合成及鑑定含口比啶及側邊烷氧取代基之三個芳香環共軛的螢光材料

Abstract

本實驗是以Heck reaction與Wittig reaction合成出一系列含口比啶及側邊烷氧取代基之三個共軛環的螢光材料，再與不同的質子予體酸製備成氫鍵錯合物。在熱性質方面，以熱重分析儀(TGA)、熱微差掃瞄分析儀(DSC)與偏光顯微鏡(POM)測得化合物的熱裂解溫度(Td)為327℃~396℃，並可觀察到當引入噁二唑時可增加其熱穩定性。而化合物的光學性質則由紫外光可見光光譜儀（UV/Vis)和螢光分光光譜儀測得，化合物在極稀的氯仿溶劑中所得到的最大吸收波長範圍為392~408nm;最大螢光（PL）放射波長為452~471nm，而在薄膜態以及電致放光光譜(EL)最大放射波長也皆在藍綠光範圍內，再由循環伏安(CV)法量測，引入不同的推、拉電子基團與置換不同的雜環分子可改變HOMO與LUMO的能階。最後在形成氫鍵錯合物時可觀察到較未配氫鍵前有明顯的紅位移。

In this study, a series of novel photoluminet materials containing three conjugated-rings with pyridine and alkoxy-substituted side groups were synthesized successfully by Heck and Wittig reaction and then H-bonded to several different proton donors containing carboxylic acids groups to form H-bonded complexes. The thermal properties of these materials were determined by TGA、DSC and POM. The onset decomposition temperatures (Td) of all compounds are among 327℃~396℃. Better thermal stability can be achieved by introducing oxadiazole moiety. The optical properties of these materials were determined by UV (uv-vis) and PL (photoluminescent). All of these compounds showed the maxaimum absorption in the range of 392~408 nm in diluted chloroform. All of these polymers in chloroform emit blue-green fluorescence around 452~471nm. In the film state, these materials also revealed that the emission wavelengths lie in the range of blue-green. From CV (cyclic voltage) measurement, it was able to adjust the energy gap of these compounds by modification of the end groups and conjugation length. The experimental results implied that the H-bonded interaction of the complexes could cause a red-shift and further red-shift. The emission peaks of these materials shifted by using of various acids as proton donors. Moreover, the emission color is easy to be tuned by H-bonding.