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

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.

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Correspondence to Michael Roth.

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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

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