Synthesis and Binding Properties of a Calix[4]crown-6-functionalized Polymeric Ion Acceptor

Wan-Ho Seol; Yu-Sun Yang; Chil-Won Lee; Myoung-Seon Gong

Macromolecular Research, Vol.12, No.4, 427-430, August, 2004

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Synthesis and Binding Properties of a Calix[4]crown-6-functionalized Polymeric Ion Acceptor

Wan-Ho Seol, Yu-Sun Yang, Chil-Won Lee, and Myoung-Seon Gong^†

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

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Calix[4]crown-6-2,4-bis(2-hydroxyethyl ether) (2), which has crown-6 moieties at the 1- and 3-positions and hydroxyethyl functions at the 2- and 4-positions, was prepared for the syntheses of polyester 3 and polyurethane 4 by reactions with adipoyl chloride and hexamethylene diisocyanate, respectively. The ion binding characteristics of monomer 2 and polymers 3 and 4 toward alkali and alkali earth metal ions were measured by liquid-liquid extraction from the aqueous phase into the organic phase. We observed that the polyurethane 4 has a higher binding affinity toward various metal cations when compared to polyester 3, which exhibits cesium ion selectivity.

Keywords:calix[4]crown-6;polyester;polyurethane;ion-binding

[References]

Vicens J, Bohmer V, Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer, Dordrecht (1991)
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)
Memon S, Yilmaz A, Yilmax M, J. Polym. Sci. A: Polym. Chem., 34, 4351 (1999)
Shinkai S, Kawaguchi H, Manabe O, J. Polym Sci. Part C: Polym. Lett., 26, 391 (1988)
Gravett DM, Guillet JE, Macromolecules, 29(2), 617 (1996)
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, 81 (1996)
Memon S, Ylmaz A, Yilmaz M, J. Macromol. Sci.-Pure Appl. Chem., 37, 865 (2000)
Seol WH, Kim SH, Lee CW, Gong MS, Bull. Korean Chem. Soc., in press
Deligoz H, Yilmaz M, Solvent Extr. Ion Exch., 13 (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)

[Referenced By]

[Related Articles]

[1] Vicens J, Bohmer V, Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer, Dordrecht (1991)

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

[3] 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)

[4] 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)

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

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

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

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

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

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

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

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

[13] Memon S, Yilmaz A, Yilmax M, J. Polym. Sci. A: Polym. Chem., 34, 4351 (1999)

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

[15] Gravett DM, Guillet JE, Macromolecules, 29(2), 617 (1996)

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

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

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

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

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

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

[22] Seol WH, Kim SH, Lee CW, Gong MS, Bull. Korean Chem. Soc., in press

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