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Ion-Selective Electrodes Based on a Pyridyl-Containing Triazolophane: Altering Halide Selectivity by Combining Dipole-Promoted Cooperativity with Hydrogen Bonding

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    Ion-Selective Electrodes Based on a Pyridyl-Containing Triazolophane: Altering Halide Selectivity by Combining Dipole-Promoted Cooperativity with Hydrogen Bonding
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    † Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506, United States
    § Department of Chemistry, University of Miami, Coral Gables, Florida 33124, United States
    ‡ Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States
    *E-mail: [email protected]. Phone: +1(305) 284-4021. Fax: +1(305) 284-5637.
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    Analytical Chemistry

    Cite this: Anal. Chem. 2011, 83, 9, 3455–3461
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    https://doi.org/10.1021/ac200052q
    Published April 1, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    Triazolophanes are ionophores, with preorganized cyclic cavities that have tunable selectivities for halides. The interaction with halides is based on hydrogen bonding between the eight CH hydrogen atoms of the cavity and the halide anion. The rigidity of the cavity in tetraphenylene triazolophane along with the hydrogen bonding favors planar 1:1 complexation of “snugly” encapsulated chloride and bromide. Manipulating the triazolophane’s structure by introducing two pyridyl moieties into the cavity alters the receptor’s binding mode. This change adds a dipole-promoted driving force that combines with hydrogen bonding to favor the formation of 2:1 sandwich complexes around halides. The potentiometric response of electrodes based on this new ionophore was evaluated for optimal halide selectivity. The new triazolophane-based electrode showed an anti-Hofmeister selectivity toward iodide with a submicromolar detection limit. The stoichiometry of complexation and the stability constants with different halides were evaluated using a segmented sandwich membranes method. The pyridyl-triazolophane demonstrated a response consistent with a 2:1 sandwich-type complex with iodide, in polyvinyl chloride (PVC) membranes.

    Copyright © 2011 American Chemical Society

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    This article is cited by 42 publications.

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    Cite this: Anal. Chem. 2011, 83, 9, 3455–3461
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ac200052q
    Published April 1, 2011
    Copyright © 2011 American Chemical Society
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