本實驗室在過去兩年成功的開發出新的苯駢[k]螢蒽合成途徑，在醋酸鈀催化和醋酸銀活化的系統下，能將雙炔化合物和鄰二碘苯衍生物反應生成以苯駢[k]螢蒽為基本結構的線性多駢苯化合物，並可導入多種官能基及芳香環系統。本論文中以延伸上述合成方法並嘗試以鉬金屬催化歧化反應進行聚合。
　　雙炔化合物由1,8二碘萘 (40)經由薗頭耦合1 (Sonogashira Coupling)導入不同的含有鹵素的芳香族化合物，並在芳香環上或鄰二碘苯衍生物上導入六到八個碳的烷鏈官能基以改善產物的溶解度。並使用根岸耦合2 (Negishi coupling)將芳香環上的鹵素取代為1丙炔，形成以苯駢[k]螢蒽為基本結構的雙炔衍生物。
　　目前我們已經成功的製備出9.10-二辛氧基-7.12-雙(4-(1-丙炔基)苯基)苯駢[k]螢蒽(36ab)、7.12-雙(2.5-二辛氧基-4-(1-丙炔基)苯基)苯駢[k]螢蒽(36bc)和7.12-雙(9.9-二己基-7-(1-丙炔基)芴基)-9.10-二甲氧基苯駢[k]螢蒽(36ca)等三種苯駢[k]螢蒽的雙炔衍生物為單體，並已成功的藉由非環狀雙炔歧化反應 (Acyclic diyne metathesis reaction)得到兩種聚合物。
　　關於此類聚合物的光電及材料等性質研究，未來將會陸續進行。

For last two years, we founded a new method to synthesize Benzo[k]fluoranthene-based linear acenes successfully. This new synthetic design is different from the conventional methods that always undergo the Diels-Alder reaction. Our protocol is in the presence of palladium catalyst and the optimized conditions, we can get the 1,8-diethynylnaphthalene derivatives and aryl iodides undergo the cycloadditions to get the Benzo[k]fluoranthene derivatives. This protocol has highly functional group tolerance and excellent yield. We can also extend aromatic systems easily by this method. Our protocol is simpler and more efficient than conventional ones, and now is trying to extend the usage of this protocol.
We tried to introduce different aromatic rings into the benzo[k]fluoranthene derivatives, keeping a bromind on the additional aryl groups of benzo[k]fluoranthene derivatives, substituting the bromide into 1-propyne by Negishi coupling to get the benzo[k]fluoranthene derivative monomers. Then, we use the MortreuxBunz catalyst system to have the Benzo[k]fluoranthene derivative monomers undergo the acyclic diyne metathesis reaction to obtain the benzo[k]fluoranthene- based polymer derivatives.
Presently, we already generated three kinds of benzo[k]fluoranthene derivative monomers, and get two kinds of benzo[k]fluoranthene-based polymer derivatives by using acyclic diyne metathesis reaction.
About the photophysical and electrochemical properties of these polymers will be determined in the future.

1.Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett., 1975, 4467.
2.Negishi, E.; King, A. O.; Okukado, Nobuhisa. J. Org. Chem. 1977, 42, 1821.
3.Pope, M.; Kallmann, H. P.; Magnante, P. J. Chem. Phys. 1963, 38, 2042.
4.VanSlyke, S. A.; Tang, C. W. Appl. Phys. Lett. 1987, 51, 913.
5.Knight, A. W.; Greenway, G. M. Analyst. 1994, 119, 879.
6.Synthesis of benzo[k]fluoranthene in solution phases: (a) Whitlock, H. W., Jr. J. Org. Chem. 1964, 29, 3129. (b) Mouri, M.; Kuroda, S.; Oda, M.; Miyatake, R.; Kyogoku, M. Tetrahedron 2003, 59, 801. (c) Rice, J. E.; Cai, Zhen-Wei; J. Org. Chem. 1993, 58, 1415. (d) Panda, K.; Venkatesh, C.; Ila, H.; Junjappa, H. Eur. J. Org. Chem. 2005, 2045. (e) Stuparu, M.; lentz, D.; Rueegger, H.; Schlueter, A. D. Eur. J. Org. Chem. 2007, 88.
