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Synthesis 2011(17): 2775-2780  
DOI: 10.1055/s-0030-1260123
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Preparation of Linear Aromatic Disulfonic Acids: New Linker Molecules for Metal-Organic Frameworks

Thomas W. T. Muesmann, Mathias S. Wickleder, Jens Christoffers*
Institut für Reine und Angewandte Chemie, Carl von Ossietzky-Universität Oldenburg, 26111 Oldenburg, Germany
Fax: +49(441)7983873; e-Mail: jens.christoffers@uni-oldenburg.de;
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Publication History

Received 10 May 2011
Publication Date:
20 July 2011 (online)

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Abstract

Four linear aromatic disulfonic acids were prepared, which are structurally similar to dicarboxylic acids commonly used as linker molecules for metal-organic frameworks. 4,4′-Biphenyl­disulfonic acid was prepared in three steps from 4,4′-dibromobiphenyl (54% overall yield). Direct sulfonation of terphenyl gave the respective all-para-constituted disulfonic acid in 73% yield. Tolane-4,4′-disulfonic acid was obtained by a three-step sequence consisting of Sonogashira coupling, oxidative degradation of a thioester, and hydrolysis in 20% overall yield. By using a Glaser coupling, the bis(4-sulfophenyl)butadiyne was analogously prepared in 30% overall yield.

Key words

alkynes - arenes - sulfur - cross coupling - metal-organic frameworks

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