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Topological transformation of a trefoil knot into a [2]catenane

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Abstract

Topological transformation of a zinc-templated trefoil knot, Zn-TK, into a zinc-templated [2]catenane, Zn-[2]C, was studied. The net reaction 2 Zn-TK3 Zn-[2]C was accomplished in 89% yield by heating a solution of Zn-TK in D2O. Kinetic investigation by 1H NMR spectroscopy and high resolution mass spectrometry revealed that the mechanism is complex, involving a large pool of intermediates that form after imine bond cleavage. Bromide ions, which can occupy the central cavity of Zn-TK, inhibited the reaction. Two similar transformations were also studied, one of a cadmium-containing trefoil knot, Cd-TK, into a cadmium-containing catenane, Cd-[2]C, and the other of Cd-TK into Zn-[2]C. The latter transformation could be achieved in one step at high temperature or in two steps via transmetallation to form Zn-TK at room temperature followed by topological conversion of Zn-TK to Zn-[2]C at high temperature.

Graphical abstract: Topological transformation of a trefoil knot into a [2]catenane

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Publication details

The article was received on 22 Sep 2017, accepted on 23 Oct 2017 and first published on 23 Oct 2017


Article type: Paper
DOI: 10.1039/C7DT03582A
Citation: Dalton Trans., 2017, Advance Article
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    Topological transformation of a trefoil knot into a [2]catenane

    T. Prakasam, R. A. Bilbeisi, R. El-Khoury, L. J. Charbonnière, M. Elhabiri, G. Esposito, J. Olsen and A. Trabolsi, Dalton Trans., 2017, Advance Article , DOI: 10.1039/C7DT03582A

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