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Synthesis 2009(1): 79-84  
DOI: 10.1055/s-0028-1083260
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized Oligophenylenes and Oligoarylenes Bearing Heteroaryl Groups

Ivonne Wallmanna, Gregor Schnakenburgb, Arne Lützen*a
a Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)739608; e-Mail: arne.luetzen@uni-bonn.de;
b Institute of Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
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Publication History

Received 20 October 2008
Publication Date:
12 December 2008 (online)

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Abstract

Oligo-p-phenylenes have proven to be versatile building blocks for the generation of self-assembled nanoaggregates via vapour deposition on solid supports whose optical properties and morphologies can be influenced by the introduction of functional groups. These aggregates show strong polarized luminescence and they have been demonstrated to have wave-guiding, lasing and even non-linear optical properties (e.g., frequency doubling) when the molecular building blocks are suitably functionalized. Thus, there is a demand for the synthesis of further functionalised p-phenylenes because similar properties can be expected from derivatives incorporating heteroaryl groups in the oligoarylene scaffold such as thiophenes, pyridines or carbazole units. The synthesis of such derivatives using a reliable Suzuki cross-coupling strategy is presented here.

Key words

π-conjugated molecules - oligo-p-phenylenes - thiophenes - carbazoles - Suzuki cross-coupling