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研究生: 柳逸軒
Yi-Shiuan Liou
論文名稱: 多並苯醚類化合物的合成與多並苯醚類化合
The Synthesis of Acene Ethers and Sulfides and Application of Such Compounds in Constructing Self-Assembly Monolayer
指導教授: 侯敦仁
Duen-Ren Hou
林質修
Chih-Hsiu Lin
口試委員:
學位類別: 碩士
Master
系所名稱: 理學院 - 化學學系
Department of Chemistry
畢業學年度: 94
語文別: 中文
論文頁數: 238
中文關鍵詞: 多並苯化合物四並苯醚類交換反應
外文關鍵詞: ether exchange reaction, acene, anthracene, tetracene
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  • 摘要
    本篇論文目標為合成多並苯醚類化合物,並且利用這些化合物於自組裝分子單層薄膜的研究。除了沿用本實驗室之前開發的酸催化醚類交換反應外,並開發用於不同取代位置交換反應的新條件,更進一步將此策略延伸至四並苯化合物。經交換反應所得的蒽與四並苯硫醚30, 52等化合物可繼續進行retro-Micheal反應產生硫陰離子並進一步官能化。所得的硫酯化合物目前無法成功的用於自組裝分子薄膜建構,期待未來以硫腈或其他官能基吸附方式完成此一目標。


    Abstract
    The major goal of this thesis is to synthesize acene ethers and sulfides and employ these compounds for the construction of self assembly monolayer (SAM). Continuing our “acid catalyzed ether-ether and ether-sulfide exchange” protocol, we synthesized a range of substituted anthracene derivatives. We then extended this methodology to tetracenes derivatives. Compounds like 30, 52 thus obtained can undergo retro-Micheal reaction to generate thiolate anions in situ and further functionalized. A variety of anthracene and tetracene thioester derivatives were obtained with such strategy. However, we have not been successfully using these thioesters in SAMs construction at present. From other’s preliminary result, we expect thiocyanide to be another suitable option in such pursuit.

    章節目錄 英文摘要 ……………………………………………………………....I 中文摘要 ……………………………………………………………...II 謝誌……...……………………………………………………………...III 章節目錄 ……………………………………………………………..IV 圖表目錄 …………………………………………………………......VI 第一章 緒論 …......……………………………………………………1 1-1 前言 ...…………………………………………………………..1 1-2 多並苯 (polyacene) 化合物的重要性與應用 ………………..2 1-3 多並苯化合物合成方法的回顧……………………………..….4 1-4 自組裝單層分子薄膜 (self-assembled monolayers,SAMs)…..8 1-5 研究動機與目的 ....………………………………………..….11 第二章 結果與討論 ..………………………………………………..15 2-1 氧醚以及硫醚之多並苯化合物的合成策略………………….15 2-2 合成部份 ..…………………………………………………….17 2-2-1 氧醚蒽化合物的合成….…………………………..……..17 2-2-2 氧醚四並苯化合物的合成…………………………….....20 2-2-3 用於自組裝分子單層薄膜的蒽硫醚化合物的合成.........26 2-2-4 用於自組裝單層分子薄膜之醚類四並苯化合物的合成.35 2-2-5 醚類多並苯化合物之紫外可見光及螢光光譜的比較….41 2-3 自組裝分子薄膜的製備 ………………………………….….46 2-3-1 前言 ………………………………………………...……46 2-3-2 自組裝分子薄膜之製備步驟 ……………….…………..47 2-3-3 自組裝分子薄膜之吸附情形與紅外光譜數據 ……….. 49 2-3-4 對於自組裝分子薄膜未來的改進以及方向…………….55 2-4 結論 ………………………………………………………...…58 第三章 實驗部分 …………………………………………………....59 3-1 化合物結構之鑑定 …………………………………………...59 3-2 化合物之合成步驟 …………………………………...………60 3-3 金矽晶片的製備 …..……………………………………...…120 3-3-1 基材來源 ……………………………………………….120 3-3-2 蒸鍍金之儀器 ………………………………………….120 3-3-3 金片基材的製備 ………………………………..……...120 3-3-4 觀測自組裝分子薄膜用之儀器 ……………………….121 第四章 參考文獻 …………………………………………………122 附錄 …………………………………………………………………125 化合物之1H NMR 光譜、化合物之13C NMR 光譜

    第四章 參考文獻
    1. (a) Brenner, Alfred E. Science 1997, 275, 1401. (b) Lundstrom, Mark
    Science 2003, 299, 210.
