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Anion binding properties of tris(2-hydroxyphenyl)methanes

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Abstract

Tris(2-hydroxyphenyl)methane derivatives (1) displayed excellent selectivity for Cl− in comparison with other anions tested (Br−, I− and NO3 −) by 1H NMR titration experiments. This selectivity is attributed to the fit size and shape of Cl−, which favor the formation of a stable host–guest complex with 1 through the multiple intermolecular hydrogen bonds.

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Fig. 1
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Notes

  1. The solubility of 1d to CDCl3 is fairly low.

  2. The IR spectra of 1 were measured in the presence or absence of 2 in CHCl3 ([1] = [2] = 3.0 mM) at 24 °C. With the addition of 2, the intensity of the initial OH stretching band of 1 at ca. 3,550 cm−1 decreased and that of a new band around 3,400 cm−1 increased. This spectral change is ascribed to the hydrogen bonding between the OH protons and the anion component of 2.

  3. In a nonpolar solvent, such as CDCl3, exchangeable protons that are neither hydrogen bonded nor locked in a hydrogen-bonded state exhibit small temperature dependences in their chemical shifts, while exchangeable protons that participate in an equilibrium between a hydrogen-bonded state and a non-hydrogen-bonded state exhibit large temperature dependencies.

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  1. Department of Chemistry and Chemical Engineering, Graduate School of Science and Engineering, Yamagata University, Jyonan 4-3-16, Yonezawa, 992-8510, Japan

    Tatsunori Sato & Kazuaki Ito

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  1. Tatsunori Sato
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  2. Kazuaki Ito
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Correspondence to Kazuaki Ito.

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Sato, T., Ito, K. Anion binding properties of tris(2-hydroxyphenyl)methanes. J Incl Phenom Macrocycl Chem 77, 385–394 (2013). https://doi.org/10.1007/s10847-012-0258-x

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