本論文主要合成N型OFET材料，以一系列具拉電子基苝與蒽衍生物探討其合成、光電性質與OFET電性測試。由於接上benzimidazole的蒽與苝溶解度過差，我們在其中幾個化合物接上碳鏈來增加溶解度，合成結構如下圖。
我們以DFT以及半經驗法則計算方法來計算其電子雲分布狀況；以循環伏特安培法（CV）來測量氧化還原電位，以便進一步地計算出HOMO與LUMO能階電位；藉由紫外-可見光吸收光譜儀和螢光儀來觀察其光學性質；使用熱重分析儀（TGA）來推測其熱穩定性。其中QA-1有晶體的養成，經過X-ray的分析了解其堆疊特性。最後以Au或Ca/Al合金為電極做電性測試。

In the thesis we designed two series of n-type electron transport organic semiconducting materials. A detailed studies on their synthesis, optical, electrochemical properties and field-effect mobility has been carried out.We have successfully synthesized a series of perylene bisimide and anthracene derivatives with substitution of electron-withdrawing groups. When benzimidazole attach to anthracene and perylene, it renders the materials become very insoluble in most organic solvent. To improve the solubility, we introduced long carbon chain into the framework of the benzimidazole group. The structures of the materials are shown in the bottom.
We employed DFT and semi-empirical methods to compute the molecular orbitals of the compounds. The HOMO and LUMO energy levels were experimentlly derived from cyclic voltametry (CV) data. The optical properties of absorption and emission were explored by UV-Visible and fluorescence spectroscopic methods. The heat stability were determined by TGA (thermogravinetric analyzer). Some of them are further characterized by single crystal X-ray analysis.

參考資料
[1]Pope, M.; Kallmann, H. P.; Magnante, P. J. Chem. Phys. 1963, 38, 2024.
[2]Chiang, C. K.; Fincher, C. R.; Park, Y. W.; Heeger, A. J. Phys. Rev. Lett. 1977, 39, 1098.
[3]Tsumura, A.; Koezuka, H.; Ando, T. Appl. Phys. Lett. 1986, 49, 1210
[4]Newman, C. R.; Frisbie, C. D.; da Silva Filho, D. A.; Bre´das, J.-L.; Ewbank, P. C.; Mann, K. R. Chem. Mater. 2004, 16, 4436.
[5]Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296.
[6]孫允武, 中興大學物理系應用電子學線上講義.
[7]Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Katz, H. E.; Marks, T. J. Angew. Chem., Int. Ed. 2003, 42, 3900.
[8]Molinari, A. S.; Alves, H.; Facchetti, A.; Morpurgo, A. F. J. Am. Chem. Soc. 2009, 131, 2462.
[9]Chua, L.-L.; Zaumseil1, J.; Chang, J.-F.; Ou, E. C.-W.; Ho, P. K.-H.; Sirringhaus, H.; Friend, R. H. Nature. 2005, 434, 194.
[10]Singh, T. B.; Meghdadi, F.; Günes, S., Marjanovic, N.; Horowitz, G.; Lang, P.; Bauer, S.; Sariciftci, N. S. Adv. Mater. 2005, 17, 2315.
[11]Dutreilh-Colas, M.; Yan, M.; Labrot, P.; Delorme, N.; Gibaud, A. ; Bardeau, J.-F. Surface Science. 2008, 602, 829.
[12]Menard, E.; Podzorov, V.; Hur, S.-H.; Gaur, A.; Gershenson, M. E.; Rogers, J. A. Adv. Mater. 2004, 16, 2097.
[13]Horiuchi, K.; Nakada, K.; Uchino, S.; Hashii, S.; Hashimoto, A.; Aoki, N.; Ochiaib, Y. Appl. Phys. Lett. 2002, 81, 1911.
[14]Bao, Z.; Lovinger, A. J.; Brown, J. J. Am. Chem. Soc. 1998, 120, 207.
[15]Facchetti, A.; Mushrush, M.; Kalz, H. E.; Marks, T. J. Adv. Mater. 2003, 15, 33.
[16]Würthner, F.; Chem. Commun. 2004, 1564.
