本研究希望研究薁類特有的雙極性如何影響薁類在金表面形成自組裝單層薄膜，並嘗試找出薁類在金表面上形成薄膜時的排列情形。有別於前人使用二-3-甲基-薁基亞甲基二硫化物形成薄膜，我們試著合成化合物二-1-薁基二硫化物以避免其在金表面做自組裝單層薄膜時排列時受到CH2的鍵角影響，希望能更直接地看到其表面的排列情
形。
我們從化合物草酚酮開始合成薁類的中間產物2-氧-2-氫-環庚〔b〕呋喃-3-羧酸甲酯. 再將2-氧-2-氫-環庚〔b〕呋喃-3-羧酸甲酯與乙醛、二乙胺 (diethylamine)反應形成化合物甲基-薁-1-羧酸. 再將甲基-薁-1-羧酸在乙醇的環境下與氫氧化鉀與鹽酸反應形成薁-1-羧酸.。再將薁-1-羧酸與三氯乙酸(trichloroacetic acid)反應形成薁。 最後，參考Anderson 的方法來將薁合成為化合物二-1-薁基二硫化物，並根據Inorganic Chemistry Synthises 所記載的方法改進增加合成硫化氰(Thiocyanogen) 並將溶劑由四氯化碳改成二氯甲烷成功的合成了二-1-薁基二硫化物並使用質譜儀、紅外線光譜儀與核磁共
振儀來鑑定化合物.
在觀測儀器的形式，將修正反射式FTIR看SAM的方式，企圖在未來能使用高解析STM及NEXAFS來更直接地觀察薁類在金表面的排列情形。

In this examination we are interesting in the dipolar effect of azulene to form self-assembled monolayer on gold surfaces. We try to understand how the film arranged on gold surfaces under the effect of the dipolar property of azulene.Different to the structure of di-(3-methyl-azulyl methenyl) difulfide, we try to use di-1-azulyl disulfide to avoid the influence of the methlene’s bond angle on the arrangement on the gold
surfaces.
We start with tropolone to synthesize the intermediate of azulene, methyl-2-oxo-2H-cyclohepta〔b〕furan-3-carboxylate. The intermediate has been reacted with diethylamine and acetaldehyde to accomplish Methy azulene-1-carboxylate. Methy azulene-1-carboxylate has been reacted with potassium hydroxide in ethanol and treated with hydrochloric acid to accomplish azulene-1-carboxylic-acid. Azulene-1-carboxylic-acid has been reacted with trichloroacetic acid to accomplish azulene. Finally,we have synthesized di-1-azulyl disulfide from azulene and thiocyanogen,and identified the compound by using mass spectrometry、infrared spectrometry and nuclear magneticresonance spectrometry.
In the way of observational instruments, we attempt to modify the way to see the SAM from reflection FTIR to high-resolution STM and NEXAFS to take more directly data of the structure of azulenearranged on the gold in
the future.

1. Ulman, A. ,Chem.Rev. 1996, 96, 1533.
2. Bigelow, W.C.; Pickett,D.L.;Zisman, W.A., J. Collid Interface Sci., 1946, 1, 513.
3. Nuzzo R.G., Allara D.L.,J. Am. Chem. Soc.,1983,105,4481.
4. Ulman,A.,An introduction to Ultrathin Organic Films,Form Langmuir-Blodgett to Self-Assembly;Academic Press:Boston,1991.
5. Lee, K.B.; Park, S.J., C. A. Mirkin, J. C. Smith, M. Mrksich, Science,2002, 295, 1702.
6. 許適恆,碩士論文,國立臺灣科技大學化學工程系,2008.
7. Lee,W.,Oh,B.K.,Bao,Y.M.,Paek S.H.,Lee,W.H.,Choi,J.C.,
Biosensors & Bioelectronics,2003,19,185-192.
8. Allara,D.L. ;Nuzzo,R.G. ,Langmuir,1985, 1,45.
9. Schlotter,N.E. ;Porter, M.D. ; Bright, T.B. ; Allara, D.L., Chem.Phys. Lett. 1986,132,93.
10. Tao, Y.T.,J.Am.Chem. Soc. ,1993,115,4350.
11. Samant, M.G. ; Brown, C.A., Langmuir ,1993,9,1082.
12. Chau, L. K.;Porter, M. D., Chem. Phys. Lett. ,1990,167,198-204.
13. 陶雨台, 自然科學簡訊,第十五卷第二期, 2003, 32.
14. Tao, Y. T.;Lin ,W. L.,J. Phys. Chem. B,1997,101,9732.
15. 柯明珊,碩士論文,國立新竹教育大學數理研究所(自然組),2003.
16. 林彥光,碩士論文,國立新竹教育大學自然教育學系碩士班,2005.
17. 向孟娟,碩士論文,國立新竹教育大學自然教育學系碩士班,2004.
18. 王慧娟,碩士論文,國立新竹教育大學自然教育學系碩士班,2008.
19. 彭士峯,碩士論文,國立新竹教育大學應用科學系碩士班,2010
20. 涂明顯,碩士論文,國立清華大學化學系,2002.
21. Colin D.B.;Troughton E.B.;Tao Y. T.;Evall J.;Whitesides G.M.;Nuzzo R.G.,J. Am. Chem. Soc.,1989,111,321.
22. Tao,Y. T.,J. Am. Chem. Soc.,1993,115,4350.
23. Lauterbur P.C.,J. Am. Chem. Soc.,1961,83,1838.
24. Yasunami M.;Miyoshi S.;Kanegae N.;Tadase K.,Bull. Chem. Soc. Jpn.
,1993,66,892.
25. Nozoe T.;Seto S.;Mastsumura S.;Murase Y.,Bull. Chem. Soc. Jpn.,
1962,35,1179.
26. Wang F.;Lai Y. H.;Kocherinsky N. M.;Kosteski Y. Y.,Org. Lett.,
2003,5,995.
27. 游瑞成,有機光譜學,徐氏基金會出版,1998.
28. Anderson, Jr.; Richard N. M.,J. Am. Chem. Soc., 1959,81, 5669-5674
29. Silverstein,R.M.,Webster,F.X.,Kiemle,D.J.,SPECTROMETRIC IDENTIFICATION OH ORGANIC COMPOUNDS(7ed),2005.
30. Schumann, H.,J. Chem. Soc.,Dalton Trans.,2000,3885-3896.
31. Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D.,
J. Am. Chem. Soc.,2002,124,10887.
32. Hobza, P.; Selzle, H. L.; Schlag, E. W.,Chem. Rev.,1994,94,1767
33. Dou, R.F.; Ma, X.C.; Xi, L.; Yip, H. L.; Wong, K.Y.; Lau, W. M. ; Jia, J.F.; Xue, Q.K.; Yang, W.S.; Ma, H.;Alex K-Y. Jen, Langmuir,2006,22,3049.
34. Luhiwy, R.; Keehn, P. M., J. Am. Chem. Soc.,1977,99,3797.
35. Koenig T.; Rudolf K.; Chadwick R.; Geiselmann H.; Patapoff T.; Klopfenstein C. E., J. Am. Chem. Soc.,1986,108,5024.
36. 扈蔚山,碩士論文,國立清華大學化學系,2002.