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

Thirumurugan Prakasam; Rana A. Bilbeisi; Roberto El-Khoury; Loïc J. Charbonnière; Mourad Elhabiri; Gennaro Esposito; John Carl Olsen; Ali Trabolsi

doi:10.1039/c7dt03582a

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

Thirumurugan Prakasam, Rana A. Bilbeisi, Roberto El-Khoury, Loïc J. Charbonnière, Mourad Elhabiri, Gennaro Esposito, John Carl Olsen, Ali Trabolsi

Chemistry

Research output: Contribution to journal › Article › peer-review

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-TK → 3 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.

Original language	English (US)
Pages (from-to)	16474-16479
Number of pages	6
Journal	Dalton Transactions
Volume	46
Issue number	47
DOIs	https://doi.org/10.1039/c7dt03582a
State	Published - 2017

ASJC Scopus subject areas

Inorganic Chemistry

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@article{39072e425413466784a4c4eae4a4daff,

title = "Topological transformation of a trefoil knot into a [2]catenane",

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-TK → 3 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.",

author = "Thirumurugan Prakasam and Bilbeisi, {Rana A.} and Roberto El-Khoury and Charbonni{\`e}re, {Lo{\"i}c J.} and Mourad Elhabiri and Gennaro Esposito and Olsen, {John Carl} and Ali Trabolsi",

year = "2017",

doi = "10.1039/c7dt03582a",

language = "English (US)",

volume = "46",

pages = "16474--16479",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

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T1 - Topological transformation of a trefoil knot into a [2]catenane

AU - Prakasam, Thirumurugan

AU - Bilbeisi, Rana A.

AU - El-Khoury, Roberto

AU - Charbonnière, Loïc J.

AU - Elhabiri, Mourad

AU - Esposito, Gennaro

AU - Olsen, John Carl

AU - Trabolsi, Ali

PY - 2017

Y1 - 2017

N2 - 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-TK → 3 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.

AB - 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-TK → 3 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.

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