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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
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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

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