有機螢光材料由於其有多元的應用，而受到了許多的關注，包含生物體內螢光成像、光動力療法、有機發光二極體、有機雷射材料等等。近年來，我們實驗室致力於開發雙態螢光材料及具放大自發輻射效應之有機雷射材料。本論文主要專注在開發新型螢光分子的雙態發射性質以及放大自發輻射性質，以評估其在雙態螢光材料及有機雷射材料的應用潛力。雙態螢光發射是指分子在固態和溶液態中皆能放出螢光，藉由測定其在固態以及溶液態的螢光量子產率，可以做不同層面上的應用，而放大自發輻射則是指螢光分子自發輻射增強的過程，可作為我們日後設計有機雷射材料的參考。 在本研究中，我們合成出多個螢光分子，以及量產本實驗室已畢業成員-李盈萱所合成的四取代乙烯系列模型分子，並量測與探討它們的光物理性質。這些模型分子結構的特性以及實驗觀察結果簡述如下: (1) 第一系列模型分子以苯並三唑接上含有嗎啉(Morpholine)的烷鏈為核心，具有標定細胞溶酶體之應用潛力。 (2) 第二系列模型分子以苯並三唑接上不同長度烷鏈為核心，接上噻吩結構單元，並以此結構作為基礎，向外接上不同推電子基團。 從非線性光學測定結果來看，我們發現延長分子共軛結構或於外圍加入推電子性官能基可以有效提升分子的雙光子激發截面值。 (3) 第三系列模型分子為四取代乙烯系列，經由光學量測發現和第二系列模型分子5、6皆具有放大自發輻射效應。;Organic fluorescent materials have attracted a lot of attention due to their diverse applications, including fluorescence imaging, photodynamic therapy, organic light-emitting diodes, organic laser materials, etc. For the recent years, we have dedicated to the development of dual-state fluo-rescent materials and organic laser materials. This thesis mainly discusses the dual-state emission properties and amplified spontaneous emission properties of our recently developed fluorescent molecules to evaluate their potential applications in dual-state fluorescent emission and organic lasers. Dual-state fluorescence emission means that a molecule can emit fluorescence in both the solid state and the solution state and such materials can be applied to different aspects. Amplified spontaneous emission refers to the process of enhanced spontaneous emission of fluorescent molecules and organic structures exhibiting such a feature can be used as a reference model for the design of organic laser materials in the future. In this research, we have synthesized several new fluorescent molecules, and re-produced a series of tetra-substituted ethylene model molecules which had been synthesized by Ms. Ying-Hsuan Lee, a former graduate of our laboratory. We explored their photophysical properties through corresponding measurements. These model molecules’ structural properties and our experimental observations can be briefly described as follows:
(1) The structures of model molecules of the first series possess benzotriazole units in the center, which are attached with morpholine unit and these compounds are designed to be applied to mark cellular lysosomes.
(2) The model molecules of the second series are derived from functionalized benzotriazole, thiophene, and various fluorenyl donoros units. From the results of nonlinear optical property measurements, we found that extending the molecular π-conjugated structure or introducing electron-pushing functional groups can effectively improve the overall molecular two-photon excitation cross section values.
(3) The model molecules of the third series are based on the scaffold of tetra-substituted ethylene. Through corresponding optical measurements, it was found that model molecules 5 and 6 of the second series and all the members of the third series have shown amplified spontaneous emission behaviors.
