be of considerable interest as semiconductors in organic field-effect transistors. The general synthetic strategy applied here involves Diels-Alder reactions of bromobenzocyclobutene derivatives and arene-1,4-endoxides, followed by transition-metal catalyzed condensation reactions of the formed 9-bromo-6,11-dihydrotetracene derivatives with aryldiboronic and -stannyl derivatives, respectively. In the final step, the resulting bis(dihydrotetracenyl) derivatives were dehydrogenated, giving the bis(tetracenyl) aromatics in good yields. They were characterized using NMR, UV-vis and mass spectrometry. Moreover, for some of these semiconductors the charge carrier mobility in thin film transistors has been determined.
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J. Luo, H. Hart, J. Org. Chem. 52, 4835 (1987)
C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 14, 99 (2002)
A. Maliakal, K. Raghavachari, H. Katz, E. Chandross, T. Siegrist, Chem. Mater. 16, 4980 (2004)
D. J. Gundlach, J. A. Nichols, L. Zhou, T. N. Jackson, Appl. Phys. Lett. 80, 2925 (2002)
C. D. Sheraw, T. N. Jackson, D. L. Eaton, J. E. Anthony, Adv. Mater. 15, 2209 (2003)
S. Traser, P. Wittmeyer, M. Rehahn, e-Polymers 32 (2002)
M. Ahles, R. Schmechel, H. von Seggern, Appl. Phys. Lett. 85, 4499 (2004)
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Roth, M., Rehahn, M., Ahles, M. et al. A General Synthetic Approach to Novel Bis(tetracenyl) Aromatics for OFET Application. MRS Online Proceedings Library 871, 629 (2005). https://doi.org/10.1557/PROC-871-I6.29