在本論文第一部份中主要探討開發合成寡聚噻吩衍生物的新方法，
其結合了以鈀金屬催化的碳碳鍵偶和的方式，可以簡單的合成出寡
聚噻吩衍生物。先以Suzuki coupling 及Negishi coupling 合成出一系
列芳香環或芳香雜環取代的乙烯基噻吩化合物，最後則是以Negishi
coupling 將其與雙溴取代噻吩衍生物作連結，合成出一系列的寡聚噻
吩。並以電化學及吸放光光譜鑑定其物理性質，由電化學的結果顯示
此一系列寡聚噻吩的HOMO 接近5.1 eV，適合應用於p 型有機場效
電晶體。
第二部份則是測定一系列多環芳香烴化合物的電化學性質，包括
苯并[1,2-c:3,4-c′:5,6-c′′]三噻吩衍生物、苯并[k]熒蒽衍生物及多取代
8,8a-二氫環戊烯[a]茚。藉由測定出的氧化還原電位，探討了結構與
氧化還原的關係。

In this article, the first part is focused on a new synthetic method for oligothiophenes. At first, the aryl- or heteroaryl-vinylthiophenes were synthesized by Suzuki coupling or Negishi coupling. Then, those intermediates were reacted with a series of dibromothiophene core by twice
Negishi coupling for these oligothiophene derivatives. Those oligothiophenes were characterized carefully by electrochemical and optical spectroscopic methods (UV/Vis and photoluminescence spectra). According to the
electrochemical data, the HOMO level of this series of oligothiophenes was near 5.1 eV and exhibits the possibility for applying in p-type OFET (organic
field-effect transistor).

In the second part, a series of PAHs (benzo[1,2-c:3,4-c′:5,6-c′′]trithiophene derivatives, benzo[k]fluoranthene-based linear acenes and highly substituted 8,8a-dihydrocyclopenta[a]indenes) were characterized by
electrochemical method. According to the electrochemical data, the relationship between molecular structure and redox potential was well discussed.

(1) Yang, Y.; Wudl, F. Adv. Mater. 2009, 21, 1401.
(2) Roncali, J. Chem. Rev. 1997, 97, 173.
(3) Watson, M. D.; Fechtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267.
(4) Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Chem. Rev. 2009, 109, 897.
(5) Skotheim, T. A.; Reynolds, J. R. Handbook of conducting polymers; 3rd ed.; CRC: Boca Raton, 2007; Vol. 2.
(6) Wang, L. X.; Li, X. G.; Yang, Y. L. React. Funct. Polym. 2001, 47, 125.
(7) Mishra, A.; Ma, C. Q.; Bauerle, P. Chem. Rev. 2009, 109, 1141.
(8) Cheng, Y. J.; Yang, S. H.; Hsu, C. S. Chem. Rev. 2009, 109, 5868.
(9) Baumgartner, T.; Reau, R. Chem. Rev. 2006, 106, 4681.
(10) Tour, J. M. Chem. Rev. 1996, 96, 537.
(11) Takahashi, M.; Masui, K.; Sekiguchi, H.; Kobayashi, N.; Mori, A.; Funahashi, M.; Tamaoki, N. J. Am. Chem. Soc. 2006, 128, 10930.
(12) Lukevics, E.; Arsenyan, P.; Pudova, O. Heterocycles 2003, 60, 663.
(13) Anthony, J. E. Angew. Chem. Int. Edit. 2008, 47, 452.
(14) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
(15) Mas-Torrent, M.; Rovira, C. Chem. Soc. Rev. 2008, 37, 827.
(16) Kudo, K.; Yamashina, M.; Moriizumi, T. Jpn. J. Appl. Phys. Part 1 - Regul. Pap. Short Notes Rev. Pap. 1984, 23, 130.
(17) Ebisawa, F.; Kurokawa, T.; Nara, S. J. Appl. Phys. 1983, 54, 3255.
(18) Tsumura, A.; Koezuka, H.; Ando, T. Appl. Phys. Lett. 1986, 49, 1210.
