合成以三唑並喹喔啉及三唑並吡啶為核心之對稱型螢光染料: 雙態螢光與放大自發輻射性質探討;Synthesis of Symmetric Fluorescent Dyes Based on Triazoloquinoxaline and Triazolopyridine: Dual-State Photoluminescence and Amplified Spontaneous Emission Properties Investigation

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题名:	合成以三唑並喹喔啉及三唑並吡啶為核心之對稱型螢光染料: 雙態螢光與放大自發輻射性質探討;Synthesis of Symmetric Fluorescent Dyes Based on Triazoloquinoxaline and Triazolopyridine: Dual-State Photoluminescence and Amplified Spontaneous Emission Properties Investigation
作者:	高筠貽;Kao, Yun-Yi
贡献者:	化學學系
关键词:	封面;論文授權書;延後公開申請書;推薦書;摘要;目錄;正文;參考文獻
日期:	2025-08-16
上传时间:	2025-10-17 11:30:22 (UTC+8)
出版者:	國立中央大學
摘要:	本篇研究成功合成出一系列Donor-Acceptor-Donor結構為基礎之對稱型有機螢光染料，並探討其雙態螢光 (Dual-State Emission, DSE)及放大自發輻射 (Amplified Spontaneous Emission, ASE)性質，進而評估其作為固態光電元件材料之應用潛力。在第一系列中，採用區域異構化 (Regioisomeric)，與延長π共軛系統的三唑並喹喔啉 (Triazoloquinoxaline)作為受體核心，以及階梯型芴 (Ladder-Type Fluorene)單元作為供體基團組合之。透過氮氣雷射激發所進行溶液態之放大自發輻射實驗結果顯示，模型分子(2)為本系列表現最佳者 (E_Th^ASE89.8 μJ ⋅cm-2)。此外，藉由微調核心結構，可實現波長可控性且光學表現相似的染料。未來此分子設計策略對於相關功能性材料的開發具有指導意義。第二系列，由本實驗室碩士班畢業生卓書澤學長所合成的三唑並吡啶 (Triazolopyridine)核心之染料，並由本校光電系張瑞芬教授實驗團隊進行薄膜態之放大自發輻射測試。結果顯示，模型分子(10)擁有最佳的性能表現 (E_Th^ASE78 μJ ⋅cm-2)。進一步將其作為客體材料 (Guest Material)，分別與兩種市售主體材料 (Host Material): PFO (Polydioctylfluorene)與CBP (4,4’-Bis(N-carbazolyl)-1,1’-biphenyl))，以及本研究合成之有機小分子螢光染料D2-4Ph製成三種摻混膜。證實了螢光共振能量轉移效應 (Fluorescence Resonance Energy Transfer, FRET)有效促進了放大自發輻射性質的增益現象，並同時說明了本研究合成染料與市售材料作為主體材料之應用潛力。 ;This study successfully synthesized a series of symmetric organic fluorescent dyes based on a Donor-Acceptor-Donor (D-A-D) structural framework and investigated their dual-state emission (DSE) and amplified spontaneous emission (ASE) properties, thereby evaluating their potential for application in solid-state optoelectronic devices. In the first series, regioisomeric modification and π-conjugation extension were employed, utilizing triazoloquinoxaline as the core acceptor and ladder-type fluorene units as donor groups. Solution-phase ASE experiments excited by a nitrogen laser revealed that model compound (2) exhibited the best performance in this series, with a threshold energy (E_Th^ASE) of 89.8 μJ ⋅cm-2. Moreover, by fine-tuning the core structure, dyes with tunable emission wavelengths and comparable optical properties were achieved. These findings provide valuable insights into molecular design strategies for the development of related functional materials. The second series involved dyes featuring triazolopyridine as the acceptor were synthesized by our former member (Mr. Shu-Tse, Cho). Thin-film ASE measurement was conducted by Prof. Rui-Fen, Chang’s research team in the Department of Optoelectronics at our university. The results indicated that model compound (10) delivered superior performance, with a threshold energy (E_Th^ASE) of 78 μJ ⋅cm-2. This compound was subsequently applied as a guest material and doped into three different host matrices: two commercially available PFO (polydioctylfluorene), CBP (4,4’-Bis(N-carbazolyl)-1,1’-biphenyl), and an organic small-molecule fluorescent dye (D2-4Ph) synthesized in this study. Experimental data confirmed that fluorescence resonance energy transfer (FRET) significantly enhanced ASE gain characteristics. Furthermore, the synthesized dyes demonstrated promising application potential relative to conventional commercial host materials.
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