中文摘要：
本研究是以Hruby和Stock的醯胺合成法研發出一系列不同環數的含硫大環冠狀二醯胺化合物，利用萃取及傳輸實驗對銅(II)離子的錯合能力進行探討。
我們以此系列化合物做為對過渡金屬離子錯合的配位子，在混合各種離子的傳輸實驗(pH=1.9)中，此酸性條件下對鈀(II)離子具有良好的抓取能力，比較之下對銅(II)離子則相差甚多，因此我們以氫氧化鈉調整在各種pH值下進行銅(II)離子的萃取及傳輸實驗，發現在偏中性環境(pH=6.8)下，含硫大環冠狀二醯胺化合物對銅(II)離子的萃取能力，傳輸速率均大幅地增加。
從傅氏紅外線光譜(FT-IR)及快速原子撞擊質譜(FAB-MS)分析的結果說明了此類化合物在偏中性環境下錯合時的去質子現象。可由此一現象來解釋pH值的不同對此一系列化合物與銅(II)離子錯合能力之影響。
除此之外，本實驗也利用了兩種電化學的方法來計算含硫大環冠狀二醯胺化合物對銅(II)離子在甲醇中的錯合穩定常數Ks值：在循環伏特安培法中使用二氧化錫導電玻璃為工作電極(working electrode)，鉑絲為輔助電極(counter electrode)，以銀絲為參考電極(reference electrode)，利用半波電位(E1/2) 與配位子濃度之對數的關係計算出Ks值；而電位滴定法是以此系列大環化合物滴定銅(II)離子，利用當量點後的電位來測得錯合穩定常數Ks值。測得此系列化合物對銅(II)離子之log Ks 約為4。

Abstract：
In this thesis , the series of macrocyclic diamides containing sulfur were synthesized according to a procedure reported. From solvent extraction and liquid membrane transport, they are used to study for the ability in complexation with copper ions
These compounds showed good ability in capturing Pd(II) at pH1.9. But it is hard to catch copper ions at this pH. We adjusted pH by NaOH to proceed the extaction and transport experiments for copper ions. Result shows these compounds develop their complexation ability more in near neutral situation (pH =6.8).
From FT-IR and fast atom bombardment mass spectrometry(FAB-MS), Deprotonation may occur from the amide group of these compounds. The Phenomenon can be explained the pH effect to copper ions.
Electrochemical analysis was used for caculating the stability constants(Ks) of these complexes. In which ITO were used as working electrode, Pt as counter electrode, and Ag as reference electrode. Stability constants are solved from the relation of E1/2 vs. logCL; Ks is estimated to be 104.

參考文獻：
1. Inoue, M. B.; Velazquez, E. F.; Medrano, F.; Ochoa, K. L.; Galvez, J. C.; Inoue, M.; Fernando, Q., Inorg. Chem. 1998, 37, 4070.
2. Bu, X. H.; An, D. L.; Zhang R. H.; Clifford, T.; Kimura, E., J. Chem. Soc., Dalton Trans., 1998, 2247.
3. Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoya, M.; Kimura, E., 1995, 2289.
4. Bu, X. H.; An, D. L.; Shionoya, M.; Kimura, E., Journal of Inclusion Phenomena and Molecular Recognition in Chemistry, 1997, 27, 245.
5. Lingane, J. J., Chem. Rev.,1941,29,1.
6. Buschmann, H. J., Inorganica Chimica Acta, 1992, 195, 51.
7. Yoshio, T.; Yasuo, O., J. Org. Chem., 1994, 59, 2967.
8. Jagessar, R. C.; Shang, M.; Scheidt, R.; Burns, D. H., J. Am. Chem. Soc. 1998, 120. 11684.
9. Kimura, E., Tetrahedron, 1992, 48, 6175.
10. Krakowiak, K. E. ; Bradshaw, J. S. ;Zamecka and Krakowia, D., J. Chem. Soc. Rev., 1989, 89, 929.
11. Dietrich, B.; Lehn, J. M.; Sawage, J. P.; Blanzat, J., Tetrahedron, 1973, 29, 1629.
12. Dietrich, B.; Sawage, J. P., Tetrahedron Lette. 1969, 2885.
13. Kimura, E., Kurogi, Y.; Tojo, T.; Shionoya, M and Shiro, M., J. Am. Chem. Soc., 1991, 113, 4857.
14. Barstow, L. E.; Hruby, U. J., J. Org. Chem., 1971, 36, 1305.
15. Stock, G; Morgans, D.J., J. Am. Chem. Soc., 1979, 101, 7110.
16. Liu, L. K.; Hsidh,T. P.; Kuo, S. M. Synthesis, 1994, 309.
17. Weber, e.; Toner, J. L.; Laidler, C. A. Stoddart, J. F. and Bartsch, R. A. Ed., "Crown Ethers and Analogs ", Wiley &Sone, New ,York , 1989.
