Synfacts 2013; 9(1): 0036
DOI: 10.1055/s-0032-1317887
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Redox-Switchable Cavitands: Molecular Grippers

Contributor(s):
Timothy M. Swager
,
Markrete Krikorian
Pochorovski I, Ebert M.-O, Gisselbrecht J.-P, Boudon C, Schweizer WB, Diederich F * ETH Zürich, Switzerland and Université de Strasbourg, France
Redox-Switchable Resorcin[4]arene Cavitands: Molecular Grippers.

J. Am. Chem. Soc. 2012;
134: 14702-14705
Further Information

Publication History

Publication Date:
17 December 2012 (online)

 

Significance

Here, a diquinone-based resorcin[4]arene cavitand goes from a kite to a vase form when reduced. The vase forms via hydrogen bonding between the central diols and the oxygens of the amides. This vase is stable even at –80 °C and can be used to capture the small molecule guests shown above. The molecules are shown in order of increasing association constant K a . The vase cavitand releases the guests upon oxidation.


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Comment

Both the kite and vase form are stable in deuterated chloroform, tetrahydrofuran, and mesitylene. After two to four days, the reduced form reverts into the oxidized form. A crystal structure of the reduced form has a 7.3° cavity, which allows it to encapsulate the solvent molecule mesitylene, as well as the larger guest molecules.


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