本研究乃利用薁類分子的雙極特性及在1、3位置帶有較多負電荷易進行親核取代反應的特性，以合成含苯環參鍵的液晶化合物。
本研究主要可分為三個部分：
（一）先以二環戊二烯製備起始物2-對甲苯磺醯氧□酮，再以乙醛合
成薁-1-羧酸甲酯，最後3以NBS溴化，製成3-溴化薁-1-羧酸甲
酯。
（二）以1-溴-4-烷基苯和1-碘基-4-烷氧基-苯以Sonogashira耦合反
應接上乙炔基之後，再以retro-Favorsky的方法除去保護基。
（三）將前兩部分合成的化合物在3位置再以Sonogashira耦合反應合
成4個1-羧酸甲酯-3-（4-烷基-苯乙炔基）-薁（1-methyl-
carboxylate-3-(4-propyl-phenylethenyl)-azulene）與15個
1-羧酸甲酯-3-（4-烷氧基-苯乙炔基）-薁（1-methyl-
carboxylate-3-(4-pentyloxy-phenylethynyl)–azulene）共
19個新化合物。

The research was synthesized 1、3 position derivatives of azulene containing ethynal group and benzene ring.We attempted to study the influence of the dipole properties in liquid crystal materials.
We have synthesized starting material--methyl 3-bromoa-
zulene-1-carboxylate followed the Rnown Nozoe methods.And a series of 1-ethynyl-4-n-alkyl-benzene and 1-ethynyl-4-n-
alkyloxy-benzene by Sonogashira coupling reaction and deprotective.
Finally we used Sonogashira coupling reaction again of two previous materials to accomplish four new conpounds of 1-methyl-carboxylate-3-(4-n-alkyl-phenylethenyl)-azulene and fifteen new conpounds of 1-methyl-carboxylate-3-(4-n-
alkyloxy-phenylethynyl)–azulene.

參考文獻
1. T.Morita,K.Takase and M.Kaneko,Jpn.Pat.0269438,1990.
2. R.Brettle,D.A.Dunmur,S.E.Estdale and C.M.Marson,
J.Mater.Chem.,1993,3,327.
3. S.E.Estdale,R.Brettle,D.A.Dummer and C.M.Marson,
J.Mater.Chem.,1997,7(3),391.
4. T.Morita,K.Takase and M.Kaneko,Jpn.Pat.0269436,1990.
5. T.Morita,K.Takase and M.Kaneko,Jpn.Pat.0269437,1990.
6. T.Morita,K.Takase and M.Kaneko,Jpn.Pat.0269439,1990.
7. T.Morita,K.Takase and M.Kaneko,Jpn.Pat.3261753,1991.
8. T.Morita,K.Takase and M.Kaneko,Jpn.Pat.3261754,1991.
9. T.Morita,K.Takase and M.Kaneko,Jpn.Pat.0269441,1990.
10. S.Ito,H.Inabe,N.Morita,K.Ohta,T.Kitaamura and K.Imafuku,
J.Am.Chem.Soc.2003,125,1669.
11.簡思源, 碩士論文（交通大學）,2001.
12. 徐國峰,碩士論文（交通大學）,1998.
13. M.Yasunami,S.Mitoshi,N.Kanegae and K.Takase,Bull.Chem.
Soc.Jpn.,1993,66,892.
14. A.G.Anderson,J.A.Nelson and J.Tazuma,J.Amer.Chem.Soc.,
1953,75,4980.
15.R.N.McDonald,R.R.Reitz,and J.M.Richmond,J.Org.Chem.,
1976,41,10,1822.
16. K.Sonogashira,Y.Tohda and N.Hagihara,Tetrahedron Letter,
1975,50,4467.
17. R.D.Stephens and C.E.Castro,J.Org.Chem.,1963,28.3313.
18. R.M.Silverstein,G.C.Bassler,and T.C.Morrill,
Spectrometric Identification of Organic Chemistry,20,歐
亞書局,1991.
19. J.F.E.McOmie,Protective Group in Organic Chemistry,7,國
興出版社,民國64年.
20. T.Nozoe,S.Seto,S.Matsumura and Y.Murase,Bull.Chem.Soc.
Jpn.,1962,35(7),1179.
21. S.Thorand and N.Krause,J.Org.Chem.,1998,63,8551.
22. M.W.Miller and C.R.Johnson,J.Org.Chem.,1997,62,1582.
23. T.Hundertmark,A.F.Littke,S.L.Buchwald and G.C.Fu,
Ore.Lett.,2000,2(12),1729.
24. A.Mori,M.S.Mohamed Ahmed,A.Sekiguchi,K.Masui and
T.Koike,Chemistry Letter,2002,756.
25. Y.Ma,C.Song,W.Jiang,Q.Wu,Y.Wang,X.Liu,and M.B.Andrus,
Organic Letters,2003,5(18),3317.