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Synthesis and Properties of 1,3,5-Tris(phenoxymethyl)-2,4,6-triethylbenzenes as NH 4 + Ionophores

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Abstract

The synthesis, spectroscopic characterization, and potentiometricmeasurements of new 1,3,5-trisphenoxy-2,4,6-triethylbenzenesare described. The cation binding abilities oftrisphenoxy-2,4,6-triethylbenzenes were strongly dependenton the substituents introduced on the phenoxy units: thereceptors with electron-donating alkoxy groups (–OCH3and –OCH2C6H5) provided similar potentiometricperformance to that of nonactin in PVC-based, ion-selectivemembrane electrodes. The trisphenoxy-2,4,6-triethylbenzenereceptors with ether groups on ortho and meta positions ofphenoxy units exhibit almost identical cation recognitionproperties in the PVC membranes. It is postulated that theelectron-donating nature of the alkoxy substituents increases theelectron density in the phenoxy units, resulting in increasedcation-π interactions.

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Kim, HS., Kim, DH., Kim, K.S. et al. Synthesis and Properties of 1,3,5-Tris(phenoxymethyl)-2,4,6-triethylbenzenes as NH 4 + Ionophores. Journal of Inclusion Phenomena 46, 201–205 (2003). https://doi.org/10.1023/A:1026331014375

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  • DOI: https://doi.org/10.1023/A:1026331014375

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