在複雜環境上量測物質或環境變化經常需要使用特定儀器，而使用螢光探 針作為量測媒介則可以簡化量測流程與工具，並可應用於可視化生物體內 各組織的狀況。 本篇論文成功以喹啉與稠合喹啉衍生物為主結構單元並合成出四個系 列的模型分子，藉由實驗量測其線性與非線性光學性質可以得知這些分子 具有以下特性: (1) 以 D-π-A 方式組成之第一、二、三系列條形分子有明顯溶劑效應。 (2) 對同一系列分子而言，在固定推電子基團的情況下，改變拉電子基 團共軛性質會影響螢光激發效率，相比於 benzothiazole，以 triazolopyridine 與 oxadiazole 做為拉電子基團雖在高極性溶劑具有較 高的螢光量子產率，但雙光子激發截面值皆較低。 (3) 第二系列分子在結構中引入烷氧基有助於提升螢光量子產率與雙光 子螢光表現，並在不改變共軛結構下於末端連接不同標定官能基不 會對螢光性質有顯著改變。 (4) 本篇論文中化合物雖然在溶劑態時具有優秀的螢光量子產率與亮 度，但在固態的螢光量子產率表現較差。 (5) 以雙鍵延長共軛系統導致在高極性溶劑下螢光量子產率降低，但對 於環境黏稠度的改變具有敏感性。 (6) 以含氮雜環結構作為共軛系統之螢光探針對於酸性環境具有敏感 性，並可於鹼性環境回復原有光學性質。;Detection of substances or environmental changes in a complex environment often requires specific instruments. However, using fluorescent probes as media can simplify the measurement processes and tools. And such probes can be applied to visualize the status of various tissues in living organisms. In this thiesis, four series of model compound were successfully synthesized using quinoline and fused quinoline derivatives as the main structural units. Through the experimental measurement of linear and nonlinear optical properties, it can be known that these molecules have the following characteristics: (1) Model compounds of D-π-A type show very salient solvent effect. (2) For the same series of molecules, keeping same electron-donating group while changing the electron-withdrawing group will affect the fluorescence efficiency. Compare to benzothiazole, using triazolopyridine or oxadiazole as electron-withdrawing groups lead to high fluorescence quantum yield in high polar solvent but low two-photon excitation cross section. (3) The introduction of alkoxy groups in the second series of model molecules can improve the fluorescence quantum yield and two-photon emission performance. In addition, attaching different bio-labeling functional groups to the aforementioned model structures does not change their fluorescent properties. iii (4) Although these final compounds have excellent fluorescence quantum yields and brightness in solvents, the fluorescence quantum yields of these compounds in the solid state are poor. (5) Extending the conjugated system with double bonds leads to a decrease in the fluorescence quantum yield in high polar solvents, but makes it sensitive to the viscosity. (6) Using heterocyclic units containing nitrogen as a part of conjugated systems can make fluorescent probes sensitive to the pH change of the environment and the process of fluorescence color change in accordance with the pH variation is reversible.
