Thiazole-Containing Benzo-Crown Ethers:  A New Class of Ammonium-Selective Ionophores

A new class of crown ethers containing heterocyclic units has been designed to develop synthetic NH4 +-selective ionophores whose resulting potentiometric properties in solvent polymeric membranes are superior or at least comparable to those of nonactin. It was found that the derivatives of thiazole...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 2000-10, Vol.72 (19), p.4683-4688
Main Authors: Kim, Hong-Seok, Park, Hyun Joo, Oh, Hyun Joon, Koh, Young Kook, Choi, Jun-Hyeak, Lee, Dong-Hoon, Cha, Geun Sig, Nam, Hakhyun
Format: Article
Language:English
Subjects:
Analysis
Analytical chemistry
Chemistry
Electrochemistry
Electrodes: preparations and properties
Exact sciences and technology
General and physical chemistry
General, instrumentation
Ion selective electrodes
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Summary:A new class of crown ethers containing heterocyclic units has been designed to develop synthetic NH4 +-selective ionophores whose resulting potentiometric properties in solvent polymeric membranes are superior or at least comparable to those of nonactin. It was found that the derivatives of thiazole containing dibenzo-18-crown-6 (1; TDB18C6) incorporated in PVC-based membranes provide enhanced NH4 + selectivities over alkali metal cations, especially over Na+, compared to those of the nonactin-doped membranes:  for example, the selectivity coefficients, log (J = Li+, Na+, K+), for the 2-nitrophenyloctyl ether (NPOE) plasticized PVC membranes doped with the hexyl chain-substituted TDB18C6 (2) were −4.9, −3.9, and −1.3, while those for the same type of membranes with nonactin −4.4, −3.0, and −1.0, respectively. Unlike other synthetic NH4 +-selective neutral carriers reported to date, TDB18C6-type compounds result in potentiometric performance highly comparable to that of the nonactin-based ones except their slightly higher detection limits (∼3 × 10-6 vs 7 × 10-7). The complex formation between TDB18C6 and NH4 + was identified from 1H NMR spectra. The 1:1 complex formation constant of TDB18C6 with NH4 + in solvent polymeric membranes estimated using the method suggested by Bakker et al. and the NH4 + selectivity coefficient over K+ ( ) are ∼200 times smaller than that of nonactin (1.8 × 107 vs 3.6 × 109).
ISSN:0003-2700
1520-6882
DOI:10.1021/ac000177b