First Synthesis and Properties of Calix[4]arene with Two Alternately Arranged Phloroglucinols and Two p-tert-Butylphenols |
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| Authors: | Shingo Sato Hiroaki Iijima Norihiro Haga Kohbun Osono Hitoshi Mizuguchi Tatsuro Kijima |
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| Affiliation: | 1. Faculty of Engineering, Yamagata University, Department of Chemistry and Chemical Engineering , 4-3-16 Jonan, Yonezawa-shi, Yamagata, 992-8510, Japan shingo-s@yz.yamagata-u.ac.jp;3. Faculty of Engineering, Yamagata University, Department of Chemistry and Chemical Engineering , 4-3-16 Jonan, Yonezawa-shi, Yamagata, 992-8510, Japan |
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| Abstract: | ![]()
The Calix[4]arene 1 including two alternately arranged phloroglucinols and p-tert-butylphenols was synthesized via the “3+1” coupling procedure, and its pKa values were estimated to be 3–4 and 7.5, while those of the other six phenolic hydroxyls were approximately 11. Its UV–vis spectrum at pH 11 and 1H and 13C NMR spectra in NaOD-D2O solution (pH 12.8) showed a dramatic change like those of the phloroglucinol when compared to those in acidic or neutral solution, which suggests a change in the phloroglucinol moiety to the keto-form. During the solvent extraction for alkali metal species using 1, Li+ was only extracted in the low yield of 15% at pH 11. The cyclic voltammetry study of 1 was used to compare it with the phloroglucinol and p-tert-butylphenol. The redox potential of the corresponding two phloroglucinols was observed in 1. |
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| Keywords: | Calix[4]arene Phloroglucinol Keto-tautomer pKa Solvent extraction Redox potential |
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