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Li-selective calix[4]arene with trialkyl-monoacetic acid groups: effect of three alkyl branches and t-octyl groups at p-position on selectivity for Li extraction

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Abstract

Trialkyl-monoacetic acid derivatives of p–t-octylcalix[4]arene and calix[4]arene were prepared to investigate the effect of the alkyl branches attached to the phenoxy oxygen atoms and the p-position on the selective extraction of Li+ over Na+. Alkyl branches on the phenoxy oxygen atoms remarkably affected the Li+ selectivity, whereas those at the p-position had less effect. The former can contribute to excluding Na+ extraction while enabling Li+ extraction. Optimal selection of the alkyl branch improves the Li+ selectivity of calix[4]arene. However, sterically-hindered p–t-octylcalix[4]arene with three 2-ethylbutyl branches exhibited opposite selectivity.

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Acknowledgements

This work was financially supported in part by the Sasakawa Scientific Research Grant No. 25-301 from “The Japan Science Society” and by JSPS KAKENHI Grant Number (Grant-in-Aid for “Scientific Research (C) 25410192) from JSPS”. The NMR measurements were conducted at Analytical Research Center for Experimental Sciences, Saga University supported by “Project for Promoting Public Utilization of Advanced Research Infrastructure”. We would like to thank Editage (www.editage.com) for English language editing.

Funding

This study was funded by Japan Society for the Promotion of Science, KAKENHI (C) 25410192, Sasakawa Scientific Research Grant, 25-301.

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Authors and Affiliations

  1. Department of Chemistry and Applied Chemistry, Saga University, 1-Honjo, Saga, 840-8502, Japan

    Keisuke Ohto, Hirotoshi Sadamatsu, Takuya Hanada, Shintaro Morisada & Hidetaka Kawakita

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  1. Keisuke Ohto
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  2. Hirotoshi Sadamatsu
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  3. Takuya Hanada
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  4. Shintaro Morisada
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  5. Hidetaka Kawakita
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Contributions

KO planned this research work, elucidated the extraction mechanism, and wrote the paper. HS prepared most of the reagents, measured spectra data, and carried out extraction. TH prepared one of the reagents, measured spectra data, and carried out extraction. SM discussed with spectra data of the reagents. HK supported for the extraction reaction and for drawing the theoretical lines to estimate the extraction constants and separation factors.

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Correspondence to Keisuke Ohto.

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Ohto, K., Sadamatsu, H., Hanada, T. et al. Li-selective calix[4]arene with trialkyl-monoacetic acid groups: effect of three alkyl branches and t-octyl groups at p-position on selectivity for Li extraction. J Incl Phenom Macrocycl Chem (2024). https://doi.org/10.1007/s10847-024-01233-5

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