(19) Horowitz, G.; Fichou, D.; Peng, X. Z.; Xu, Z. G.; Garnier, F. Solid State Commun. 1989, 72, 381.
(20) McCulloch, I.; Heeney, M.; Chabinyc, M. L.; DeLongchamp, D.; Kline, R. J.; Coelle, M.; Duffy, W.; Fischer, D.; Gundlach, D.; Hamadani, B.; Hamilton, R.; Richter, L.; Salleo, A.; Shkunov, M.; Sporrowe, D.; Tierney, S.; Zhong, W. Adv. Mater. 2009, 21, 1091.
(21) Katz, H. E.; Huang, J. Ann. Rev. Mater. Res. 2009, 39, 71.
(22) Burghard, M.; Klauk, H.; Kern, K. Adv. Mater. 2009, 21, 2586.
(23) Mori, T. J. Phys.-Condes. Matter 2008, 20.
(24) Roncali, J.; Leriche, P.; Cravino, A. Adv. Mater. 2007, 19, 2045.
(25) Facchetti, A. Mater. Today 2007, 10, 28.
(26) Dodabalapur, A. Mater. Today 2006, 9, 24.
(27) Anthony, J. E. Chem. Rev. 2006, 106, 5028.
(28) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99.
(29) Tessler, N.; Preezant, Y.; Rappaport, N.; Roichman, Y. Adv. Mater. 2009, 21, 2741.
(30) Sirringhaus, H. Adv. Mater. 2009, 21, 3859.
(31) Braga, D.; Horowitz, G. Adv. Mater. 2009, 21, 1473.
(32) Shirota, Y.; Kageyama, H. Chem. Rev. 2007, 107, 953.
(33) Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296.
(34) Coropceanu, V.; Cornil, J.; da Silva, D. A.; Olivier, Y.; Silbey, R.; Bredas, J. L. Chem. Rev. 2007, 107, 926.
(35) Wurthner, F.; Schmidt, R. ChemPhysChem 2006, 7, 793.
(36) Kitamura, M.; Arakawa, Y. J. Phys.-Condes. Matter 2008, 20.
(37) Murphy, A. R.; Frechet, J. M. J. Chem. Rev. 2007, 107, 1066.
(38) Hotta, S.; Waragai, K. Adv. Mater. 1993, 5, 896.
(39) Videlot, C.; Ackermann, J.; Blanchard, P.; Raimundo, J. M.; Frere, P.; Allain, M.; de Bettignies, R.; Levillain, E.; Roncali, J. Adv. Mater. 2003, 15, 306.
(40) Romanazzi, G.; Marinelli, F.; Mastrorilli, P.; Torsi, L.; Sibaouih, A.; Raisanen, M.; Repo, T.; Cosma, P.; Suranna, G. P.; Nobile, C. F. Tetrahedron 2009, 65, 9833.
(41) Pouchain, L.; Aleveque, O.; Nicolas, Y.; Oger, A.; Le Regent, C. H.; Allain, M.; Blanchard, P.; Roncali, J. J. Org. Chem. 2009, 74, 1054.
(42) Gao, J. H.; Li, L. Q.; Meng, Q.; Li, R. J.; Jiang, H.; Li, H. X.; Hu, W. P. J. Mater. Chem. 2007, 17, 1421.
(43) Takimiya, K.; Kunugi, Y.; Toyoshima, Y.; Otsubo, T. J. Am. Chem. Soc. 2005, 127, 3605.
(44) Meng, H.; Sun, F. P.; Goldfinger, M. B.; Jaycox, G. D.; Li, Z. G.; Marshall, W. J.; Blackman, G. S. J. Am. Chem. Soc. 2005, 127, 2406.
(45) Newman, C. R.; Frisbie, C. D.; da Silva, D. A.; Bredas, J. L.; Ewbank, P. C.; Mann, K. R. Chem. Mat. 2004, 16, 4436.
(46) Frere, P.; Raimundo, J. M.; Blanchard, P.; Delaunay, J.; Richomme, P.; Sauvajol, J. L.; Orduna, J.; Garin, J.; Roncali, J. J. Org. Chem. 2003, 68, 7254.
