Hostname: page-component-7479d7b7d-767nl Total loading time: 0 Render date: 2024-07-12T02:42:20.460Z Has data issue: false hasContentIssue false
  • English
  • Français

A General Synthetic Approach to Novel Bis(tetracenyl) Aromatics for OFET Application

Published online by Cambridge University Press:  01 February 2011

Michael Roth ,
Matthias Rehahn ,
Marcus Ahles ,
Roland Schmechel  and
Heinz von Seggern
Michael Roth
Affiliation:
Ernst-Berl-Institute of Chemical Engineering and Macromolecular Science, Darmstadt University of Technology, Petersenstrasse 22, 64287 Darmstadt, Germany
Matthias Rehahn
Affiliation:
Ernst-Berl-Institute of Chemical Engineering and Macromolecular Science, Darmstadt University of Technology, Petersenstrasse 22, 64287 Darmstadt, Germany
Marcus Ahles
Affiliation:
Department of Materials Science, Electronic Materials Division, Darmstadt University of Technology, Petersenstrasse 23, 64287 Darmstadt, Germany
Roland Schmechel
Affiliation:
Department of Materials Science, Electronic Materials Division, Darmstadt University of Technology, Petersenstrasse 23, 64287 Darmstadt, Germany
Heinz von Seggern
Affiliation:
Department of Materials Science, Electronic Materials Division, Darmstadt University of Technology, Petersenstrasse 23, 64287 Darmstadt, Germany
Get access

Abstract

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[1], 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.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 871: Symposium I – Organic Thin-Film Electronics , 2005 , I6.29
Copyright
Copyright © Materials Research Society 2005

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

1 Luo, J., Hart, H., J. Org. Chem. 52, 4835 (1987)Google Scholar
2 Dimitrakopoulos, C. D., Malenfant, P. R. L., Adv. Mater. 14, 99 (2002)Google Scholar
3 Maliakal, A., Raghavachari, K., Katz, H., Chandross, E., Siegrist, T., Chem. Mater. 16, 4980 (2004)Google Scholar
4 Gundlach, D. J., Nichols, J. A., Zhou, L., Jackson, T. N., Appl. Phys. Lett. 80, 2925 (2002)Google Scholar
5 Sheraw, C. D., Jackson, T. N., Eaton, D. L., Anthony, J. E., Adv. Mater. 15, 2209 (2003)Google Scholar
6 Traser, S., Wittmeyer, P., Rehahn, M., e-Polymers 32 (2002)Google Scholar
7 Ahles, M., Schmechel, R., H. von Seggern, Appl. Phys. Lett. 85, 4499 (2004)Google Scholar