18. Pederson, C. J., J. Am. Chem. Soc. 1970, 92, 386.
19. Frinsdorff, H. K., J.Am. Chem. Soc. 1971, 93, 600.
20. I zarr, R. M; Earough, D.J.; Christinsen, J., J. Chem. Rev. 1974, 74, 351.
21. Izatt, R. M.; Bradshaw, J. S.; Lamb, J. D., Chem. Rev., 1985, 85, 271.
22. Hruska, E; Petramek, J., Polymer Bulletin, 1987, 17, 103.
23. Kimura, E.; Dalimunte, C. A.; Yamashita, A.; Machida, R., J. Chem. Soc. Chem. Commun., 1985, 1041.
24. Kimura, E.; Kurogi, Y.; Wada, S.; Shionoya, M., J. Chem. Soc. Chem. Commum., 1989, 781.
25. Kimura. E.; Kurogi, Y.; Wada, S.; Shionoya, M., J. Chem. Soc. Chem. Commun., 1988,1166.
26. Kimura, E., Pure & Appl. Chem., 1989, 61, 823.
27. Bossu, F. P.; Chellappa, K. L.; Margerum, D. W., J. Am. Chem. Soc., 1977, 99, 2195.
28. Murray, S. G.; Hatley, F. R., Chem. Rev., 1981, 81, 365.
29. Kirvan, G. E.; Margerum, D. W., Inorg. Chem., 1985, 24, 3017.
30. Tsukube, H., J. Coord. Chem,. 1987, 16, 101.
31. Choy, E. M.; Evans, D. F.; Cussler, E. L., J. Am. Chem. Soc.,1974, 96, 7085.
32. Izatt, R. M, J. Pure & Appl. Chem., 1986, 58, 1453.
33. Wienk, M. M.; Stolwijk, T. B.; Sudholten, E. J. R.; Reinnadt, J., J. Am. Chem. Soc., 1989, 111, 798.
34. Lamb, J. D.; Christensen, J. J.; Izatt, S. R.; Bedke, K.; Astin, M.S. and Izatt, R. M., J. Am. Chem. Soc., 1980, 102, 3399.
35. Fredrick, L. A.; Fyles, T. M.; Malik-Diemer, V. A. and Whitfield, D. M., J. Chem. Soc. Chem. Commun., 1980, 1211.
36. Czech, B.; Kang, S. I.; Barsch, R. A., Tetrahedron Lett., 1983, 24, 457.
37. Nakatsuji, Y.; Kobayashi, H.; Okakara, H., J. Chem. Soc. Chem. Commun., 1983, 801.
38. Kimura, E.; Sakamoto, H.; Yoshinage, M.; Shono, T., J. Chem. Soc. Chem. Commun., 1983, 978.
39. Izatt, S. R.; Hawkins, R. T.; Christensen, J. J.; Izatt, R. M., J. Am. Chem. Soc., 1985, 107, 63.
40. Frederick, Laurel A.; Fyles, Thomas M.*; Malik-Diemer, Virginia A.; Whitfield, Dennis M., J. C. S. Chem. Commum., 1980, 1211.
41. Kimura, K, J. Chem. Soc., Chem. Commun., 1983, p.978.
42. Storrier, G. D.; Takada, K.; Abruna, H. D., Inorg. Chem., 1999, 38, 559.
43. Kersting, B, Eur. J. Inorg. Chem., 1998, 1071.
44. Ebadi, M.; Lever, A. B. P., Inorg. Chem., 1999, 38, 467.
45. Yokoyama, K.; Kayanuma, Y., Anal. Chem., 1998, 70. 3368.
46. Brust, M.; Blass, P. M.; Bard, A. J., Langmuir, 1997, 13, 5602.
47. Xie, B., Inorg. Chem., 1999, 38, 12.
48. Domenech, A., Inorganica Chimica Acta 252, 1996, 123.
49. Di Bilio, Angel J., J. Am. Chem. Soc., 1997, 119, 9921.
50. Tomaszewski, L.; Lagger, G.; H, Hubert G., Anal. Chem., 1999, 71, 837.
51. Bazzicalupi, C., J. Chem. Soc., Daltoon Trans., 1999, 393.
52. Skoog, D.; West, D. M.;Holler, F. J., Analytical Chemistry.
53. Kimura, E; Dalimunte, C. A.; Yamashita, A.; Machida, R., J. Chem. Soc., Chem. Commun., 1985, p. 1041.