Gillen, DM, Hawes, CS ORCID: 0000-0001-6902-7939 and Gunnlaugsson, T (2018) 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, 83 (17). pp. 10398-10408. ISSN 0022-3263

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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.

Item Type: Article
Additional Information: The final published version of this article can be accessed online at https://pubs.acs.org/doi/10.1021/acs.joc.8b01481
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Chemical and Physical Sciences
Related URLs:
Depositing User: Symplectic
Date Deposited: 03 Sep 2018 08:19
Last Modified: 28 Sep 2018 13:45
URI: http://eprints.keele.ac.uk/id/eprint/5267

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