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Issue 12, 2014
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Catenanes from catenanes: quantitative assessment of cooperativity in dynamic combinatorial catenation

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Abstract

A new azobenzene-based dithiol building block was developed which, upon oxidation, forms predominantly a [2]catenane consisting of two interlocked trimers. In the presence of cyclodextrin templates a series of [2] and [3]catenanes was formed instead. We developed a method that enabled estimating the equilibrium constants for catenation in all of these systems. The formation of the [3]catenanes is either cooperative or anticooperative, depending on the nature of the cyclodextrin. Using molecular dynamics simulations, we linked positive and negative cooperativity to, respectively, burying and exposure of hydrophobic surfaces upon catenation. Our results underline the importance of directly quantifying noncovalent interactions within catenanes, as the corresponding pseudo-rotaxane model systems were found to be poor predictors of binding interactions in the actual catenane.

Graphical abstract: Catenanes from catenanes: quantitative assessment of cooperativity in dynamic combinatorial catenation

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Publication details

The article was received on 04 Jul 2014, accepted on 17 Aug 2014 and first published on 20 Aug 2014


Article type: Edge Article
DOI: 10.1039/C4SC01998A
Citation: Chem. Sci., 2014,5, 4968-4974
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    Catenanes from catenanes: quantitative assessment of cooperativity in dynamic combinatorial catenation

    J. Li, P. Nowak, H. Fanlo-Virgós and S. Otto, Chem. Sci., 2014, 5, 4968
    DOI: 10.1039/C4SC01998A

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