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Issue 20, 2004
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Synthesis and ligand properties of thianthrenophane

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Thianthrenophane 1 has a cavity which offers enough room to potentially enable endohedral coordination to small ions or molecules. For the complexation of silver(I) perchlorate the complex stability constants of 1 log K1 = 5.45 ± 0.13 and of thianthrene log K2 = 9.16 ± 0.10 were determined by UV/Vis titration. Single competition transport experiments with ten metal salts demonstrate a very high selectivity of 1 as a carrier for silver(I) and a distinctly higher transport rate compared to carriers such as thianthrene and 1,4,8,11-tetrathiacyclotetradecane (14-ane-S4). Although the X-ray crystal structure analysis of the polymeric [Ag(1)]ClO4·(dioxane)7 complex shows an exohedral coordination to silver(I) we suggest that the formation of an endohedral [Ag(1)]+ complex is the explanation for the unusual carrier selectivity of silver(I) by 1 in bulk liquid membrane.

Graphical abstract: Synthesis and ligand properties of thianthrenophane

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Publication details

The article was received on 11 May 2004, accepted on 17 Aug 2004 and first published on 21 Sep 2004

Article type: Paper
DOI: 10.1039/B407048H
Org. Biomol. Chem., 2004,2, 2897-2901

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    Synthesis and ligand properties of thianthrenophane

    S. Amthor, C. Lambert, B. Graser, D. Leusser, C. Selinka and D. Stalke, Org. Biomol. Chem., 2004, 2, 2897
    DOI: 10.1039/B407048H

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