臺灣博碩士論文加值系統

第一部份，利用鹼使香豆素和N-烷基喹啉碘鹽進行環化反應，並有效的合成出多個香豆素與啡啶稠合雜環化合物。合成之開環及其閉環具有可被鎖定之分子開關性質，意即閉環化合物除了可藉由pH值調控產生開環化合物，此外可由氧化與還原反應進一步鎖定為對pH值不敏感之形式。
第二部份，利用微波輔助一鍋合成假性多組成反應出以香豆素與4-甲基喹啉為主體之吡螺喃化合物並探討其分子開關性質。其除了具酸鹼致變色性質外，此二化合物亦對光敏感，在紫外光照射下會有明顯的顏色改變，且光誘導開環產物可藉由含有Imidazoline之磁性奈米粒子回復至起始物，並且可利用磁鐵輕易的使磁性奈米粒子與有機化合物分離。

In part one, a number of coumarin/phenanthridine-fused heterocycles were efficiently synthesized using base-mediated annulation of coumarin and N-alkylquinolinium iodide as a key step. The prepared compounds and their corresponding ring open forms exhibit lockable switching properties, that is, they are interchangeable via pH control and can also be further converted to their “pH-inert” forms by chemical oxidation and reduction.
In part two, two new pyranocoumarins were synthesized and characterized via one-pot, microwave-assisted pseudo multicomponent condensations of coumarin and 4-methylquinoline to investigate their molecular switching properties. In addition to exhibiting acidichromism, both compound were found to be light-sensitive and have a distinct change of color upon UV irradiation. The reaction can be reverted by treating the photogenerated products with imidazoline-functionalized magnetic nanoparticles, which can be swiftly recycled with an external permanent magnet.

摘要............................................................................................................................I
Abstract..................................................................................................................II
圖譜目錄............................................................................................................VII
圖表目錄..........................................................................................................VIII
第一章 緒論....................................................................................................1
1.1 香豆素簡介.......................................................................................1
1.2 分子開關.............................................................................................4
1.3 微波輔助有機合成反應.................................................................8
1.4 多組成反應......................................................................................11
1.5 奈米粒子簡介.................................................................................14
第二章 研究動機......................................................................................18
2.1 合成以香豆素與啡啶稠合雜環化合物作為潛在分子開
關........................................................................................................18
2.2 藉由微波輔助進行一鍋假性多組成反應合成哌喃香豆
素作為分子開關............................................................................21



第三章 結果與討論................................................................................24
3.1 合成以香豆素與啡啶稠合雜環化合物作為潛在分子開
關........................................................................................................24
3.2 藉由微波輔助進行一鍋假性多組成反應合成哌喃香豆
素作為分子開關............................................................................30
第四章 結論..................................................................................................52
第五章 實驗部份......................................................................................53
5.1 儀器設備及試藥來源...................................................................53
5.2 化合物的合成.................................................................................56
第六章 參考文獻......................................................................................63
第七章 光譜資料......................................................................................66

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