合成高螢光效率的1, 8-萘醯亞胺衍生物

Synthesis of Highly Efficiency Fluorescent 1,8-Naphthalimide Derivatives

劉任偉(Jen-Wei Liu)

指導教授 ： 施增廉

淡江大學/理學院/化學學系碩士班/碩士(2014年)

https://doi.org/10.6846/TKU.2014.01264

摘要

1, 8-萘醯亞胺類衍生物的合成被廣泛的應用及探討，因為此類化合物都具有強烈螢光的特點。研究發現，該類化合物結構上萘環的平面性及穩定共軛系統產生良好的光化學穩定性、較大的斯托克斯位移及多重螢光的性質，因此該類化合物可作為螢光偵測器、抗腫瘤藥物、螢光分子顯影劑和螢光染料，近年來，許多科學家致力研究新穎的合成方式來合成1, 8-萘醯亞胺類衍生物，因此我們也設計了兩系列的衍生物，期望未來能近一步研究其應用。
第一類萘醯亞胺含氮衍生物：利用含氮化合物直接芳基化合成出所需化合物，其可作為金屬離子探針，利用金屬離子與孤對電子共價鍵產生螯合結構，改變螢光性質，或者進行構型-活性關係測試，作為抗腫瘤藥物。
第二類萘醯亞胺延伸平面性衍生物：利用鈀-銅金屬共同催化下與雜環直接進行碳-氫芳基化，從原本共振性較弱的藍紫色螢光改變為具有強共軛系統性質的黃綠色螢光，相信其未來能做為新穎的螢光標示劑或螢光染料。
這些經過不同官能基修飾的萘醯亞胺類衍生物只需要極低濃度即可產生強烈螢光性質，相信將來在各方面都會更被廣泛的使用。

關鍵字

1,8-萘醯亞胺 ； 螢光探針 ； 抗腫瘤藥物 ； 螢光分子顯影劑 ； 螢光染料

並列摘要

1, 8 - Naphthalimides derivatives have strong fluorescence characters and their synthesis have been widely studied. They have been commonly used as fluorescent probes, anticancer agents, fluorescent cellular imaging agents and fluorescent dyes. They possess planar scaffold and stable conjugated system to lead to more photochemical stability, large Stokes shift and multiple fluorescence properties.
Because 1, 8 - Naphthalimides derivatives have various application, therefore we want to explane a facile synthesis of derivatives to expect higher fluorescence efficiency.
The first part is synthesis of nitrogen 1, 8 - Naphthalimides derivatives. These compounds can be complex with metal ion through lone pairs to lead to chelating structure. The fluorescence properties would be changed that can be used the metal ion probe in the future. Furthermore we can test its structure – activity relationship (SAR) studies as anticancer agents.
The second part is synthesis of extended 1, 8 - Naphthalimides planarity derivatives. Arylation of azoles is mediated by Pd – Cu system. We can change the resulting adducts from weaker blue - violet fluorescence to stronger conjugated system with yellow-green fluorescence. It can be novel fluorescent labeling agents or fluorescent dyes.
Low concentrations, these different functional 1, 8 - Naphthalimides derivative to produce intense fluorescence properties. They can be more widely used in various aspects.

並列關鍵字

1,8-Naphthalimide Fluorescent probes ； Anticancer agents ； Fluorescent cellular imaging agents ； Fluorescent dyes

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