(47) Videlot-Ackermann, C.; Ackermann, J.; Brisset, H.; Kawamura, K.; Yoshimoto, N.; Raynal, P.; El Kassmi, A.; Fages, F. J. Am. Chem. Soc. 2005, 127, 16346.
(48) Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J.; Dodabalapur, A. Adv. Mater. 1997, 9, 36.
(49) Katz, H. E.; Bao, Z. N.; Gilat, S. L. Accounts Chem. Res. 2001, 34, 359.
(50) Locklin, J.; Li, D. W.; Mannsfeld, S. C. B.; Borkent, E. J.; Meng, H.; Advincula, R.; Bao, Z. Chem. Mat. 2005, 17, 3366.
(51) Chanteau, S. H.; Tour, J. M. J. Org. Chem. 2003, 68, 8750.
(52) Takimiya, K.; Konda, Y.; Ebata, H.; Niihara, N.; Otsubo, T. J. Org. Chem. 2005, 70, 10569.
(53) Janzen, D. E.; Burand, M. W.; Ewbank, P. C.; Pappenfus, T. M.; Higuchi, H.; da Silva, D. A.; Young, V. G.; Bredas, J. L.; Mann, K. R. J. Am. Chem. Soc. 2004, 126, 15295.
(54) Kashiki, T.; Shinamura, S.; Kohara, M.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H. Org. Lett. 2009, 11, 2473.
(55) Kromer, J.; Bauerle, P. Tetrahedron 2001, 57, 3785.
(56) Das, J. P.; Roy, S. J. Org. Chem. 2002, 67, 7861.
(57) Liu, Q.; Lan, Y.; Liu, J.; Li, G.; Wu, Y. D.; Lei, A. W. J. Am. Chem. Soc. 2009, 131, 10201.
(58) Wu, Y. T.; Tai, C. C.; Lin, W. C.; Baldridge, K. K. Org. Biomol. Chem. 2009, 7, 2748.
(59) Kung, Y.-H.; Chen, Y.-S.; Tai, C.-C.; Liu, W.-S.; Shin, C.-C.; Ma, C.-C.; Tsai, Y.-C.; Wu, T.-C.; Kuo, M.-Y.; W, Y.-T. Chem Eur. J. 2010, 16, 5909.
(60) 龔雲華 合成苯駢[1,2-k;4,5-k]二螢蒽衍生物; 國立成功大學碩士論文, 民國97年.
(61) Wu, Y. T.; Kuo, M. Y.; Chang, Y. T.; Shin, C. C.; Wu, T. C.; Tai, C. C.; Cheng, T. H.; Liu, W. S. Angew. Chem. Int. Edit. 2008, 47, 9891.
(62) 張猷定 多取代8,8a-雙氫環戊[a]茚的合成和光物理性質的探討; 國立成功大學碩士論文, 民國96年.
(63) Araki, K.; Endo, H.; Masuda, G.; Ogawa, T. Chem. Eur. J. 2004, 10, 3331.
(64) Honciuc, A.; Metzger, R. M.; Gong, A. J.; Spangler, C. W. J. Am. Chem. Soc. 2007, 129, 8310.
(65) Wu, R. L.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906.
(66) Dang, T. T. M.; Park, S. J.; Park, J. W.; Chung, D. S.; Park, C. E.; Kim, Y. H.; Kwon, S. K. J. Polym. Sci. Pol. Chem. 2007, 45, 5277.
(67) van Breemen, A.; Herwig, P. T.; Chlon, C. H. T.; Sweelssen, J.; Schoo, H. F. M.; Setayesh, S.; Hardeman, W. M.; Martin, C. A.; de Leeuw, D. M.; Valeton, J. J. P.; Bastiaansen, C. W. M.; Broer, D. J.; Popa-Merticaru, A. R.; Meskers, S. C. J. J. Am. Chem. Soc. 2006, 128, 2336.
(68) Wakioka, M.; Nagao, M.; Ozawa, F. Organometallics 2008, 27, 602.