TY - JOUR
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
N1 - Funding Information:
The research described here was sponsored by New York University Abu Dhabi, in the UAE. T. P., G. E and A. T. thank NYUAD for its generous support for the research program at NYUAD. We would like to acknowledge the Al Jalila Foundation (AJF201646) for funding this research work. The authors also thank the Core Technology Platforms at NYUAD. M. E. and L. C. thank the CNRS and the University of Strasbourg.
Publisher Copyright:
© 2017 The Royal Society of Chemistry.
Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
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.
UR - http://www.scopus.com/inward/record.url?scp=85037646156&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85037646156&partnerID=8YFLogxK
U2 - 10.1039/c7dt03582a
DO - 10.1039/c7dt03582a
M3 - Article
C2 - 29147692
AN - SCOPUS:85037646156
VL - 46
SP - 16474
EP - 16479
JO - Dalton Transactions
JF - Dalton Transactions
SN - 1477-9226
IS - 47
ER -