開發具D-π-A 結構型態之雙光子螢光探針 與其雙態螢光性質探討

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姓名

吳承霖(Cheng-Lin Wu) 查詢紙本館藏

畢業系所

化學學系

論文名稱

開發具D-π-A 結構型態之雙光子螢光探針與其雙態螢光性質探討
(Development of Two-Photon Fluorescence Probes with D-π-A Structure and Investigation of Dual-State Emission Properties)

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摘要(中)

本論文成功引入苯碸(Phenyl Sulfone)、惡二唑(Oxadiazole)及二苯基甲酮(Benzophenone)等單元為拉電子基團並合成出不同系列之不對稱螢光分子，鑑定其在溶液態、固態之線性光學性質及溶液態非線性光學性質，同時也嘗試將這些結構用作螢光探針分子開發。經一系列實驗並分析其光學性質與分子結構間的關聯性後，我們可歸納出以下結論：
(1)以D-π-A形式設計出的不對稱螢光分子於溶液態有良好量子產率與明
顯溶劑效應，此種分子結構適合用作發展螢光探針。
(2)以Phenyl Sulfone合成出之螢光分子相較於以Oxadiazole合成出之螢
光分子有較明顯溶劑效應，也有較大的斯托克斯位移(Stokes
Shift)，在作為對極性敏感螢光探針應用上有更優秀的潛力。
(3)以Oxadiazole合成出之螢光分子相較於以Phenyl Sulfone合成出之螢
光分子於非線性光學性質上，有更高之雙光子吸收截面。
(4)以Benzophenone作為拉電子結構單元合成出之螢光分子明顯於固態
時有良好的螢光量子產率。
(5)於細胞實驗中證實，分子上的烷氧鏈過多可能會導致細胞標定胞器的
專一性不好，而Succinimidyl Ester 官能基團可以成功應用於免疫
染色顯影。

摘要(英)

Several series of novel asymmetric chromophores based on phenyl sulfone, 1,3,4-oxadiazole and benzophenone has been synthesized and investigated for their linear optical property both in solid and solution phases. The two-photon absorption properties in solution phase were also characterized based on two-photon-excited fluorescence technique.
After analyzing of the relation between the molecular structures and the obtained optical properties, the following conclusions can be drawn:
(1)Asymmetric chromophores of D-π-A type exhibit good quantum yields and significant solvent effect in solution phase. These chromophores are suitable for the development of fluorescence probes.
(2)Chromophores based on phenyl sulfone structure exhibit pronounced solvent effect and larger Stokes shift compared to those based on 1, 3, 4-oxadiazole. These chromophores can be potential polarity-sensitive fluorescence probes.
(3)Chromophores based on 1, 3, 4-oxadiazole exhibit higher two-photon cross section compared to those derived from phenyl sulfone.
(4)Chromophores based on benzophenone demonstrate high photoluminescence quantum yields in their solid state. (Фsolid about 35%-51%)
(5)In cell imaging test, it has been demonstrated that excessive amount of alkoxy chains on the structure may result in poor selectivity for labeling cellular organelles. On the other hand, the succinimidyl ester functional group has shown potentiality in immunofluorescence staining.

關鍵字(中)

★ 雙光子
★ 螢光探針
★ 雙態發射

關鍵字(英)

★ Two-Photon
★ Fluorescence probe
★ dual-state emission

論文目次

中文摘要 i
Abstract ii
誌謝 iii
目錄 v
圖目錄 vii
表目錄 xi
第一章緒論 1
1-1 雙光子吸收材料歷史背景與研究發展 2
1-1-1 雙光子吸收過程及原理 2
1-1-2 雙光子吸收材料之發展與應用 6
1-1-3 雙光子吸收材料分子設計及文獻回顧 10
1-1-4 時域聚焦多光子激發顯微技術(TFMPEM)介紹 13
1-2 螢光探針簡介及發展 15
1-2-1 單光子螢光探針簡介及應用 15
1-2-2 螢光探針分子設計 19
1-2-3 雙光子螢光探針之發展及優勢 23
1-3 具雙態發射性質之螢光分子簡介 27
1-3-1 雙態發射研究起源 27
1-3-2 雙態發射原理與分子設計與文獻探討 30
1-3-3 雙態發射螢光分子之應用 37
1-4 研究動機與論文架構 40
參考文獻 41
第二章分子設計與合成 44
2-1 模型分子結構與分子設計 44
2-2 合成策略及流程 51
參考文獻 69
第三章光學性質探討 70
3-1 前言 70
3-2 模型分子在溶液態及固態的線性光學性質 75
3-3 模型分子在溶液態之雙光子光學性質 94
3-4 結果與討論 106
第四章細胞影像實驗 110
第五章實驗儀器與藥品 117
5-1 合成實驗所使用之藥品及溶劑 117
5-2 光學實驗及光學儀器詳述 120
5-3 模型分子之詳細合成步驟 128
第六章結構鑑定光譜圖 177

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指導教授

林子超(Tzu-Chau Lin)

審核日期

2023-8-17

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