    2. (a) Ratner M. Nature 2005, 435, 575. (b) Barker, P. A.; Street-Perrott, F. A.; Leng, M. J.; Greenwood, P. B.; Swain, D. L.; Perrott, R. A.; Telford, R. J.; Ficken, K. J. Science 2001, 292, 2303. (c) Tour, J. M.; Kozaki, M.; Seminario, J. M. J. Am. Chem. Soc. 1998, 120, 8486.
    3. (a) Tour, J. M. Acc. Chem. Res. 2000, 33, 791. (b) Reed, M. A.; Tour, J. M. Sci. Am. 2000, 282, 86. (c) Gimzewski, J. K.; Joachim, C. Science 1999, 283, 1683. (d) Goldhaber-Gordon, D.; Montemerlo, M. S.; Love, J. C.; Opiteck, G. J.; Ellenbogen, J. C. Proc. IEEE 1997, 85, 521.
    4. Kertesz, M.; Hoffmann, R. Solid State Comun. 1983, 47, 97.
    5. Kivelson, S.; Chapman, O. L. Phys. Rev. B 1983, 28, 7236.
    6. Houk, K. N.; Lee, P. S.; Nendel M. J. Org. Chem. 2001, 66, 5517.
    7. Pope, M.; Kallmann, H. P.; Magnante, P. J. Chem. Phys. 1963, 38, 2042.
    8. (a) Lin, Y. Y.; Gundlach, D. J.; Jackson, T. N.; Nelson, S. F.; Schlom, D. G. IEEE Electron Device Lett. 1997, 18, 87. (b) Mattheus, C. C.; Dros, A. B.; Baas, J.; Oostergetel, G. T.; Meetsma, A.; de Boer, J. L.; Palstra, T. T. M. Synth. Met. 2003, 138, 475.
    9. (a) Campbell R. B.; Robertson J. Monteath.; Trotter J. Acta Cryst. 1961, 14, 705. (b) Denis Fichou. J. Mater. Chem. 2000, 10, 571.
    10. (a) John E. Anthony.;Chris D.Sheraw.; Thomas N. Jackson.; Dave L. Eaton. Adv. Mater. 2003, 15, 2009. (b) Toshiyasu Suzuki.; Youichi Sakamoto.; Masafumi Kobayashi.; Yuan Gao.; Yasushi Fukai.; Youji Inoue.; Fumio Sato.; Shizuo Tokito. J. Am. Chem. Soc. 2004, 126, 8138.
    11. (a) Robert J. Hamers.; Ali Afzali.; Kevin P. Weidkamp.; Rudolf M. Tromp. J. Am. Chem. Soc. 2004, 126, 12740. (b) Ali Afzali.; Christos D. Dimitrakopoulos.; Tricia L. Breen. J. Am. Chem. Soc. 2002, 124, 8812.
    12. (a) Wong Henry N. C.; Chan Siu-Hin.; Yick Chung-Yan. Tetrahedron, 2002, 58, 9413. (b) Wong Henry N. C.; Yick Chung-Yan.; Chan Siu-Hin. Tetrahedron Letters, 2000, 41, 5957.
