中文摘要
本研究希望利用薁類的雙極特性，合成分子間具有偶極-偶極吸引力的3位置、4位置不同碳鏈的羧酸薁類化合物，以作為吸附在銀表面的有機自組裝單層薄膜材料。

第一部先以8-甲氧羰基-2-酮-2H-環庚﹝b﹞呋喃-3-羧酸甲酯為起始物，與長鏈溴烷反應，合成4位置分別接兩種不同碳鏈的化合物：8-壬烷氧-2-羰基-2H-環庚﹝b﹞呋喃-3-羧酸甲酯(D)及8-十七烷氧-2-羰基-2H-環庚﹝b﹞呋喃-3-羧酸甲酯(E)。
再利用正十二醛及正二十醛與1,4-氧氮陸圜先形成烯胺類，與上述合成之化合物進行﹝8+2﹞環加成反應，生成在3位置，4位置不同長短碳鏈的3-烷基-4-烷氧基-1-薁類羧酸甲酯化合物，最後再經水解，合成四個3、4位置分別為短-短、短-長、長-短、長-長，最終產物3-烷基-4-烷氧基-1-薁類羧酸化合物。
之後，擬以合成的3-烷基-4-烷氧基-1-薁類羧酸甲酯化合物為原料，吸附在銀表面形成自組裝單層薄膜，利用原子力顯微鏡、反射式紅外線光譜分析薄膜結構，作為判斷薄膜的排列情形是否因薁類的偶極-偶極作用力呈現均勻相的分布？

Abstract
We try to synthesize 3-Alkyl-4-Alkoxy-azulene-1-carboxylic Acids for the material of self-assembled monolayer on the silver surface according to the influence of dipolar property of azulenes. In addition of van der Weals force , it may be show a different phenomenon of self-assembled monolayer on the silver surface, corresponding to the usual alkyl and aromatic ring compounds chain.

The reaction of staring material, Methyl 8-hydroxy-2-oxo-2H-cyclohepta﹝b﹞furan-3-carboxylate (C) has been reacted with 1-Bromononane and 1-Bromoheptadecane to accomplished Methyl 8-nonoxy-2-oxo-2H-cyclohepta﹝b﹞furan-3-carboxylate (D) and Methyl 8-heptadecoxy-2-oxo-2H-cyclohepta﹝b﹞furan-3-carboxylate (E). The two different carbon length intermediate has been reacted again with two different carbon length aldehydes and morpholine to formed four different 3-alkyl-4alkoxy-1-carboxylate(F、G、H、I) .

Finally the one azulene carboxylic acid (3-Decyl-4-nonyloxy-azulene-1-carboxylic acid J) were obtained by hydrolysis successfully.

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