本論文成功合成出9個染料分子,可分為兩個系列,分別以三唑 并吡啶(Triazolopyridine)及吡啶并吡嗪 (Pyridopyrazine)為核心,於其兩端接上芴 (Fluorene)與茚並芴 (Indenofluorene)結構單元而組成對稱型的模型分子,並探討其在雙態螢光發射 (Dual-State Emission;DSE)、放大自發輻射 (Amplified Spontaneous Emission;ASE)與雙光子吸收 (Two-photon Absorption)等光學性質。 本論文合成的兩個系列模型分子在其溶液態量子產率皆有良好 表現 (ΦF=0.7−0.99),其中模型分子2、5、7在固態也有良好表現(分 別為ΦF =0.78、ΦF =0.71、ΦF =0.64 ),具有成為優異雙態螢光發射材 料潛力。同時我們發現此兩種不同核心,會對模型分子之螢光生命期 有明顯的影響。此外我們以337 nm 的氮氣雷射激發進行 ASE 測試 時,發現僅有以triazolopyridine 為核心之模型分子具有 ASE 性質, 其中模型分子5所表現出的閥值最低 (52.3 μJcm-2)。 另外,這些模型分子皆有雙光子活性,具有相當強度的雙光子螢 光。其中,模型分子5表現出δ = 1455 GM的雙光子激發截面值,而 模型分子8也表現δ = 888 GM的雙光子激發截面值。兩者皆有潛力 做為高效的雙光子螢光材料。;We have synthesized nine model molecules compounds using two types of nitrogen-containing heterocyclic structural units (tiazolopyridine and pyridopyrazine) as the central cores, which are end-capped by functionalized fluorene and indenofluorene units to form symmetric structures. All of these model compounds were investigated for their dual-state emission (DSE), amplified spontaneous emission (ASE), and two-photon absorption properties. All the studied model molecules showed good fluorescence quantum yields (ΦF=0.70.99) in solution phase. Among them, model molecules 2, 5, and 8 also show high fluorescence quantum yield in the solid state, indicating their potential as DSE materials. On the other hand, we have found that different cores can lead to significant variation in fluorescence lifetimes. It is also found that only the triazolopyridine series exhibit ASE properties, with model molecule 5 showing the lowest ASE threshold value (52.3 μJcm-2). As for the two-photon property studies, model molecule 5 exhibits two-photon cross-section value of δ = 1455 GM at 790 nm while model molecule 8 exhibits two-photon absorption cross-section value of δ = 888 GM at 840 nm, suggesting their potential as highly efficient two-photon fluorescent materials.