由於液晶分子的物理特性，例如：光、電、磁等異方性，使其具有不同的應用價值，目前在生活中的應用最為人所知的即顯示器等商品。由於液晶分子可透過官能基的修飾，進而影響其物理性質，故引起許多合成化學家的研究興趣。本實驗即為合成出具有dioxole銜接 dove-tail alkyl chain官能基的化合物並改變alkyl chain的長度來探討其排列。由實驗結果推測:可能為螺旋狀的堆疊方式，具有優異的電子傳導性，於光電材料方面有良好的應用潛力。

Because of the unique physical properties of liquid crystal molecules, such as: light, electricity, magnetic anisotropy, they exhibit different values, the most known current application on displays in our life. As the liquid crystal molecules can be modified through the functional groups, thereby affecting its physical properties, it caused great interests in synthetic chemists. In this thesis, we synthesized liquid crystal based on dibezo[a,c]phenazine core and the dioxole skeleton was also induced into dove-tail alkyl chain functional group surrounding the central aromatic core . Moreover, we also change the chain length of alkyl chain to explore stacking arrangement structure of the mesophase. By the various instruments to explore the nature of stacking, we preliminary assumed that the mesophase might exhibit the helical stacking with excellent charge mobility, which could be good candidates for optical and electrical applications.

第一章 緒論..........................................................................................1
1-1 前言..............................................................................................1
1-2 螺旋超分子的種類及形成方法..................................................1
1-2.1 芳香環與芳香環之間的作用力.....................................2
1-2.2 分子間的氫鍵作用力....................................................20
1-3文獻回顧.....................................................................................22

第二章 實驗部份.............................................................................23
2-1 研究動機....................................................................................23
2-2 研究策略....................................................................................23
2-3 實驗流程與討論........................................................................24
2-3.1 製備2,2-dialkyl-benzo[1,3]dioxole-5,6-diamine.............24
2-3.2 製備2,3,6,7-Tetrakis-decyloxy-
phenanthrene-9,10-diones.................................................31
2-3.3 合成2,2-dialkyl-benzo[1,3]dioxole-5,6-diamine-
7,8,11,12-tetrakis-alkyloxy-dibenzo[a,c]phenazine.........35
2-4 文獻回顧....................................................................................37

第三章 物性檢測與探討..............................................................38
3-1檢測與分析.................................................................................38
3-2物性的討論.................................................................................41
3-2.1 系列A－【di-functionalized system】...........................41
3-2.2 系列B－【tri-functionalized system】...........................65

第四章 結論........................................................................................72

附錄........................................................................................................73
ㄧ、藥品與溶劑..........................................................................73
二、儀器設備...............................................................................73
三、化合物合成條件與檢測資料...............................................75
四、參考文獻..............................................................................92

1-3 文獻回顧(page 22)
1.Bushby, R. J.; Boden, N.; Kilner, C. A.; Lozman, O. R.; Lu, Z. B.; Liu, Q. Y.; Thornton-Pett, M. A. , J. Mater.Chem. 2003, 13, 470-474.
2.Gallivan, J. P.; Schuster, G. B. J. Org. Chem. 1995, 60, 2423-2429.
3.Brunsveld, L.; Folmer,B. J. B.; Meijer,E. W.; Sijbesma, R.P., Chem. Rev. 2001, 101, 4071-4097.
4.Yamamoto, T.; Fukushima, T.; Kosaka, A.; Jin, W.; Yamamoto, Y.; Ishii, N.; Aida, T. Angew. Chem.,Int. Ed. 2008, 47, 1672-1675.
5.Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am.Chem. Soc.1998, 120, 1944-1944.
6.Vyklicky, L.; Eichhorn, S. H.; Katz, T. J. Chem. Mater. 2003, 15, 3594-3601
2-4文獻回顧(page 37)
1.Pisula, W.; Kastler, M.; Wasserfallen, D.; Pakula, T.; Mullen, K. J. Am. Chem. Soc., 1992, 120, 448-449.
2.Harding, K. E.; May, L. M.; Dick, K. F. J. Org. Chem., 1975, 40, 1664-1665.
3.Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc.,1980, 102, 3056-3062.
4.國立中山大學化學研究所中華民國九十三年七月黃晟偉之碩士論文.
5.Antonisse, M. M. G.; Snellink-Ruël, B. H. M.; Yigit, I.; Engbersen, J. F. J.; Reinhoudt, D. N. , J. Org. Chem., 1997, 62, 9034.
6.Zhou, Z. L.; Weber, E.; Keana, J. F. W. , Tetrahedron Lett., 1995, 36, 7583.
7.Mohr, B.; Enkelmann, V.; Wegner, G., J. Org. Chem.,1994, 59, 635.
8.Halton, B.; Maidment, A. I.; Officer, D. L.; Warnes, J. M. , Aust. J. Chem., 1984, 37, 2119.
附錄參考文獻(page 92)
1. Pisula, W.; Kastler, M.; Wasserfallen, D.; Pakula, T.; Mullen, K. J. Am. Chem. Soc., 1992, 120, 448-449.
2. Magnus, P.; Fielding, M. R., Tetrahedron Lett., 2001,42, 6633 – 6636
3. Sugandhi, E. W.; Falkinham, J. O.; Gandour, R. D., Bioorg. Med. Chem., 2007,15, 3842 – 3853.
4. Harding, K. E.; May, L. M.; Dick, K. F. J. Org. Chem., 1975, 40, 1664-1665.
5. Matsuo, J.; Iida, D.; Yamanaka, H.; Mukaiyama, T., Tetrahedron, 2003, 59, 6739-6750.
6. Nightingale, D. V.; Turley, R. H. J. Org. Chem., 1961, 26, 2656-2658.
7. Davis, R.; Schultz,H. P., J. Org. Chem., 1962, 27,854-857.
8. Shirley, D. A.; Schmidt, G. A., J. Am. Chem. Soc., 1951, 73, 5493;
9. Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc.,1980, 102, 3056-3062.
10. Napolitano, E.; Fiaschi, R.; Mastrorilli, E., Sythesis, 1986, 1, 122-125
11. Silox Yoder, C.M.; Zuckerman, J.J., J. Hetero.Chem.1967, 4, 166,167
12. McKeown, N. B.; Helliwell, M.; Hassan, B. M.; Hayhurst, D.; Li, H.; Thompson, N.; Teat, S. J., Chem. Eur. J., 2007,13,228 – 234.
13. Cole, E. R.; Crank, G.; Minh, H. T. H., Aust. J. Chem., 1980, 33, 675 – 680.
14. Takakis, I. M.; Hadjimihalakis, P. M.; Tsantali, G. G.; Pilini, H., J. Hetero. Chem. 1992, 29, 123 - 128