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研究生:陳佑昇
研究生(外文):You-Sheng Chen
論文名稱:合成以triketone為主體之潛在溶劑致變色試劑及設計以香豆素為主體之雙環化合物作為潛在之光致變色材料及分子開關
論文名稱(外文):Synthesis of novel triketone-based derivatives as potential solvatochromic colorantsandDesign and Sythesis of coumarin-base oxazobicycles as potential photochromic colorants and molecular switches
指導教授:楊定亞
指導教授(外文):Ding-Yah Yang
學位類別:碩士
校院名稱:東海大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2006
畢業學年度:94
語文別:中文
論文頁數:180
中文關鍵詞:溶劑致變色試劑光致變色材料分子開關
外文關鍵詞:solvatochromic colorantsphotochromic colorantsmolecular switches
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第一部份、合成以triketone為主體之潛在溶劑致變色試劑


  2-醯基-1,3環己雙酮衍生物在有機跟水溶劑下的主要構型已經鑑定。它的溶劑敏感性質被應用在設計極性敏感的螢光探針上。我們提出了以3-acetyl-7-(dimethylamino) -4-hydroxy-2H-chromen -2-one為主體設計一系列衍生物作為潛在的溶劑致變色試劑。合成出來的化合物4、7溶在非極性溶劑中(如二氯甲烷),主要是以endocyclic enol
形式存在,而且因為N,N-dimethylamino官能基的存在所以有很強的螢光。而化合物4、7溶在極性溶劑中(如甲醇),則沒有偵測到螢光,主要是以exocyclic enol形式存在。化合物4溶在非極性、極性溶劑中顏色都是無色,而化合物7溶在非極性溶劑中是橘色,而溶在極性中則為深紅色。

第二部份、設計以香豆素為主體之雙環化合物作為潛在之光致變色材料及分子開關


很多以香豆素為主體的oxazobicyclic化合物已經成功的合成出來,並且做為潛在的光化學變色試劑。在已經成功合成出的分子中,只有在苯環的鄰位位置有硝基的oxazobicycle才有光致變色物的性質,它包含了heterobicyclic骨架上的碳-氧鍵斷裂。照完光的產物結構已經說明是開環的亞胺,它是可逆的藉由加熱形成閉環的結構。
Part I、Synthesis of novel triketone-based derivatives as potential solvatochromic colorants.


The major tautomer of several triketone derivatives in organic and aqueous solutions has been determined. Their solvent-sensitive properties have been applied in design of a polarity-sensitive fluorescent probe.We propose the synthesis of Novel 3-acetyl-7-(dimethylamino) -4-hydroxy -2H-chromen-2-one-based derivatives as potential solvatochromic colorants. The synthesized compounds 4 and 7 exists mainly in the endocyclic enol form in non-polar solvents like methylene chloride and are highly fluorescent due to the presence of a N,N-dimethylamino group. Essentially no fluorescence was detected when compounds 4 and 7 was dissolved in polar solvents like methanol, where they exist mainly in the exocyclic enol form. Compound 4 in both non-polar and polar solvents is both colorless; compound 7 in non-polar solvents is orange, but in polar solvents is deep red.

Part II:Design and Sythesis of coumarin-base oxazobicycles as potential photochromic colorants and molecular switches



Several novel coumarin-based oxazobicyclic compounds have been synthesized and evaluated as potential photochromic colorants. Among the prepared molecules, only the oxazobicycle with a nitro substituent at ortho position of bridgehead benzene ring exhibits the expected photochromic behavior, which involved a C-O bond rupture of the heterobicyclic skeleton. The structure of the photo irradiation product has been elucidated to be the ring opened imine, which can be reverted to the original ring closed form upon heating.
目錄

誌謝……………………………………………………………I
第一部份中文摘要……………………………………............II
第二部份中文摘要……………………………………...........III
第一部份英文摘要……………………………….…….….... IV
第二部份英文摘要………………………..……….……....…V
目錄………………………………………..……….…….…VIII
圖譜目錄……………………………………………….…... XII
圖表目錄…………………………………………………... XIII

