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[C–H⋯anion] interactions mediate the templation and anion binding properties of topologically non-trivial metal–organic structures in aqueous solutions

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Chemical Science Vol - 7 Issue - 3

Chemical Science Vol - 7 Issue - 2

Chemical Science Vol -6

Chemical Science Vol -5

Chemical Science Vol -4

Chemical Science Vol -3

Chemical Science Vol -2

Chemical Science Vol -1

[C–H⋯anion] interactions mediate the templation and anion binding properties of topologically non-trivial metal–organic structures in aqueous solutions

Content Provider	Royal Society of Chemistry (RSC)
Author	Charbonnière, Loïc J. Trabolsi, Ali Khoury, Roberto El Prakasam, Thirumurugan Platas-Iglesias, Carlos Bilbeisi, Rana A. Olsen, John-Carl Elhabiri, Mourad Lusi, Matteo
Copyright Year	2016
Abstract	Two synthetic approaches—temperature variation and anion templation—allowed for the selective formation of a [2]catenane ([2]C4+) or a trefoil knot (TK6+), or for the enhanced formation of a Solomon link (SL8+), all from a simple set of starting materials (Zn(II) acetate, diformylpyridine (DFP) and a diamino-2,2′-bipyridine (DAB)) in mixed aqueous solutions. The catenane formed exclusively at 90 °C in a 1 : 1 mixed solvent of D2O and MeOD. In the presence of bromide ion as template, TK6+ formed exclusively at 50 °C in the same solvent. In the solid state, TK6+ hosts two bromide ions in its central cavity by forming six Csp2–H hydrogen bonds. In D2O, TK6+, which was originally prepared as a trifluoroacetate (TFA) salt, was found to exchange two TFA counterions for two monovalent anions of different sizes and shapes, which lodged within the knot's central cavity. In contrast to bromide, the larger triflate anion (CF3SO3−) promoted the formation of SL8+, which was characterized by 1H NMR spectroscopy and mass spectrometry. Two dimensional heteronuclear 19F-1H-HOSEY NMR experiments detected CH⋯F interactions inside the cavity of SL8+. Thus, the product distribution of this dynamic link forming system is sensitive to temperature and the size and shape of the anion template, and one of the products, TK6+, is capable of binding a variety of monovalent anions in D2O with high affinity (with log β2 values of 4 to 6 being typical).
Starting Page	2524
Ending Page	2531
Page Count	8
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	7
Issue Number	4
Journal	Chemical Science
DOI	10.1039/c5sc04246a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Trefoil knot Ion Nuclear magnetic resonance spectroscopy Digital audio broadcasting TFA Fluorine-19 nuclear magnetic resonance Bromide Trifluoromethanesulfonate Simple set Bipyridine Catenane Solvent Mass spectrometry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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

Ion-Solvent and Solvent-Solvent Interactions. X-ray Study of Aqueous Alkali Chloride Solutions

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Equilibria between iron-dinitrosy paramagnetic species in aqueous and alcoholic solutions studied by magnetic resonance spectroscopy

NUCLEAR MAGNETIC RESONANCE RELAXATION OF OXYGEN-17 IN AQUEOUS SOLUTIONS OF FERRIC ION

Nuclear Magnetic Resonance Relaxation of Oxygen-17 in Aqueous Solutions of Ferric Ion

Ultrasonic study of ion-solvent interactions in aqueous and non-aqueous solutions of transition and inner transition metal ions

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Almost positive links have negative signature, Abstracts of talks presented at the Topology (1991)

[C–H⋯anion] interactions mediate the templation and anion binding properties of topologically non-trivial metal–organic structures in aqueous solutions

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[C–H⋯anion] interactions mediate the templation and anion binding properties of topologically non-trivial metal–organic structures in aqueous solutions