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Thiacalix[4]arene derivatives containing multiple aromatic groups: High efficient extractants for organic dyes

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Abstract

Click reaction of alkynylthiacalix[4]arene with ethyl 2-azidoacetate, followed by ammonolysis with hydrazine hydrate and Schiff-base condensation with benzaldehyde or salicyic aldehyde, afforded two novel thiacalix[4]arene derivatives containing multiple aromatic groups in yields of 86% and 90%. Their complexation properties for four organic dyes were investigated by liquid-liquid extraction experiments, complexation UV-Vis spectra and mass spectrum. The highest extraction percentage was 97% for Neutral red. The UV-Vis spectra and ESI-MS spectrum indicated the 1:1 complexes in DMSO solution. The association constants were as high as 1 ∼ 8×104 M−1. These complexation experiments showed that thiacalix[4]arene receptors possess excellent complexation capabilities for dyes.

Two novel thiacalix[4]arene derivatives containing multiple aromatic groups were synthesized in yields of 86% and 90%. These complexation experiments showed that thiacalix[4]arene receptors possess excellent complexation capabilities for four tested dyes.

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Acknowledgements

Financial support from the National Natural Science Foundation of China (No: 21406036), Fujian Natural Science Foundation of China (No. 2014J01034), Project of Fujian provincial department of education(JA11044) and the Program for Innovative Research Team in Science and Technology in Fujian Province University and Program for Excellent young researchers in University of Fujian Province (JA10056) are greatly acknowledged.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Fujian Normal University, Fuzhou, 350007, P. R. China

    CHUANG YANG, ZUSHENG WANG, HONGYU GUO, ZIYU JIAO & FAFU YANG

  2. Fujian Key Laboratory of Polymer Materials, Fuzhou, 350007, P. R. China

    FAFU YANG

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  1. CHUANG YANG
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  2. ZUSHENG WANG
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  3. HONGYU GUO
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  4. ZIYU JIAO
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  5. FAFU YANG
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Corresponding author

Correspondence to FAFU YANG.

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Supplementary Information

The electronic supporting information, including the characteristic data of new compounds and the complexation UV-Vis spectra for dyes are available at www.ias.ac.in/chemsci.

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YANG, C., WANG, Z., GUO, H. et al. Thiacalix[4]arene derivatives containing multiple aromatic groups: High efficient extractants for organic dyes. J Chem Sci 127, 1383–1388 (2015). https://doi.org/10.1007/s12039-015-0911-1

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  • DOI: https://doi.org/10.1007/s12039-015-0911-1

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