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Calix[4]arene-Based 1,3-Diconjugate of Salicylyl Imine Having Dibenzyl Amine Moiety (L): Synthesis, Characterization, Receptor Properties toward Fe2+, Cu2+, and Zn2+, Crystal Structures of Its Zn2+ and Cu2+ Complexes, and Selective Phosphate Sensing by the [ZnL]

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    Calix[4]arene-Based 1,3-Diconjugate of Salicylyl Imine Having Dibenzyl Amine Moiety (L): Synthesis, Characterization, Receptor Properties toward Fe2+, Cu2+, and Zn2+, Crystal Structures of Its Zn2+ and Cu2+ Complexes, and Selective Phosphate Sensing by the [ZnL]
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    Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India
    E-mail: [email protected]. Phone: 91 22 2576 7162. Fax: 91 22 2572 3480.
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    Inorganic Chemistry

    Cite this: Inorg. Chem. 2011, 50, 15, 7050–7058
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    https://doi.org/10.1021/ic200544a
    Published July 1, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    A calix[4]arene conjugate bearing salicylyl imine having dibenzyl moiety (L) has been synthesized and characterized, and its ability to recognize three most important essential elements of human system, viz., iron, copper, and zinc, has been addressed by colorimetry and fluorescence techniques. L acts as a sensor for Cu2+ and Fe2+ by exhibiting visual color change and for Zn2+ based on fluorescence spectroscopy. L shows a minimum detection limit of 3.96 ± 0.42 and 4.51 ± 0.53 ppm and 45 ± 4 ppb, respectively, toward Fe2+, Cu2+, and Zn2+. The in situ prepared [ZnL] exhibits phosphate sensing among 14 anions studied with a detection limit of 247 ± 25 ppb. The complexes of Zn2+, Cu2+, and Fe2+ of L have been synthesized and characterized by different techniques. The crystalline nature of the zinc and copper complexes and the noncrystalline nature of simple L and its iron complex have been demonstrated by powder XRD. The structures of Cu2+ and Zn2+ complexes have been established by single crystal XRD wherein these were found to be 1:1 monomeric and 2:2 dimeric, respectively, using N2O2 as binding core. The geometries exhibited by the Zn2+ and the Cu2+ complexes were found to be distorted tetrahedral and distorted square planar, respectively. The iron complex of L exists in 1:1 stoichiometry as evident from the mass spectrometry and elemental analysis.

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    Supporting Information

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    Synthesis and characterization of precursor molecules, spectral data of L, 1H NMR spectra of 3, competitive color change experiments, minimum detection limit, spectral and XRD data of complexes, absorption spectral titration of [ZnL] with phosphates, and powder XRD studies. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Inorganic Chemistry

    Cite this: Inorg. Chem. 2011, 50, 15, 7050–7058
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ic200544a
    Published July 1, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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