Synthesis and Properties of Calix[4]crown-6 Functionalized Polymers

Su-Han Kim; Chil-Won Lee; Young-Min Jeon; Myoung-Seon Gong

Macromolecular Research, Vol.13, No.2, 141-146, April, 2005

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Synthesis and Properties of Calix[4]crown-6 Functionalized Polymers

Su-Han Kim, Chil-Won Lee, Young-Min Jeon, and Myoung-Seon Gong^†

Department of Chemistry, Dankook University, Chungnam 330-714, Korea

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Calix[4]crown-6-2,4-bis(4-aminobutyl ether), which has a crown-6 moiety at the 1,3-position and amino function at the 2,4-position, was prepared as an intermediate for the subsequent synthesis of calix[4]crown-6-containing polyamide and polyimide using adipoyl chloride and 1,2,4,5-benzenetetracarboxylic dianhydride. The chemical structures were characterized by IR, 1H NMR spectroscopy and elemental analysis, and some of their physical properties, including their thermal behavior, were examined. The ion binding characteristics of the monomer and polymers for alkali metal and alkali earth metal ions were measured by liquid-liquid extraction from the aqueous phase into the organic phase. It has been observed that polyamide has a high binding ability towards various metal cations as compared to polyimide, which showed cesium ion selectivity.

Keywords:calix[4]crown-6;polyamide;polyimide;ion-binding

[References]

Castini A, Ungaro R, Asfari Z, Vicens J, in Calixarenes 2001, Z, Asfari, V. Bohmer, J. Harrowfield, and J. Vicens, Eds., Kluwer Academic, Dordrecht (2001)
Nicod L, Pellet-Rostaing S, Chitry F, Lemaire M, Tetrahedron, 39, 9443 (1998)
Kim JS, Lee WK, Sim WB, Ko JW, Cho MH, Ra DY, Kim JW, J. Incl. Phenom. Macrocycl. Chem., 37, 359 (2000)
Kim JS, Shon OJ, Sim WB, Kim SK, Cho MH, Kim JG, Suh IH, Kim DW, J. Chem. Soc.-Perkin Trans. 1, 1, 31 (2001)
Kim JS, Thuery P, Nierlich M, Rim JA, Yang SH, Lee JK, Cho KH, Lee JH, Vicens J, Bull. Korean Chem. Soc., 22, 321 (2001)
Reynier N, Dozol JF, Saadioui M, Asfari Z, Vicens J, Tetrahedron Lett., 39, 6461 (1998)
Neu FA, Weill MJS, Synth. Met., 90, 157 (1997)
Mathieu M, Asfari Z, Vicens J, Tetrahedron Lett., 43, 1225 (2002)
Asfari Z, Thuery P, Nierlich M, Vicens J, J. Tetrahedron Lett., 40, 499 (1999)
Bohmer V, Dorrenbacher R, Frings M, Heydenreich M, Paoli D, Vogt W, Ferguson G, Thondorf I, Tetrahedron Lett., 61, 549 (1996)
Jimenes CP, Escriche L, Casabo J, Anal. Chim. Acta, 371, 155 (1998)
Deligoz H, Tavasli M, Yilmaz M, J. Polym. Sci. A: Polym. Chem., 32(15), 2961 (1994)
Deligoz H, Yilmaz M, J. Polym. Sci. A: Polym. Chem., 33(16), 2851 (1995)
Yilmaz A, Memon S, Yilmaz M, J. Polym. Sci. A: Polym. Chem., 37(23), 4351 (1999)
Shinkai S, Kawaguchi H, Manabe O, J. Polym. Sci. Part C: Polym. Lett., 26, 391 (1988)
Gravett D, MGuillet JE, Macromolecules, 29, 617 (1997)
Ohto K, Tanaka Y, Inoue K, Chem. Lett., 647 (1997)
Kim JS, Kim SK, Ko JW, Talanta, 52, 1143 (2000)
Memon S, Uysal G, Yilmaz M, React. Funct. Polym., 47, 165 (2001)
Memon S, Uysal G, Yilmaz M, React. Funct. Polym., 50, 77 (2001)
Deligoz H, Yilmaz M, React. Funct. Polym., 31(2), 81 (1996)
Memon S, Ylmaz A, Yilmaz M, J. Macromol. Sci.-Pure Appl. Chem., 37, 865 (2000)
Deligoz H, Yilmaz M, Solvent Extr. Ion Exch., 13, 19 (1995)
Kim JS, Cho MH, Lee SC, Pang JH, Lee JH, Ohki A, Talanta, 49, 69 (1999)
Kim JS, Cho MH, Cho JH, Bartsch RA, Lee YI, Kim IH, Talanta, 51, 99 (2000)
Seol WH, Kim SH, Lee CW, Gong MS, Bull. Korean Chem. Soc., 25, 1265 (2004)
Seol WH, Yang YS, Lee CW, Gong MS, Macromol. Res., 12(4), 427 (2004)

