Solution-State Anion Recognition, and Structural Studies, of a Series of Electron-Rich meta-Phenylene Bis(phenylurea) Receptors and Their Self-Assembled Structures
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2018Author:
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Gillen, D.M., Hawes, C.S., Gunnlaugsson, T., Solution-State Anion Recognition, and Structural Studies, of a Series of Electron-Rich meta-Phenylene Bis(phenylurea) Receptors and Their Self-Assembled Structures, Journal of Organic Chemistry, 2018 Sep 7;83(17):10398-10408Download Item:
Abstract:
meta-Phenylene bis(phenylurea) receptors 1-4 were designed and synthesized to investigate the association between receptor shape, anion-selective binding and anion-directed self-assembly processes. Solution studies, performed through 1H NMR titrations with a variety of tetra- N-butylammonium salts, demonstrated strong binding of 2 equiv of H2PO4-, AcO-, BzO- anions and comparatively weak binding of Cl-, HSO4-, and SO42- anions. Binding modes and stability constants (log β) were determined by regression analysis of the obtained 1H NMR titration data in DMSO- d6, and the cooperativities of the binding interactions were probed. Host-guest complexes of receptors 1 and 2 were studied in the crystalline phase to further probe the anion-binding behavior of this motif. This included a triple-stranded helicate consisting of three strands of receptor 2 arranged around a mixed-phosphate anionic core, which was characterized by using X-ray crystallography.
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Science Foundation Ireland
13/IA/1865
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http://people.tcd.ie/gunnlaut
Author: Gunnlaugsson, Thorfinnur
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Journal of Organic Chemistry;83;
17;
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Anion binding, Supramolecular chemistry, Ureas, Anion titration, Helicates, Anion templationDOI:
http://dx.doi.org/10.1021/acs.joc.8b01481Metadata
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