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標題: | 在一級胺化合物上引入氮異環碳烯官能基團之簡易方法 Introduction of NHC Moiety to Primary Amines Through Phthalimide Linkage |
作者: | Kai-En Peng 彭愷恩 |
指導教授: | 邱靜雯(Ching-Wen Chiu) |
關鍵字: | 氮異環碳烯,一級胺化合物, NHC,phthalimide linkage, |
出版年 : | 2016 |
學位: | 碩士 |
摘要: | 近年來,氮異環碳烯已被大量地研究,然而氮異環碳烯的合成仍存在一定困難性,特別是高對稱性的橋接型多牙氮異環碳烯,其合成之方式更需改善。為了克服在合成上的困難,我們設計了一個簡易的組裝合成法,將氮異環碳烯單元引入至各式各樣幾何構型的分子骨架中。在此研究中,我們利用一個帶有咪唑鹽與鄰苯二甲酸酐的雙官能型的積木分子,藉由一級胺基與鄰苯二甲酸反應形成的鄰苯二酰亞胺單元將多個氮異環碳烯的前驅物,咪唑鹽,串聯成一維、二維、三維等具有高對稱性骨架之多咪唑鹽化合物,之後在藉由乙基化來合成多牙氮異環碳烯的前驅物。此類氮異環碳烯可進一步與鎳金屬錯合物進行反應,得到各種幾何形狀的多牙氮異環碳烯之鎳金屬錯合物,並應用於末端炔類的氫硫化催化反應。除此之外,我們還將上述之組裝合成方法應用到胺基酸,形成帶有胺基酸分子的咪唑鹽與其相對應的氮異環碳烯前驅物,這些碳烯前去物將來可望合與金屬形成帶有胺基酸分子的有機金屬錯合物,並藉由引入生物分子的方式達到增加氮異環碳烯金屬錯合物的生物活性與選擇性,進一步達到降低投藥量之成效。 N-heterocyclic carbenes (NHCs) have been widely studied recent years. However, the synthesis of NHC could sometimes be complicated, especially when non-chelating symmetrical poly-functional carbene ligands are anticipated. Therefore, we decided to develop a simple method to introduce NHC unit to various molecular backbones using a sole NHC precursor. In this research, a LEGO brick bifunctional ligand, which bears an imidazole moiety on one side of the molecule and phthalic anhydride functionality on the other side, was synthesized. While the imidazole part represents the NHC precursor, the phthalic anhydride group reacts with primary amine containing molecule to introduce the NHC moiety via phthalimide linkage. With this synthetic protocol, poly NHCs and the corresponding poly-nuclear nickel complexes with 1-D, 2-D, and 3-D molecular structure were synthesized. Catalytic performances of these poly-Ni complexes illustrated the negligible interactions between the nickel centers. Furthermore, the synthetic protocol was found to be applicable to various amino acids to give the amino acid tethered benzimidazolium salts and the corresponding metal complexes. The combination of amino acid and NHC ligand is anticipated to improve the bio-compatibility of NHC-metal complexes for selective drug delivery. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/51072 |
DOI: | 10.6342/NTU201600298 |
全文授權: | 有償授權 |
顯示於系所單位: | 化學系 |
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