[Referenced By]

[Related Articles]

[1] Castini A, Ungaro R, Asfari Z, Vicens J, in Calixarenes 2001, Z, Asfari, V. Bohmer, J. Harrowfield, and J. Vicens, Eds., Kluwer Academic, Dordrecht (2001)

[2] Nicod L, Pellet-Rostaing S, Chitry F, Lemaire M, Tetrahedron, 39, 9443 (1998)

[3] Kim JS, Lee WK, Sim WB, Ko JW, Cho MH, Ra DY, Kim JW, J. Incl. Phenom. Macrocycl. Chem., 37, 359 (2000)

[4] Kim JS, Shon OJ, Sim WB, Kim SK, Cho MH, Kim JG, Suh IH, Kim DW, J. Chem. Soc.-Perkin Trans. 1, 1, 31 (2001)

[5] Kim JS, Thuery P, Nierlich M, Rim JA, Yang SH, Lee JK, Cho KH, Lee JH, Vicens J, Bull. Korean Chem. Soc., 22, 321 (2001)

[6] Reynier N, Dozol JF, Saadioui M, Asfari Z, Vicens J, Tetrahedron Lett., 39, 6461 (1998)

[7] Neu FA, Weill MJS, Synth. Met., 90, 157 (1997)

[8] Mathieu M, Asfari Z, Vicens J, Tetrahedron Lett., 43, 1225 (2002)

[9] Asfari Z, Thuery P, Nierlich M, Vicens J, J. Tetrahedron Lett., 40, 499 (1999)

[10] Bohmer V, Dorrenbacher R, Frings M, Heydenreich M, Paoli D, Vogt W, Ferguson G, Thondorf I, Tetrahedron Lett., 61, 549 (1996)

[11] Jimenes CP, Escriche L, Casabo J, Anal. Chim. Acta, 371, 155 (1998)

[12] Deligoz H, Tavasli M, Yilmaz M, J. Polym. Sci. A: Polym. Chem., 32(15), 2961 (1994)

[13] Deligoz H, Yilmaz M, J. Polym. Sci. A: Polym. Chem., 33(16), 2851 (1995)

[14] Yilmaz A, Memon S, Yilmaz M, J. Polym. Sci. A: Polym. Chem., 37(23), 4351 (1999)

[15] Shinkai S, Kawaguchi H, Manabe O, J. Polym. Sci. Part C: Polym. Lett., 26, 391 (1988)

[16] Gravett D, MGuillet JE, Macromolecules, 29, 617 (1997)

[17] Ohto K, Tanaka Y, Inoue K, Chem. Lett., 647 (1997)

[18] Kim JS, Kim SK, Ko JW, Talanta, 52, 1143 (2000)

[19] Memon S, Uysal G, Yilmaz M, React. Funct. Polym., 47, 165 (2001)

[20] Memon S, Uysal G, Yilmaz M, React. Funct. Polym., 50, 77 (2001)

[21] Deligoz H, Yilmaz M, React. Funct. Polym., 31(2), 81 (1996)

[22] Memon S, Ylmaz A, Yilmaz M, J. Macromol. Sci.-Pure Appl. Chem., 37, 865 (2000)

[23] Deligoz H, Yilmaz M, Solvent Extr. Ion Exch., 13, 19 (1995)

[24] Kim JS, Cho MH, Lee SC, Pang JH, Lee JH, Ohki A, Talanta, 49, 69 (1999)

[25] Kim JS, Cho MH, Cho JH, Bartsch RA, Lee YI, Kim IH, Talanta, 51, 99 (2000)

[26] Seol WH, Kim SH, Lee CW, Gong MS, Bull. Korean Chem. Soc., 25, 1265 (2004)

[27] Seol WH, Yang YS, Lee CW, Gong MS, Macromol. Res., 12(4), 427 (2004)