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Urea-Functionalized M4L6 Cage Receptors: Self-Assembly, Dynamics, and Anion Recognition in Aqueous Solutions

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/ja300677w· OSTI ID:1042887
We present an extensive study of a novel class of de novo designed tetrahedral M{sub 4}L{sub 6} (M = Ni, Zn) cage receptors, wherein internal decoration of the cage cavities with urea anion-binding groups, via functionalization of the organic components L, led to selective encapsulation of tetrahedral oxoanions EO{sub 4}{sup -} (E = S, Se, Cr, Mo, W, n = 2; E = P, n = 3) from aqueous solutions, based on shape, size, and charge recognition. External functionalization with tBu groups led to enhanced solubility of the cages in aqueous methanol solutions, thereby allowing for their thorough characterization by multinuclear ({sup 1}H, {sup 13}C, {sup 77}Se) and diffusion NMR spectroscopies. Additional experimental characterization by electrospray ionization mass spectrometry, UV-vis spectroscopy, and single-crystal X-ray diffraction, as well as theoretical calculations, led to a detailed understanding of the cage structures, self-assembly, and anion encapsulation. We found that the cage self-assembly is templated by EO{sub 4}{sup -} oxoanions (n {ge} 2), and upon removal of the templating anion the tetrahedral M{sub 4}L{sub 6} cages rearrange into different coordination assemblies. The exchange selectivity among EO{sub 4}{sup -} oxoanions has been investigated with {sup 77}Se NMR spectroscopy using {sup 77}SeO{sub 4}{sup 2-} as an anionic probe, which found the following selectivity trend: PO{sub 4}{sup 3-} CrO{sub 4}{sup 2-} > SO{sub 4}{sup 2-} > SeO{sub 4}{sup 2-} > MoO{sub 4}{sup 2-} > WO{sub 4}{sup 2-}. In addition to the complementarity and flexibility of the cage receptor, a combination of factors have been found to contribute to the observed anion selectivity, including the anions charge, size, hydration, basicity, and hydrogen-bond acceptor abilities.
Research Organization:
Oak Ridge National Laboratory (ORNL); Center for Nanophase Materials Sciences
Sponsoring Organization:
SC USDOE - Office of Science (SC)
DOE Contract Number:
AC05-00OR22725
OSTI ID:
1042887
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 20 Vol. 134; ISSN JACSAT; ISSN 0002-7863
Country of Publication:
United States
Language:
English