臺灣博碩士論文加值系統

吡唑類為一五員環之芳香雜環化合物，其被視為一種生物鹼，在藥物之應用上具有退燒、止痛、抗發炎、鎮靜、鬆弛肌肉及抗菌等功能，其於製藥工業上占有高度之重要性；另外，其雜環與共振之特徵，亦被應用於有機發光二極體(organic light-emitting diode，OLED)材料之結構上。由此可知，在工業及學術研究上，吡唑類化合物具有相當之廣度。
在藥物之應用上，近年常有研究報告指出特定之吡唑衍生物可有效且選擇性地抑制A3腺苷受體(A3 adenosine receptor，A3AR)，達到抗氣喘、抗發炎、調節細胞生長及保護腦部等作用，使得此類吡唑衍生物日益重要。
在有機發光二極體材料之應用上，由於吡唑環上之氮原子及雙鍵組成具特別之電子性，因此，吡唑環亦可被導入光電材料之結構中，擔任傳遞電子之角色。
鑒於上述各類吡唑衍生物之廣泛用途，本論文主要以雪梨酮(sydnone)為起始物進行1,3-雙極環化加成反應(1,3-dipolar cycloaddition reaction)得吡唑雜環
，再利用各種不同官能基之導入，合成一系列吡唑衍生物；以不同之功能性區分，可將本系列吡唑衍生物歸類為A3腺苷受體拮抗劑(A3 adenosine receptor antagonists)與小分子發光材料(small molecular electroluminescence materials)兩種，論文內容針對本系列吡唑化合物之合成方法、基本性質及應用測試等進行研究及探討。

Pyrazole is the aromatic heterocyclic compound with the five-membered ring, and it is usually considered a kind of alkaloid. Derivatives of pyrazole are important compounds in pharmaceutical industry, and they are used for their antipyretic, anti-inflammatory, antipyretic, tranquilizing, muscle relaxing and antibacterial activities. In addition, they are also applied in organic light-emitting diode(OLED).
The potential therapeutical applications of antagonizing the A3 adenosine receptor(A3 AR) by derivatives of pyrazole have been investigated in recent year. The derivatives of arylpyrazoloquinolinone are A3 AR antagonists. This kind of antagonist with highly selectivity is being sought as antiasthmatic, anti-inflammatory and cerebroprotective agents.
In recent years, the electroluminescence materials with blue light-emitting have attracted great attention. As well known, pyrazole is a kind of blue light-emitting material. It is suitable to be applied in OLED after introduce fluorescent group in the pyrazole core.
In this investigation, a series of arylpyrazoloquinolinones were synthesized rapidly via 1,3-dipolar cycloaddition and Suzuki coupling. Compare with previous references, we used cheaper reagents and convenience method. In addition, a new category of small molecular electroluminescence materials was synthesized by the synthetic routes we designed. The properties of optics, electrochemistry and thermology were performed by UV, PL, CV and DSC. The EL devices of materials were also performed by vacuum deposition and brightness meter.

第一章、前言……………………………………………………………1
一、雪梨酮化合物之簡介……………………………………………1
二、腺苷之簡介………………………………………………………6
三、有機發光二極體之簡介…………………………………………13
第二章、腺苷受體拮抗劑之合成………………………………………27
一、初期設計之合成路徑…………………………………………27
二、以二步驟方法合成喹啉酮衍生物………………………………29
三、以一鍋化(one-pot)法合成喹啉酮衍生物………………………33
四、實驗步驟…………………………………………………………35
第三章、含噻吩-吡唑雜環發光材料之合成..................49
一、合成之設計.......................................49
二、實驗部分.........................................55
三、基本性質測試......................................63
第四章、含1,3,4-二唑發光材料之合成…………………………..….81
一、合成之設計………………………………………………………81
二、實驗部分..........................................85
三、基本性質測試......................................94
第五章、有機發光元件之組裝................................105
第六章、結論............................................108
參考文獻...............................................110

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