[17]Horowitz, G.; Kouki, F.; Spearman, P.; Fichou, D.; Nogues, C.; Pan, X.; Garnier, F. Adv. Mater. 1996, 8, 242.
[18]Tatemichi, S.; Ichikawa, M.; Koyama, T.; Taniguchi, Y. Appl. Phys. Lett. 2006, 89, 112108.
[19]Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 15259.
[20]Jones, B. A.; Ahrens, M. J.; Yoon, M.-H.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem., Int. Ed. 2004, 43, 6363.
[21]Li, Y.; Tan, L.; Wang, Z.; Qian, H.; Shi, Y.; Hu, W. Org. Lett. 2008, 10, 529.
[22]Lee, J. Y.; Chu, S. W.; Kim, J. S.; Park, Y. W. Appl. Phys. Lett. 2004, 84, 5383.
[23]Kaur, I.; Jia, W.; Kopreski, R. P.; Selvarasah, S.; Dokmeci, M. R.; Pramanik, C.; McGruer, N. E.; Miller, G. P. J. Am. Chem. Soc. 2008, 130, 16274.
[24]Meng, H.; Sun, F.; Goldfinger, M. B.; Jaycox, G. D.; Li, Z.; Marshall, W. J.; Blackman, G. S. J. Am. Chem. Soc. 2005, 127, 2406.
[25]Ito, K.; Suzuki, T.; Sakamoto, Y.; Kubota, D.; Inoue, Y.; Sato, F.; Tokito, S. Angew. Chem., Int. Ed. 2003, 42, 1159.
[26]Tannaci, J. F.; Noji, M.; McBee, J. L.; Tilley, T. D. J. Org. Chem. 2008, 73, 7895.
[27]Sakamoto, Y.; Suzuki, T.; Kobayashi, M.; Gao, Y.; Fukai, Y.; Inoue, Y.; Sato, F.; Tokito, S. J. Am. Chem. Soc. 2004, 126, 8138.
[28]Park, J.-H.; Chung, D. S.; Park, J.-W.; Ahn, T.; Kong, H.; Jung, Y. K.; Lee, J.; Yi, M. H.; Park, C. E.; Kwon, S.-K.; Shim, H.-K. Org. Lett. 2007, 9, 2573.
[29]Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Samson A.; Jenekhe, S. A. Chem. Mater. 2004, 16, 4556.
[30]Du, H.; Fuh, R. A.; Li, J.; Corkan, A.; Lindsey, J. S. Photochem. and Photobio. 1998, 68, 141.
[31]Youngblood, W. J. J. Org. Chem. 2006, 71, 3345.
[32]Dang, H; Levitus, M.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2002, 124, 136.
[33]Singh, A.; Sharp, A. P. J. Am. Chem. Soc. 2006, 128, 5998.
[34]Negishi, E.-I.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
[35]Chinchilla, R.; Na´jera, C. Chem. Rev. 2007, 107, 874.
[36]Tannaci, J. F.; Noji, M.; McBee, J.; Tilley, T. D. J. Org. Chem. 2007, 72, 5567.
[37]Tannaci, J. F.; Noji, M.; McBee, J. L.; Tilley, T. D. J. Org. Chem. 2008, 73, 7895.
[38]Würthner, F.; Osswald, P.; Schmidt, R.; Kaiser, T. E.; Mansikkama1ki, H.; Ko1nemann, M. Org. Lett. 2006, 8, 3765.
[39]Chen, Z.; Debije, M. G.; Debaerdemaeker, T.; Osswald, P.; Würthner, F. ChemPhysChem. 2004, 5, 137.
[40]Feng, J.; Liang, B.; Wang, D.; Xue, L.; Li, X. Org. Lett. 2008, 10, 4437.
[41]Goretzki, G.; Davies, S.; Argent, S. P.; Alsindi, W. Z.; Blake, A. J.; Warren, J. E.; McMaster, J.; Champness, N. R. J. Org. Chem. 2008, 73, 8808.
[42]Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem. Eur. J. 2001, 7, 2245.
[43]de Leeuw, D. M.; Simenon, M. M. J.; Brown, A. R.; Einerhand, R. E. F. Synth. Met. 1997, 87, 53.