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Synthesis of novel calix[6]-1,4-crown-based netty polymer and its excellent adsorption capabilities for aniline derivatives

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Abstract

By introducing four ester groups on p-tert-butylcalix[6]-1,4-crown-4 and then ammonolysis with ethanolamine, p-tert-butylcalix[6]-1,4-crown-4 amido derivative with four terminal hydroxyl groups (4) was obtained in good yield. Further by reacting compound 4 with 1,1,1-tris(tosylatemethyl)propane (6) in NaH/THF system, the novel netty calix[6]-1,4-crown-based polymer 7 was prepared in “4+3” condensation mode. The structure of polymer 7 was confirmed by elemental analysis, IR and 1H NMR spectra. The loose pores and cross-linked netty architecture were observed for polymer 7 in its SEM images. The M n of polymer 7 was 39,816 which indicated an average of approximately 23 calixarene units in each polymer molecule. Polymer 7 exhibited outstanding adsorption abilities for series of aniline derivatives (aniline, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-nitroaniline, m-nitroaniline and p-nitroaniline). The adsorption percentages for these aniline derivatives were above 90 %. The saturation adsorption capacities for aniline and p-nitroaniline were as high as 2.30 and 2.22 mmol/g, respectively. The adsorption abilities of polymer 7 kept stable at pH 6–10 and it could be re-used after desorption of 10 % HCl. The high adsorption abilities of polymer 7 for aniline derivatives were not just because of π–π stack action of the phenyl groups and the hydrogen bond action, but also due to the stable conformation of calix[6]arene skeleton and big cavity, which were favorable for adsorption of aniline derivatives.

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Acknowledgments

Financial support from the National Natural Science Foundation of China (No: 20402002), Fujian Natural Science Foundation of China (No. 2011J01031), Project of Fujian Provincial Department of Education (JA11044) and Program for Excellent young researchers in University of Fujian Province (JA10056) were greatly acknowledged.

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Authors and Affiliations

  1. College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, 350007, People’s Republic of China

    Hongyu Guo, Fafu Yang, Xianfeng Chai, Ziyu Jiao & Congcong Li

  2. Fujian Key Laboratory of Polymer Materials, Fujian Normal University, Fuzhou, 350007, People’s Republic of China

    Fafu Yang

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  1. Hongyu Guo
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  2. Fafu Yang
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  3. Xianfeng Chai
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  4. Ziyu Jiao
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  5. Congcong Li
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Correspondence to Fafu Yang.

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Guo, H., Yang, F., Chai, X. et al. Synthesis of novel calix[6]-1,4-crown-based netty polymer and its excellent adsorption capabilities for aniline derivatives. Iran Polym J 21, 451–456 (2012). https://doi.org/10.1007/s13726-012-0048-8

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  • DOI: https://doi.org/10.1007/s13726-012-0048-8

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