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CH···anion bonds that template zinc molecular knots

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Weak C–H···anion contacts in water/methanol steer a Zn(II) dynamic library toward a trefoil knot that binds two bromides in its cavity.

Source

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

Bilbeisi RA, Prakasam T, Lusi M, et al. · Chemical science · 2016

doi.org/10.1039/c5sc04246aRead the full paper ↗38 citationscc by

Study at a glance

Design
Other — Zn(II)-templated DFP/DAB assemblies (catenane/knot/link) with aqueous anion-binding studies
N
Supramolecular synthesis and binding — no sample N
Population
DFP–DAB–Zn(II) interlocked assemblies in MeOD/D2O
Outcome
CH···anion-mediated topology selection and aqueous anion binding

Structured fields used in claim comparison tables when every cited study has a complete layer.

What they did

Authors assembled DFP + DAB with Zn(II), used anion templation and temperature to bias [2]catenane, trefoil knot TK6+ and Solomon link, solved TK6+ crystals with two bromides, computed ESP/dipole, and studied aqueous anion binding by NMR.

What they found

CH···anion interactions in MeOD/D2O mediate topology. Solid-state TK6+ holds two bromides via bipyridinyl C–H hydrogen bonds. Cavity ~130 Å3 fits two anions ≤2.5 Å. DFT dipole is 2.77 D (gas) and 4.97 D (water). TK6+ still binds anions in D2O.

The limits

What it doesn't show

A full aqueous Kd table for every anion under physiological salt is incomplete; TFA association mode could not be assigned by HOESY.

Key terms

Trefoil knot (TK6+)
Zn(II)-templated three-crossing knot that binds anions in its central cavity.
CH···anion interaction
Weak hydrogen bond from an aromatic C–H (bipyridine) to Br− or similar.
[2]Catenane / Solomon link
Other members of the same imine/Zn dynamic library.
Anion templation
Anions that bias which topology forms from the dynamic library.
DFP / DAB ligands
Diformylpyridine and diamino-bipyridine building blocks.

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Templating interaction in MeOD/D2O:

Common questions

What weak interaction templates the knot?

CH···anion contacts in MeOD/D2O.

How many bromides in the crystal cavity?

Two.

Cavity volume?

About 130 Å3.

Does binding survive in D2O?

Yes for TK6+.

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