合成醯肼-腙螢光分子及其葡萄糖感測研究

Synthesis of Hydrazine-Hydrazone Fluorescent Molecules and Their Glucose Sensing Research

張歆悅(HSIN YUEH CHANG)

指導教授 ： 葉美鈺

中原大學/理學院/化學系/碩士(2022年)

https://doi.org/10.6840/cycu202201267

摘要

Hydrazine-Hydrazone 醯肼-腙螢光有機分子具有高選擇性、靈敏度和普遍適用性，為新一代的螢光探針，可作為螢光傳感器和藥物載體的材料。
本次研究首先設計了醯肼-腙結合三種不同位向(鄰、間和對)硼酸的芘衍生物螢光分子3a、3b及3c。探討其發光特性，並透過三種不同的醣類(果糖、蔗糖和葡萄糖)進行光物理性質研究。然而發現了設計的醯肼-腙分子衍生物對於葡萄糖有非常高的選擇性，透過螢光光譜看見在450nm生成了很大的吸收波長。最後我們進一步探討葡萄糖對於分子的結合性質及其應用性。此為目前為止第一位將醯肼-腙分子應用至血糖螢光檢測的研究。
另外還設計了一款基於醯肼-腙結合三種不同位向(鄰、間和對)硼酸的咪唑-吲哚衍生物9a、9b及9c。在探討其發光特性的過程中，還發現了該衍生物獨特的光切換性質。並且利用此性質結合二維碼QR-code的設計應用至安全防偽工具隱形墨水當中。除此之外在葡萄糖添加的測試中，也可以看見螢光的轉變，因此成功發掘研究分子應用至血糖螢光感測的潛在應用性。在此是第一位將咪唑-吲哚衍生物做到具有雙效功能的研究，也是首次將該衍生物應用至隱形墨水及醣類感測中。
本篇研究發現利用醯肼-腙分子衍生物所設計出的螢光分子，在研究過程中發掘出許多應用價值性，在未來除了可以因應現今糖尿病監控血糖所需，成為新型的體外葡萄糖傳感器，提供快速且便利監控血糖的平台，改善舊型血糖儀體內檢測葡萄糖的缺點及感染風險，為世界上因糖尿病所困的人們提升生活品質。也可以作為隱形墨水，替有資料安全防護及防偽需求的人們提供一款新型工具，相信能成為防偽市場中極具價值的材料之一，應用價值指日可待。

關鍵字

硼酸 ； 芘衍生物 ； 螢光 ； 葡萄糖偵測 ； 咪唑??衍生物

並列摘要

Hydrazine-Hydrazone hydrazine-hydrazone molecules have high selectivity and universal applicability. Mainly become a new generation of fluorescent probes that can be used as materials for fluorescent sensors and drug carriers.
In the first part of this study, we designed and synthesized hydrazine-hydrazone-based pyrene derivatives 3a, 3b and 3c with three different orientations of boronic acids (ortho, meta and para). We systematically study the absorption and emission properties of 3a, 3b and 3c (with and without sugars). It was found that 3c has high selectivity for glucose molecules, accompanied by the pyrene excimer increasing (fluorescence spectrum at 450 nm). In the second part, we designed hydrazine-hydrazone-based imidazole-indole derivatives 9a, 9b and 9c. In exploring their luminescent properties, the photo-switching properties of these derivatives were also discovered. And this property is combined with the design and application of QR-code to create invisible ink for security and anti-counterfeiting tools. Additionally, the fluorescence sensing of blood glucose was also successfully explored.
This study found that the fluorescent molecules designed using hydrazine-hydrazone molecular derivatives have established many application values in the research process. In addition to meeting the needs of current diabetes monitoring blood sugar, it will become a new type of in vitro glucose sensor. Provide a platform for fast and convenient blood glucose monitoring, improve the shortcomings of old blood glucose meters in detecting glucose in vivo and the risk of infection, and improve the quality of life for people struck by diabetes. It can also be used as invisible ink to provide a new tool for people with data security protection and anti-counterfeiting needs. We believe it can become one of the most valuable materials in the anti-counterfeiting market, and its application value is just around the corner.

並列關鍵字

boronic acid ； pyrene ； fluorescent ； glucose sensor ； imidazole indole

參考文獻

第五章 參考文獻

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