Synthesis of a Tweezer-like Bis(phenylthiapropoxy)calix[4]-arene as a Cation/π Enhanced Sensor for Ion-Selective Electrodes
Hao Sun
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Department of Chemistry, Tianjin University, Tianjin 300072, China
Search for more papers by this authorXian-Shun Zeng
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorJian-Quan Liu
Department of Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorXue-Bing Leng
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorChen Qi-Fa
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorFeng-Bo Xu
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorQing-Shan Li
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorXi-Wen He
Department of Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorWen-Qin Zhang
Department of Chemistry, Tianjin University, Tianjin 300072, China
Search for more papers by this authorZheng-Zhi Zhang
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorHao Sun
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Department of Chemistry, Tianjin University, Tianjin 300072, China
Search for more papers by this authorXian-Shun Zeng
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorJian-Quan Liu
Department of Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorXue-Bing Leng
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorChen Qi-Fa
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorFeng-Bo Xu
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorQing-Shan Li
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorXi-Wen He
Department of Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorWen-Qin Zhang
Department of Chemistry, Tianjin University, Tianjin 300072, China
Search for more papers by this authorZheng-Zhi Zhang
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorAbstract
Two novel 25,27-dihydroxy-26,28-bis(3-phenyilhiapropoxy)-calix[4]arene (3) and 25,27-dihydroxy-26,28-bis(3-phenylthiapropoxy)-5,11, 17, 23-tetra-tert-butylcalix[4]arene (4) were synthesized for the evaluation of their ion-selectivity in ion-selective electrodes (ISEs). ISEs based on 3 and 4 as neutral ionophores were prepared, and their selectivity coefficients for Ag+ (lg Apotag,M) were investigated against other alkali metal, alkaline-earth metal, aluminum, thallium (I), lead and some transition metal ions using the separate solution method (SSM). These ISEs showed excellent Ag+ selectivity over most of the interfering cations examined, except for Hg2+ and Fe2+ having relative smaller interference (Ig Kpotag,M≤ − 2.1).
References
- 1(a) Gutsche, C. D. Calixarenes, The Royal Society of Chemistry, Cambridge, UK, 1998. (b) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713. (c) Böhmer, V. Angew. Chan., Int. Ed. Engl. 1995, 43, 713. (d) Bühlmann, P.; Pretsch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593. (e) Bakker, E.; Bühlmann, P.; Pretsch, E. Chemn. Rev. 1997, 97, 3083.
- 2(a) Cunningham, K.; Svehla, G.; McKervey, M. A.; Harris, S. J. Anal. Proc. 1991, 28, 294. (b) Telting-Diaz, M.; Regan, F.; Diamond, D.; Smyth, M. R. J. Pharm. Biomed. Anal. 1990, 8, 695. (c) Cadogan, A.; Gao, Z.; Lewenstam, A.; Ivaska, A.; Diamond, D. Anal. Chem. 1992, 64, 2496.
- 3(a) Yamamoto, H.; Shinkai, S. Chem. Lett. 1994, 1115. (b) Yamamoto, H.; Ueda, K.; Suenaga, H.; Sakaki, T.; Shinkai, S. Chem. Lett. 1996, 39.
- 4 Careri, M.; Casnati, A.; Guaarinoni, A.; Mangia, A.; Mori, G.; Pochini, A.; Ungaro, R. Anal. Chem. 1993, 65, 3156.
- 5(a) Brunink, J. A. J.; Haak, J. R.; Bomer, J. B.; Reinhoudt, D. N.; McKervey, M. A.; Harris, S. J. Anal. Chim. Acta 1991, 254, 75. (b) Reinhoudt, D. N. Sens. Actuators, B 1995, 24–25, 197.
- 6 Kimura, K.; Matsuba, T.; Tsujimura, Y.; Yokoyama, M. Anal. Chem. 1992, 64, 2508.
- 7 Tsujimura, Y.; Yokoyama, M.; Kimura, K. Anal. Chem. 1995, 67, 2401.
- 8(a) Zeng, X.; Weng, L.; Chen, L.; Ju, H.; Leng, X.; He, X.; Zhang, Z. Z. Chin. J. Chem. 2001, 19 (5), 493. (b) Chen, L.; Ju, H.; Zeng, X.; He, X.; Zhang, Z. Z. Anal. Chim. Acta 2001, 447, 41.
- 9 Bocchi, C.; Careri, M.; Casnati, A.; Mori, G. Anal. Chem. 1995, 67, 4234.
- 10 Cobben, P. L. H. M.; Egberink, R. J. M.; Bomer, J. G.; Bergveld, P.; Verboom, W.; Reinhoudt, D. N. J. Am. Chem. Soc. 1992, 114, 10573.
- 11 Malinowska, E.; Brzozka, Z.; Kasiura, K.; Egberink, R. J.; Reinhoudt, D. N. Anal. Chim. Acta 1994, 298, 245.
- 12 Zeng, X.; Weng, L.; Chen, L.; Leng, X.; Zhang, Z. Z.; He, X. Tetrahedron Lett. 2000, 41, 4917.
- 13 Zeng, X.; Weng, L.; Chen, L.; Leng, X.; Ju, H.; He, X.; Zhang, Z. Z. J. Chem. Soc., Perkin Trans. 2 2001, 545.
- 14 Zeng, X.; Han, X.; Chen, L.; Li, Q.; Xu, F.; He, X.; Zhang, Z. Z. Tetrahedron Lett. 2002, 43, 131.
- 15 Zeng, X.; Weng, L.; Chen, L.; Xu, F.; Li, Q.; Leng, X.; He, X.; Zhang, Z. Z. Tetrahedron 2002, 58, 2647.
- 16 Zeng, X.; Leng, X.; Chen, L.; Sun, H.; Xu, F.; Li, Q.; He, X.; Zhang, Z. Z. J. Chem. Soc., Perkin Tram. 2 2002, 796.
- 17 Chen, L.; Ju, H.; Zeng, X.; He, X.; Zhang, Z. Z. Anal. Chim. Acta 2001, 437, 191.
- 18 Chen, L.; Zeng, X.; Ju, H.; He, X.; Zhang, Z. Z. Microchem. J. 2000, 65, 129.
- 19 Chen, L.; Zeng, X.; He, X.; Zhang, Z. Z. Fresenius' J. Anal. Chan. 2000, 367, 535.
- 20
Zeng, X.;
Chen, L.;
Weng, L.;
Leng, X.;
Ju, H.;
He, X.;
Zhang, Z. Z.
J. Chem. Res. Synop.
2000,
518.
10.3184/030823400103165978 Google Scholar
- 21 Li, Z. T.; Ji, G. Z.; Zhao, C. K.; Yuan, S. D.; Ding, H.; Huang, C.; Du, A. L.; Wei, M. J. Org. Chan. 1999, 64, 3572.
- 22 Kimuia, K.; Shona, T. In Cation Binding by Macrocycles, Eds.: Y. Inoue; G. W. Gokel Marcel Dekker, New York, 1990, p. 429.
- 23(a) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303. (b) See also our work about Ag+ -π interaction in the solid state: Xu, F.; Weng, L.; Sun, L.; Zhang, Z. Z.; Zhou, Z. Organometallics 2000, 19, 2658.
- 24 Werner, E. M. Anal. Chan. 1977, 49, 810.