Browse > Article
http://dx.doi.org/10.5012/bkcs.2008.29.2.417

Synthesis and Binding Properties of 1,3,5-Tris(2-arylthiomethyl)mesitylene: A Selective Ag (I) Ionophore  

Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
Bae, Seon-Yun (Department of Applied Chemistry, Kyungpook National University)
Kim, Ki-Soo (Department of Applied Chemistry, Kyungpook National University)
Choi, Jun-Hyeak (Department of Applied Chemistry, Kyungpook National University)
Choi, Heung-Jin (Department of Applied Chemistry, Kyungpook National University)
Shim, Jun-Ho (Chemical Sensor Research Group, Department of Chemistry, Kwangwoon University)
Cha, Geun-Sig (Chemical Sensor Research Group, Department of Chemistry, Kwangwoon University)
Nam, Hak-Hyun (Chemical Sensor Research Group, Department of Chemistry, Kwangwoon University)
Publication Information
Abstract
The efficient synthesis of four mesitylene-based receptors 1-4 and their potentiometric response characteristics to alkali metal, alkaline earth metal, and transition metal ions, under various pH conditions are outlined. Receptor 1-based electrode exhibited more sensitive response to Ag+ ion (49 mV/decade of range from 10-6 to 10-2 M) than the 2-based electrode (47 mV/decade of range from 3 ´ 10-5 to 10-2 M), while the 3- and 4-based ones revealed sub-Nernstian below 40 mV/pAg+. All electrodes showed substantial responses to Ag+ ion under acidic condition, but there was almost nil-response to other transition metal ions (Fe2+, Co2+, Zn2+, Ni2+, Pb2+, Cd2+, Cu2+ and Hg2+). The association constant of receptor 1 toward Ag+ ion, measured by 1H NMR titration, showed the largest value (200 M-1) among the tested receptors. The results were interpreted with semi empirically-modeled structures.
Keywords
Tripodal receptor; Mesitylene; NMR titration; ISE; Silver ion selective
Citations & Related Records
Times Cited By KSCI : 6  (Citation Analysis)
Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 3
연도 인용수 순위
1 Akhond, M.; Ghaedi, M.; Tashkhourian, J. Bull. Korean Chem. Soc. 2005, 26, 882   DOI   ScienceOn
2 Kim, H.-S.; Do, K. S.; Kim, K. S.; Shim, J. H.; Cha, G. S.; Nam, H. Bull. Korean Chem. Soc. 2004, 25, 1465   DOI   ScienceOn
3 Kwon, O.-S.; Kim, H.-S. Supramol. Chem. 2007, 19, 277   DOI   ScienceOn
4 Jeon, Y.-M.; Lim, T.-H.; Kim, J.-G.; Kim, J.-S.; Gong, M.-S. Bull Korean Chem. Soc. 2007, 28, 816   DOI   ScienceOn
5 van der Made, A. W.; van der Made, R. H. J. Org. Chem. 1993, 58, 1262   DOI
6 Vacca, A.; Nativi, C.; Cacciarini, M.; Pergoli, R.; Roelens, S. J. Am. Chem. Soc. 2004, 126, 16456   DOI   ScienceOn
7 Akhond, M.; Tashkhourian, J. Bull. Korean Chem. Soc. 2003, 24, 489   DOI   ScienceOn
8 Hiraoka, S.; Yi, T.; Shiro, M.; Shinoya, M. J. Am. Chem. Soc. 2002, 124, 14510   DOI   ScienceOn
9 Kim, B. H.; Hong, H. P.; Cho, K. T.; On, J. H.; Jun, Y. M.; Jeong, I. S.; Cha, G. S.; Nam, H. Talanta 2005, 66, 794   DOI   ScienceOn
10 Kim, J.; Raman, B.; Ahn, K. H. J. Org. Chem. 2006, 71, 38   DOI   ScienceOn
11 Higuchi, H.; Matsufuji, T.; Oshima, T.; Ohto, K.; Inoue, K.; Tsend-Ayush, T.; Gloe, K. Chem. Lett. 2005, 34, 80   DOI   ScienceOn
12 Wygladacz, K.; Radu, A.; Xu, C.; Qin, Y.; Bakker, E. Anal. Chem. 2005, 77, 4706   DOI   ScienceOn
13 Zhang, X.-B.; Han, Z.-X.; Fang, Z.-H.; Shen, G..-L.; Yu, R.-Q. Anal. Chim. Acta 2006, 562, 210   DOI   ScienceOn
14 Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; John Wiley & Sons Ltd.: 2000
15 Zeng, X.; Weng, L.; Chen, L.; Xu, F.; Li, Q.; Leng, X.; He, X.; Zhang, Z. Tetrahedron 2002, 58, 2647   DOI   ScienceOn
16 Lu, J.; He, X.; Zeng, X.; Wan, Q.; Zhang, Z. Talanta 2003, 59, 553   DOI   ScienceOn
17 Kim, Y. H.; Cha, N. R.; Chang, S-K. Tetrahedron Lett. 2002, 43, 3883   DOI   ScienceOn
18 Chen, L.; Ju, H.; Zeng, X.; He, X.; Zhang, Z. Anal. Chim Acta 2001, 437, 191   DOI   ScienceOn
