有機矽烷化合物（Organosilane）具有相當廣泛的應用性，在有機合成上可藉由檜山耦合反應（Hiyama coupling reaction）與鹵素化合物反應生成碳-碳鍵結；並且在許多生物活性之分子中也有矽烷官能基的存在；除此之外文獻也報導有機矽烷化合物在應用材料具有特別的性質。我們成功研發出以未活化的金屬鎂和活化子在一價銅的催化下藉由巴比艾爾型式（Barbier-type）反應可將芳香族溴化合物在一鍋型式（One-pot）的反應條件下合成有機矽烷化合物。

    另一個部份，我們合成設計化學感測分子，以7-羥基吩噁嗪酮（Resorufin）和星狀化合物為主架構，在外圍合成鉗合基（Binding-site），探討其在各種重金屬離子滴定上的紫外光吸收變化。

As we known, the applications of organoslianes and their derivatives are widely studied. In organic synthesis, the formation of a carbon-carbon bond can be achieved by Hiyama coupling reaction of organohalide with organosilane. We also can observe organosilanes behave as a structural moiety in many biologically active compounds. Furthermore, orgasilanes exhibit many unique properties which were observed in material compound.   Herewith, we report an efficient one-pot synthetic method by using unactivated magnesium, activator and copper(I) reagent that transform arylhilade into arylsilane under a Barbier-type reaction condition. 

    On the other part, we synthesize heavy metal sensing molecules based on Resorufin and star-shaped structures. We modify these molecules with a binding-site and measure their maximum UV-Vis absorption by titration of heavy-metal cations.

圖目錄（FIGURE）	IV
圖目錄（SCHEME）	V
表目錄	VII
第一章 緒論	1
1-1有機矽烷化合物的重要性	1
1-1-1在檜山耦合反應（Hiyama Coupling Reaction）上的應用	2
1-1-2 在材料上的各種應用	8
1-1-3 在生物活性分子上的應用	15
1-2 有機矽烷化合物的合成方法	19
1-2-1 有機金屬試劑親和取代反應	20
1-2-2過渡金屬催化的耦合反應	22
1-2-3 有機金屬試劑的耦合反應	27
1-3巴比艾爾反應介紹	30
1-3-1 金屬活化巴比艾爾型式	30
1-3-2 巴比艾爾型式反應在合成上的應用	35
第二章 結果與討論	42
2-1 反應條件的測試	42
2-2 有機矽烷化合物的合成	49
2-3 結論	52
第三章 緒論-第二部份	53
3-1重金屬污染的危害	54
3-2 化學感測分子的原理與介紹	60
第四章 結果與討論-第二部份	63
4-1 以 7-羥基吩噁嗪酮（RESORUFIN）為主架構的子合成探討	63
4-2 星狀分子為主架構的分子合成探討	67
4-3 發光性質與重金屬離子滴定測試	71
4-4 結論	86
第五章 實驗與儀器步驟	87
5-1 實驗步驟	87
5-2 溶劑乾燥	93
參考資料	96

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