Citation:
Shu-Yun Zhu, Hong-Yu Guo, Fa-Fu Yang, Zu-Sheng Wang. Thiacalix[4]arene 1,2,3-triazole-polyethylene glycol polymers: Synthesis and dye adsorption properties[J]. Chinese Chemical Letters,
;2015, 26(9): 1091-1095.
doi:
10.1016/j.cclet.2015.03.031
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By reacting alkynylthiacalix[4]arenes with polyethylene glycol azido compounds, a series of novel thiacalix[4]arene 1,2,3-triazole-polyethylene glycol netty polymerswere conveniently prepared in good yields. Their structures and morphologies were studied by 1H NMR, IR, and elemental analysis and SEM images. On average, approximately 28-31 thiacalixarene units exist in each polymeric molecule. These novel polymers possess excellent adsorption ability for both cationic and anionic dyes. The saturation adsorption capacity for Congo red reached 1.3-1.4 mmol/g. They exhibit high and stable adsorption ability in the scope of pH 5-9, and maintain good properties in five cycles.
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Keywords:
- Thiacalix[4]arene,
- Synthesis,
- Polymer,
- Dye adsorption
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[1]
[1] Y.X. Wong, J. Yu, Laccase-catalyzed decolorization of synthetic dyes, Water Res. 33(1999) 3512-3520.
-
[2]
[2] G. Crini, Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment, Prog. Polym. Sci. 30(2005) 38-70.
-
[3]
[3] I.T. Peternel, N. Koprivanac, A.M.L. Božić, H.M. Kušić, Comparative study of UV/TiO2, UV/ZnO and photo-Fenton processes for the organic reactive dye degradation in aqueous solution, J. Hazard. Mater. 148(2007) 477-484.
-
[4]
[4] G. Crini, P.M. Badot, Application of chitosan, a natural aminopolysaccharide, for dye removal from aqueous solutions by adsorption processes using batch studies:a review of recent literature, Prog. Polym. Sci. 33(2008) 399-447.
-
[5]
[5] M.K. Purkait, S. DasGupta, S. De, Resistance in series model for micellar enhanced ultrafiltration of eosin dye, J. Colloid Interface Sci. 270(2004) 496-506.
-
[6]
[6] S. Chakraborty, M.K. Purkait, S. DasGupta, S. De, J.K. Basu, Nanofiltration of textile plant effluent for color removal and reduction in COD, Sep. Purif. Technol. 31(2003) 141-151.
-
[7]
[7] S.S. Li, X.Z. Kong, X.B. Jiang, X.L. Zhu, A novel and simple pathway to synthesis of porous polyurea absorbent and its tests on dye adsorption and desorption, Chin. Chem. Lett. 24(2013) 287-290.
-
[8]
[8] E. Akceylan, M. Bahadir, M. Yilmaz, Removal efficiency of a calix[4] arene-based polymer for water-soluble carcinogenic direct azo dyes and aromatic amines, J. Hazard. Mater. 162(2009) 960-966.
-
[9]
[9] A. Yilmaz, E. Yilmaz, M. Yilmaz, R.A. Bartsch, Removal of azo dyes from aqueous solutions using calix[4] arene and b-cyclodextrin, Dyes Pigment. 74(2007) 54-59.
-
[10]
[10] M.A. Kamboh, I.B. Solangi, S.T.H. Sherazi, S. Memon, Synthesis and application of p-tert-butylcalix[8] arene immobilized material for the removal of azo dyes, J. Hazard. Mater. 186(2011) 651-658.
-
[11]
[11] M. Chen, T. Shang, W. Fang, G.W. Diao, Study on adsorption and desorption properties of the starch grafted p-tert-butyl-calix[n]arene for butyl Rhodamine B solution, J. Hazard. Mater. 185(2011) 914-921.
-
[12]
[12] F.F. Yang, W.W. Liu, J.W. Xie, X.Y. Bai, H.Y. Guo, Novel deep-cavity calix[4] arene derivatives with large s-triazine conjugate systems:synthesis and complexation for dyes, J. Incl. Phenom. Macrocycl. Chem. 76(2013) 311-316.
-
[13]
[13] F.F. Yang, Y.M. Zhang, H.Y. Guo, X.L. Wei, High efficient liquid membrane transport of dyes using calix[4] arene-linked triphenylene dimers as carriers, Sep. Sci. Technol. 48(2013) 1565-1571.
-
[14]
[14] X.Y. Bai, F.F. Yang, J.W. Xie, H.Y. Guo, Novel 1,2-3,4-bridged and 1,3-bridged calix[4] arene based on large s-triazine conjugate systems:synthesis and complexation for dyes, J. Macromol. Sci. Part A Pure Appl. Chem. 50(2013) 334-339.
-
[15]
[15] N.M. Feng, H.Y. Zhao, J.Y. Zhan, D.M. Tian, H.B. Li, Switchable wettability sensor for ion pairs based on calix[4] azacrown clicking, Org. Lett. 14(2012) 1958-1961.
-
[16]
[16] J.Y. Zhan, F. Fang, D.M. Tian, H.B. Li, Anthraquinone-modified calix[4] arene:click synthesis, selective calcium ion fluorescent chemosensor and INHIBIT logic gate, Supramol. Chem. 24(2012) 272-278.
-
[17]
[17] B.Q. Hong, F.F. Yang, H.Y. Guo, Z.Y. Jiao, Synthesis, complexation and mesomorphism of novel calixarene-linked discotic triphenylene based on click chemistry, Tetrahedron Lett. 55(2014) 252-255.
-
[18]
[18] M.M. Song, Z.Y. Sun, C.P. Han, et al., Calixarene-based chemosensors by means of click chemistry, Chem. Asian J. 9(2014) 2344-2357.
-
[19]
[19] H.Y. Guo, F.F. Yang, Z.Y. Jiao, J.R. Lin, Click synthesis and dye extraction properties of novel thiacalix[4] arene derivatives with triazolyl and hydrogen bonding groups, Chin. Chem. Lett. 24(2013) 450-452.
-
[20]
[20] J.Y. Zhan, D.M. Tian, H.B. Li, Synthesis of calix[4] crowns containing soft and hard ion binding sites via click chemistry, New J. Chem. 33(2009) 725-728.
-
[21]
[21] F.F. Yang, X.Y. Bai, B.T. Xu, H.Y. Guo, Triphenylene-modified chitosan:novel high efficient sorbent for cationic and anionic dyes, Cellulose 20(2013) 895-906.
-
[22]
[22] K.L. Xie, W.G. Zhao, X.M. He, Adsorption properties of nano-cellulose hybrid containing polyhedral oligomeric silsesquioxane and removal of reactive dyes from aqueous solution, Carbohydr. Polym. 83(2011) 1516-1520.
-
[23]
[23] Y.H. Mao, Y. Guan, Q.K. Zheng, X.N. Feng, X.X. Wang, Adsorption thermodynamic and kinetic of disperse dye on cotton fiber modified with tolylene diisocyanate derivative, Cellulose 18(2011) 271-279.
-
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