19 Morakot, N.; Tomapatanaget, B.; Ngeon-Tae, W.; Aeungmaitrepirom, W.; Tuntylani, T. Supramol. Chem. 2005, 17, 655   DOI   ScienceOn
20 Sasaki, S.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc., Perkin Trans. 2 2001, 2309
21 Stack, T. D. P.; Hou, Z.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6466   DOI   ScienceOn
22 Kim, H.-S.; Kim, D.-H.; Kim, K. S.; Choi, J.-H.; Choi, H. J.; Kim, S. H.; Shim, J. H.; Cha, G. S.; Nam, H. Talanta 2007, 71, 1986   DOI   ScienceOn
23 Rutrack, K.; Koval'chuck, A.; Bricks, J. L.; Slominskii, J. L. J. Am. Chem. Soc. 2001, 123, 6205   DOI   ScienceOn
24 Matsumoto, K.; Hashimoto, M.; Toda, M.; Tsukube, H. J. Chem. Soc., Perkin Trans. 1 1995, 2497
25 Isildak, I.; Yolcu, M.; Isildak, O.; Topal, G.; Horsgoren, H. Microchim. Acta 2004, 144, 177   DOI   ScienceOn
26 Su, C. C.; Chang, M. C.; Liu, L. L. K. Anal. Chim. Acta 2001, 432, 261   DOI   ScienceOn
27 Xie, J.; Zheng, Q.-Y.; Zheng, Y.-S.; Chen, C.-F.; Huang, Z.-T. J. Incl. Phenom. 2001, 40, 125   DOI   ScienceOn
28 Chen, L.; Zeng, X.; Ju, H.; He, X.; Zhang, Z. J. Microchem. 2000, 65, 129   DOI   ScienceOn
29 Park, S. B.; Yoon, I.; Seo, J.; Kim, H. J.; Kim, J. S.; Lee, S. S. Bull. Korean Chem. Soc. 2006, 27, 713   DOI   ScienceOn
30 Goldcamp, M. J.; Ashley, K.; Edison, S. E.; Pretty, J.; Shumaker, J. Electroanalysis 2005, 17, 1015   DOI   ScienceOn
31 Zeng, X.; Weng, L.; Chen, L.; Leng, X.; Ju, H.; Zhang, Z. J. Chem. Soc. Perkin Trans. 2 2001, 545
32 Turner, D. R.; Paterson, M. J.; Steed, J. W. J. Org. Chem. 2005, 71, 1598   DOI   ScienceOn
33 Seong, H. R.; Kim, D.-S.; Kim, S. G.; Choi, H.-J.; Ahn, K. H. Tetrahedron Lett. 2004, 45, 723   DOI   ScienceOn
34 Shim, J. H.; Jeong, I. S.; Lee, M. H.; Hong, H. P.; On, J. H.; Kim, K. S.; Kim, H.-S.; Kim, B. H.; Cha, G. S.; Nam, H. Talanta 2004, 63, 61   DOI   ScienceOn
35 Hennrich, G.; Anslyn, E. V. Chem. Eur. J. 2002, 8, 2219, references cited therein
36 Kariuki, B. M.; Lee, S.-O.; Harris, K. D. M.; Kim, H.-S.; Do, K.-S.; Kim, K.- I. Cryst. Growth & Design 2002, 2, 309   DOI   ScienceOn
37 Holm, R. H.; Kennepohl, P.; Solomon, E. I. Chem. Rev. 1996, 96, 2239   DOI   ScienceOn
38 Kim, H.-S.; Park, H. J.; Oh, H. J.; Koh, Y. K.; Choi, J. H.; Lee, D.-H.; Cha, G. S.; Nam, H. Anal. Chem. 2000, 72, 4683   DOI   ScienceOn
39 Walsdorff, C.; Saak, W.; Pohl, S. J. Chem. Soc. Dalton Trans. 1997, 1857
40 Choi, J. H.; Koh, Y. K.; Kwon, I.-C.; Kim, H.-S.; Park, H. J.; Kim, S. J.; Cha, G. S.; Nam, H. Bull. Korean Chem. Soc. 1999, 20, 581
41 Stack, T. D. P.; Holm, R. H. J. Am. Chem. Soc. 1987, 109, 2546   DOI
42 Hiraoka, S.; Yi, T.; Shiro, M.; Shinonoya, M. J. Am. Chem. Soc. 2002, 124, 14510   DOI   ScienceOn
43 Reddy, P. J.; Ravichandran, V.; Chacko, K. K.; Weber, E.; Saenger, W. Acta Cryst. 1989, C45, 1871
44 Gozzo, F. C.; Eberlin, M. N. J. Org. Chem. 1999, 64, 2188   DOI   ScienceOn
45 Fielding, L. Tetrahedron 2000, 56, 6151   DOI   ScienceOn
46 Hynes, M. J. J. Chem. Soc. Dalton Trans. 1993, 311
47 Gadzekpo, V. P. Y.; Christian, G. D. Anal. Chim. Acta 1984, 164, 279   DOI   ScienceOn
48 Buck, R. P.; Lindner, E. Pure Appl. Chem. 1994, 66, 2527   DOI   ScienceOn
49 Umezawa, Y.; Umezawa, K.; Sato, H. Pure Appl. Chem. 1995, 67, 507   DOI   ScienceOn
50 Kim, S. H.; Youn, N. J.; Park, J. Y.; Choi, M. G.; Chang, S.-K. Bull. Korean Chem. Soc. 2006, 27, 1553   DOI   ScienceOn
51 Choi, H. J.; Park, Y. S.; Yun, S. H.; Kim, H.-S.; Cho, C. S.; Ko, K.; Ahn, K. H. Org. Lett. 2002, 4, 795   DOI   ScienceOn
52 Connors, K. A. Binding Constants; Wiley: New York, 1987
53 Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541
54 Kim, H.-S.; Choi, J. H.; Koh, Y. K.; Choi, H.-J.; Park, H. J.; Cha, G. S.; Nam, H. J. Inclusion Phenom. 2001, 40, 265   DOI   ScienceOn