數類含雜環結構單元之染料分子的合成與其雙光子吸收性質探討

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林哲儀(Jhe-Yi Lin) 查詢紙本館藏

畢業系所

化學學系

論文名稱

數類含雜環結構單元之染料分子的合成與其雙光子吸收性質探討
(Synthesis and Investigation of Two-photon Absorption Properties of Organic Molecules with Various Heterocyclic Structural Units)

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摘要(中)

本論文一共合成出三個系列的模型分子，第一系列為含有三個氮的六員雜環結構單元(三嗪；1,2,4-triazine)；第二系列為含有四個氮的六員雜環結構單元(四嗪；1,2,4,5-tetrazine)；第三系列則為具有不同拉電子強度之核心單元的雜環分子，如苯并噻二唑(benzothiadiazole)、喹喔啉(quinoxaline)、三唑(triazole)以及鄰苯二甲醯亞胺(phthalimide)，並藉由光學量測來比較各系列間結構上的差異所造成其線性與非線性光學性質上的差別。在線性光學性質探討部分我們量測了吸收光譜、螢光光譜、螢光量子產率與螢光生命期；而在非線性光學性質研究部分我們則是量測雙光子激發光譜與光學功率限幅。在雙光子激發光譜中，我們會以能量依賴性實驗來證實我們所看到的螢光確實為雙光子所誘導，進而利用螢光比較法計算出雙光子吸收截面；由以上的光學數據可歸納出以下結論：
[1] 本論文所研究的三嗪(triazine)衍生物在螢光量子產率的表現上皆不佳(量子產率範圍：0.002~0.24)。我們推測三嗪(triazine)衍生物其基態電子被激發到激發態後易以非輻射的方式釋放激發態能量，以至於本系列模型分子之螢光量子產率皆不高。
[2] 四嗪(tetrazine)與喹喔啉(quinoxaline)結合的衍生物擁有不錯的雙光子吸收性質，且有明顯的溶劑效應。
[3] 具有不同拉電子核心單元的條型模型分子都具有良好的雙光子吸收表現，其中以含有苯并噻二唑(benzothiadiazole)為核心的模型分子，其雙光子吸收表現最好。
本論文中也記錄了有關開發含高度共平面結構單元之染料分子的合成探討。藉由合成途徑的優化與修改，我們順利地得到目標前驅物。在這個計畫中我們嘗試優化實驗的條件、途徑以及產率，這些經驗可以作為未來繼續開發此類結構的基礎。

摘要(英)

In this thesis, we have successfully synthesized three series of model compounds with various heterocyclic structural units, and we have also compared their optical properties by linear and nonlinear optical experiments. For linear optical property studies, we have measured linear absorption spectra, fluorescence spectra, quantum yield and life time. For the nonlinear optical property studies, we have measured two-photon absorption spectra and two-photon-based optical power-limiting in the femtosecond and nanosecond regimes, respectively. In order to verify that the fluorescence we have observed is induced by two-photon absorption, we have performed the power-dependence experiment. Based on the collected optical data, some features can be noted:
[1] All of the triazine derivatives exhibit poor quantum yields, as we postulate that the excited state of the electrons release their energy by nonradiative pathways, so that such series of model compounds do not show strong fluorescence.
[2] The structure unit with fused tetrazine and quinoxaline units can promote the molecular two-photon absorption. These chromophores also possess salient solvatofluorochromism.
[3] The structure contains benzothiadiazole (BTD) unit that show excellent two-photon absorption.
In addition, we have also explored the synthetic procedures toward highly coplanar polyarene system based on phenanthrenequinone. We have tried to optimize the experimental conditions in order to increase the easy of synthesis and the yields. All the efforts devoted in this project have come out as valuable experience that may help the future investigation.

關鍵字(中)

★ 雙光子吸收
★ 發色團
★ 共軛
★ 光學功率限幅

關鍵字(英)

★ Two-photon absorption
★ Chromophores
★ Conjugation
★ Optical power-limiting

論文目次

第一章序論 1
1-1雙光子吸收理論及歷史演進 1
1-2雙光子吸收材料的相關應用 5
1-3雙光子吸收材料的分子設計及文獻回顧 6
第二章本論文模型分子的設計與合成 21
2-1本論文模型分子的設計概念 21
2-1-1含有三嗪(triazine)結構單元的模型分子 22
2-1-2含有四嗪(tetrazine)結構單元的模型分子 29
2-1-3具donor-acceptor-donor (D-A-D)性質的分子 32
2-2本論文模型分子的合成途徑 35
2-2-1第一系列：含有三嗪(triazine)結構單元的模型分子 35
2-2-2第二系列：含有四嗪(tetrazine)結構單元的模型分子 44
2-2-3第三系列：具donor-acceptor-donor (D-A-D)性質之模型分子 55
第三章光學性質探討 68
3-1光學實驗及光學儀器詳述 68
3-2模型分子線性及非線性光學數據 75
3-2-1第一系列：含有三嗪(triazine)結構單元的模型分子 75
3-2-2第二系列：含有四嗪(tetrazine)結構單元的模型分子 93
3-2-3第三系列：具donor-acceptor-donor結構單元之模型分子. 102
3-4各系列模型分子光學性質結果與討論 110
第四章 Phenanthrenequinone衍生物的合成及探討 114
4-1模型分子設計概念 114
4-2模型分子合成途徑 115
4-3模型分子後續發展 129
第五章實驗部分 133
5-1合成所使用的藥品及溶劑 133
5.2本論文化合物的合成詳細步驟 136
第六章附圖 227

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指導教授

林子超(Tzu-Chau Lin)

審核日期

2017-7-7

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