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

Research output: Contribution to journalArticlepeer-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 languageEnglish (US)
Pages (from-to)16474-16479
Number of pages6
JournalDalton Transactions
Volume46
Issue number47
DOIs
StatePublished - 2017

ASJC Scopus subject areas

  • Inorganic Chemistry

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