New bis(azobenzocrown)s with dodecylmethylmalonyl linkers as ionophores for sodium selective potentiometric sensors

Autor: Mirosław Szarmach, Natalia Łukasik, Elżbieta Luboch, Maciej Jeszke
Rok vydání: 2016
Předmět:
Zdroj: Journal of Inclusion Phenomena and Macrocyclic Chemistry
ISSN: 1573-1111
1388-3127
DOI: 10.1007/s10847-016-0661-9
Popis: Novel biscrowns 1 and 2 were synthesized from 13-membered azobenzocrown ethers containing bromoalkylenoxy chains in para position relative to the azo group. The synthesized diester molecules are dodecylmethylmalonic acid derivatives differing by the linker length. The synthesized compounds have the potential of being used as sodium ionophores in ion-selective electrodes. They were characterized and used as ionophores in classic and miniature, solid contact (screen-printed and glassy carbon) membrane ion-selective electrodes. Compound 3, a similar monoester derivative of 13-membered azobenzocrown, was synthesized and used in membrane electrodes for comparison. Lipophilicity of new ionophores was determined by TLC. Lipophilicity of bis(azobenzocrown)s was found to be within the range of logPTLC = 12–13. It was observed that the particularly important selectivity coefficients logK Na,K determined for new electrodes, being logK Na,K = −2.5 and −2.6 (SSM, 0.1 M), are better than those of the electrodes featuring seven out of the nine commercially available sodium ionophores. It was concluded that the ionophore 1 creates, in acetone, with sodium iodide, complex of 1:1 stoichiometry (sandwich complex) with stability constant (logK) ca. 3.0.
Databáze: OpenAIRE