    13. Pozzo Jean-Luc.; Clavier Gilles M.; Colomes Michel.; Bouas-Laurent Henri. Tetrahedron, 1997, 53, 6377.
    14. Desvergne Jean-Pierre.; Hopf Henning.; Reichwagen Jens.; Guerzo Andre´ Del.; Belin Colette.; Bouas-Laurent Henri. Org. Lett, 2005, 7, 971.
    15. Colin Nuckolls.; Cherie R. Kagan.; George S. Tulevski.; Qian Miao.; Masafumi Fukuto.; Rebecca Abram.; Benjamin Ocko.; Ronald Pindak.; Michael L. Steigerwald. J. Am. Chem. Soc. 2004, 126, 15048.
    16. Lin Chih-Hsiu.; Radhakrishnan Krishnan. Chem. Commun, 2005, 504.
    17. Lin Chih-Hsiu.; Radhakrishnan Krishnan. Synlett, 2005, 14, 2179.
    18. Bigelow, W. C.; Pickett, D. L.; Zisman, W. A. J. Colloid Interface Sci. 1946, 1, 513.
    19. Nuzzo, R. G.; Allara, D. L. J. Am. Chem. Soc. 1983, 105, 4481.
    20. (a) Wells, M.; Crooks, R. M. J. Am. Chem. Soc. 1996, 118, 3988. (b) Sirkar, K.; Revzin, A.; Pishko, M. V. Anal. Chem. 2000, 72, 2930.
    21. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550.
    22. (a) Brockman, J. M.; Frutos, A. G.; Corn, R. M. J. Am. Chem. Soc. 1999, 121, 2629. (b) Dong, Y.; Shannon, C. Anal. Chem. 2000, 72, 2371.
    23. Tour, J. M.; Jones, L., II.; Pearson, D. L.; Lamba, J. S.; Burgin, T. P.; Whitesides, G. W.; Allara, D. L.; Parikh, A. N.; Atre S. J. Am. Chem. Soc. 1995, 117, 9529.
    24. Lu, Lingang.; Chen, Qiyin.; Zhu, Xiaozhang.; Chen, Chuanfeng.
    Synthesis 2003, 16, 2464.
    25. Roeland J. M. Nolte.; Bastienne B. Wentzel.; Maurice P. J. Donners.; Paul L. Alsters.;Martinus C. Feiters. Tetrahedron. 2000, 56, 7797.
    26. Fred Wudl.; Dmitrii F. Perepichka.; Michael Bendikov.; Hong Mebg. J. Am. Chem. Soc. 2003, 125, 10190.
    27. Jean-Pierre Desvergne.; Jens Reichwagen.; Henning Hopf.; Andr´e Del Guerzo.; Colette Belin.; Henri Bouas-Laurent. Org. Lett. 2005, 7, 971.
    28. Vincenzo Balzani.; Roberto Ballardini.; Wim Dehaen.; Adele E. Dell’Erba.; Franc¸isco M. Raymo.; J. Fraser Stoddart.; Margherita Venturi. Eur. J. Org. Chem. 2000, 591.
    29. Charles Mioskowski.; Jean-Michel Becht.; Alain Wagner. J. Org. Chem. 2003, 68, 5758.
    30. Paul Caluwe.; Nagaraj Shyamasundar. J. Org. Chem. 1981, 46, 811.
    31. Gregor Witte.; Daniel Ka¨ fer.; Piotr Cyganik.; Andreas Terfort.; Christof Wo¨. J. Am. Chem. Soc. 2006, 128, 1723.
    32. Marc D. Porter.; Thomas B. Bright.; David L. Allara.; Christopher E. D. Chidseyi. J. Am. Chem. Soc. 1987, 109, 3559
    33. Marye Anne Fox.; Jun Hu. J. Org. Chem. 1999, 64, 4959.
    34. Christopher E. D. Chidsey.; Ronald L. Cicero.; Matthew R. Linford. Langmuir. 2000, 16, 5688.
    35. Tour J. M.; Ciszek J. W. Chem. Mater. 2005, 17, 5684.

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