第一部份、合成以triketone為主體之潛在溶劑致變色試劑

壹、緒論……………………………………………………………….2
貳、研究動機………………………………………………………….5
參、結果與討論……………………………………………………….8
肆、結論……………………………………………………………….20
伍、實驗部份
一、儀器設備及試藥來源…………………………………….21
二、吸收光譜、螢光放射光譜測量及螢光量子產率的計算.22
三、化合物的合成…………………………………………….24
陸、參考資料………………………………………………………….27
柒、光譜資料………………………………………………………….28













第二部份、設計以香豆素為主體之雙環化合物作為潛在之光致變色材料及分子開關
壹、緒論……………………………………………………………….50
貳、結果與討論……………………………………………………….61
參、結論……………………………………………………………….81
肆、實驗
一、儀器設備及試藥來源……………………………………82
二、化合物的合成……………………………………………84
伍、參考資料…………………………………………………………99
柒、光譜資料………………………………………………………...101
第一部份、合成以triketone為主體之潛在溶劑致變色試劑
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2. Bamfield, P. “Phenomena Involving a Reversible Colour Change” in Chromic Phenomena. Ch. 1, 2002, 1-32.
3. Yokoyama, Y. Chem. Rev. 2000, 100, 1717-1740.
4. Boxer, S. G.; Bublitz, G. U. J. Am. Chem. Soc. 1998, 120, 3988-3992.
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Senchenya, I. N. Russian J. Gen. Chem. 2000, 70, 793-797.
6. Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaı¨lo, P. J. Org.
Chem.2001, 66, 256-261.
7. Knierzinger, A.; Wolfbeis, Otto S. J. Heterocycl. Chem. 1980, 17,
225-229.
第二部份、設計以香豆素為主體之雙環化合物作為潛在之光致變色材料及分子開關
1. Bouas-Laurent, H.; Dürr, H. “Organic Photochromism”, Pure Appl.
Chem. 2001, 73, 639-665.
2. Bamfield, P. “Phenomena Involving a Reversible Colour Change” in
Chromic Phenomena. Ch. 1, 2002, 1-32.
3. Fischer, E.; Hirshberg, Y. J. Chem. Soc. 1952, 4522.
4. Raymo, F. M. ; Sortino, S. ; Tomasulo, M. Org. Lett. 2005, 7, 1109-1112.
5. 林靜燦,碩士論文,東海大學應用化學所, 2005
6. Berkovic, G.; Krongauz; Weiss, V. Chem. Rev. 2000, 100, 1741-1754.
7. Matsuda, K.; Irie, M. J. Am. Chem. Soc. 2000, 122, 7195-7201.
8. Yokoyama, Y. Chem. Rev. 2000, 100, 1717-1740.
9. Irie, M. (Guest Editor) Chem. Rev. 2000, 100, 1683-1684.
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11. Wilner, I. Acc. Chem. Res. 1997, 30, 347-356.
12. Kawata, S.; Kawata, Y. Chem. Rev. 2000, 100, 1777-1788.
13. Parthenopoulos, D. A.; Rentzepis, P. M. Science 1989, 245, 843-845.
14. Kharlanov, V. A. J. Photochem and Photobiol A:Chemistry 1999,
122, 191-197.
15. Peters, A.; Vitols, C.; McDonald, R.; Branda, N. R. Organic Lett.
2003, 5, 1183-1186.
16. Chen, Y.; Zeng, D. X.; Fan, M. G. Organic Lett. 2003, 5, 1435-1437.
17. Peters, A.; and Branda, N. R. J. Am. Chem. Soc. 2003, 125, 3404
-3405.
18. Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O.
Tetrahedron 1997, 53, 9715-9726.
19. Tamaoki, N.; Keuren, E. V.; Matsuda, H. Appl. Phys. Lett. 1996,
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21. 王忍妃, 碩士論文, 東海大學應用化學所, 2005
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