7.(a) Fabrizio, E. F.; Prieto, I.; Bard, A. J. J. Am. Chem. Soc. 2000, 122, 4996. (b) Branchi, B.; Balzani, V.; Ceroni, P.; Kuchenbrandt, M. C.; Klärner, F. G.; Bläser, D.; Boese, R. J. Org. Chem. 2008, 73, 5839. (c) Yan, Q.; Zhou, Y.; Ni, B. B.; Ma, Y.; Wang, J.; Pei, J.; Cao, Y. J. Org. Chem. 2008, 73, 5328.
8.Debad, J. D.; Morris, J. C.; Lynch, V.; Magnus, P.; Bard, A. J. J. Am. Chem. Soc. 1996, 118, 2374.
9.(a) Bergmann, E. J. Am. Chem. Soc. 1952, 74, 1075. (b) Bergmann, E. Nature, 1948, 161, 889.
10.Allen, C. F. H.; Vanallan, J. A. J. Org. Chem., 1952, 17, 845.
11.Kung, Y.-H.; Cheng, Y.-S.; Tai, C.-C.; Liu, W.-S.; Shin, C.-C.; Ma, C.-C.; Tsai, Y.-C.; Wu, T.-C.; Kuo, M.-Y.; Wu. Y.-T. Chem. Eur. J. 2010, 16, 5909.
12.Burroughes, J. H.; Bradley, D. C. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend,R.H.; Burns, P. L.; Holmes, A. B. Nature , 1990, 347, 539.
13.Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. 1998,37, 402.
14.Hide, F.; Diaz-Garcia, M. A.; Schwartz, B. J.; Heeger, A. J. Acc.Chem. Res. 1997, 30, 430.
15.Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
16.Ball, P. Made to Measure: New Materials for the 21st Century; Princeton University Press: Princeton, NJ, 1997.
17.Giesa, R. and R.C. Schulz. Makromol Chem. Phys. 1990, 191, 857.
18.Pschirer, N. G.; Bunz, U. H. F. Macromolecules 2000, 33, 3961.
19.Holzer, W.; Penzkofer, A.; Pichlmaier, M.; Bradley, D. D. C.; Blau, W. J. Chem. Phys. 1999, 248, 284.
20.Moroni, M.; Lemoigne, J.; Luzzati, S. Macromolecules 1994, 27, 562.
21.Swager, T.M.; C.J. Gil; Wrighton, M.S. J. Phys. Chem. 1995, 99, 4886.
22.Schrock, R. R.; Clark, D. N.; Sancho, J.; Wengrovius, J. H.; Pederson, S. F. Organometallics 1982, 1, 1645.
23.Weiss, K.; Michel, A.; Auth, E. M.; Bunz, U. H. F.; Mangel, T.; Mullen, K. Angew. Chem. 1997, 36, 506.
24.(a) Kloppenburg, L.; Song, D.; Bunz, U.H.F. J. Am. Chem. Soc. 1998, 120, 7973. (b) Mortreux, A.; Blanchard, M. Chem. Commun. 1974, 786. (c) Kaneta, N.; Hikichi, K.; Asaka, S.; Uemura, M.; Mori, M. Chem. Lett. 1995, 1055.
25.Bunz, U.H.F. Acc. Chem. Res. 2001, 34, 998.
26.Hsieh, J.-C.; Cheng, C.-H. Chem.Commun., 2008, 2992
27.Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481.
28.Sluch, M. I.; Godt, A.; Bunz, U. H. F.; Berg, M. A. J. Am. Chem. Soc. 2001, 123, 6447.
29.Staab, H.A.; Ipaktschi, J. Chemische Berichte 1971, 104, 1170.
30.Yamamoto, Y.; Gridnev, I. D.; Patil, N. T.; Jin, T. Chem. Commun. 2009, 5075.
31.Sosnowski, M.; Skulski, L. Molecules 2005, 10, 401.
32.Ong, C. W.; Liao, S.-C.; Chang, T.-H.; Hsu, H.-F. J. Org. Chem. 2004, 69, 3181.
33.Du, Z.-T.; Liu, R.; Wang, J.-R.; Li, A.-P. Molecules 2009, 14, 2111.
34.Egbe, D. A,; Carbonnier, B.; Ding, L. M.; Muhlbacher, D.; Birckner, E.; Pakula, T.; Karasz, K. E.; Grummt, U. W. Macromolecules 2004, 37, 7451.
35.Promarak, V.; Punkvuang, A.; Sudyoadsuk, T.; Jungsuttiwong, S.; Saengsuwan, S.; Keawin, T.; Sirithip, K. Tetrahedron 2007, 63, 8881.