博碩士論文 952203046 詳細資訊




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姓名 徐正昇(Cheng-Sheng Hsu)  查詢紙本館藏   畢業系所 化學學系
論文名稱 新型雙光子吸收材料的分子設計與合成及其光學性質的探討
(Synthetic Strategies toward Indenofluorene Derivatizable with High Two-Photon Absorption)
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摘要(中) 本論文主要設計與合成新型雙光子吸收材料並探討其光學性質。我們將具有良好共平面性與發光性質的indenofluorene與fluorene導入本論文中的模型分子系統,透過小心的合成與純化鑑定的過程,成功地製備出數個條型、多叉型以及樹狀型的模型分子。在線性光學性質的量測上,我們使用吸收光譜儀與螢光光譜儀來量測模型分子的最大吸收波長、最大發射波長與螢光產率。另外,我們以可調節波長的(鈦:藍寶石)飛秒雷射作為探測光源針對這些模型分子來進行其非線性光學性質的量測。由所測得的雙光子激發螢光光譜以及雙光子螢光光強與入射光強度之依賴性等實驗數據顯示這些模型分子在光譜範圍700 nm至760 nm附近有明顯的雙光子吸收行為。經系統性比較這些模型分子之雙光子激發截面,我們得到三個結果:第一,改變條型分子之共軛長度同時觀察其雙光子吸收度的變化,我們發現延伸分子的共軛長度對提升分子的雙光子吸能力有很大的幫助。第二,由分析多叉型及樹狀型的模型分子之雙光子吸收行為觀察到當π-電子非定域化的範圍隨共軛系統的往多方向延伸而擴展時,分子的雙光子吸收能力也有非常明顯的提升。第三,本論文的模型分子系統經平行比較後我們觀察到含有indenofluorene的模型分子其展現的雙光子吸收能力是優於含 fluorene的類似模型分子。
摘要(英) The projects involved in this thesis mainly attempted to design and synthesize some novel two-photon absorbing model compounds and investigate their optical properties. The two-photon-absorption-related properties of these model compounds were characterized by using high peak power infra-red laser pluses working in femto-second regime. By analyzing the correlation between the model compounds and the observed two-photon absorption properties, we have concluded some useful information for the molecular design: First, it is observed that the molecular two-photon absorptivity can be promoted by extending of the π-conjugation length in our compound system. Second, two-photon absorption property can be effectively enhanced if the π-delocalization domain can be properly expanded. Third, the parallel comparison of the all analogues in our model compound system indicates that indeno- fluorene is a better two-photon activity enhancer over fluorene.
關鍵字(中) ★ 雙光子吸收材料
★ 雙光子
★ 多光子
關鍵字(英) ★ two-photon
★ two-photon absorbing
論文目次 目錄
中文摘要
英文摘要
謝誌
目錄...........................Ⅰ
圖表目錄.........................Ⅴ
附圖目錄.........................Ⅶ
第一章 序論 .......................1
1-1 簡介 .......................1
1-1-1 歷史背景簡述 ..................1
1-1-2 雙光子吸收材料之分子設計回顧 ..........2
1-1-3 雙光子吸收材之基本原理 .............4
1-2 雙光子吸收材料之前瞻性 ..............5
1-3 研究動機及本論文的組成..............11
第二章 分子設計與合成探討 ................13
2-1分子設計 .....................13
2-2目的物的合成與討論 ................19
2-2-1 目標物之結構式 .................19
2-2-2 逆合成分析 ...................22
2-2-3 合成策略及流程 .................26
第三章 光學性質探討..................40
3-1 線性光學性質..................40
3-1-1線性吸收之量測..................40
3-1-2單光子螢光發射光譜之量測.............45
3-1-3各模型分子之相對螢光量子產率(ΦF) ........47
3-2 非線性光學性質 .................49
3-2-1 雙光子激發螢光之量測 ..............49
3-2-2 雙光子激發螢光與激發光源強度關係的量測 .....52
3-2-3 雙光子螢光激發光譜的量測 ............58
3-3 結論 ......................73
第四章 實驗部份 ...................76
 4-1 實驗藥品及溶劑 .................76
4-2 實驗儀器及量測方法 ................77
4-3合成步驟......................78
化合物(1)之合成....................79
  化合物(2)之合成....................80
化合物(3)之合成....................80
化合物(4)之合成....................81
化合物(5)之合成....................82
化合物(6)之合成....................82
化合物(7)之合成....................83
化合物(8)之合成....................83
化合物(9)之合成....................84
化合物(10)之合成 ...................84
化合物(11)之合成 ...................84
化合物(12)之合成 ...................85
化合物(13)之合成 ...................87
化合物(14)之合成 ...................86
化合物(15)之合成 ....................86
化合物(16)之合成 ...................88
化合物(17)之合成 ...................89
化合物(18)之合成 ...................89
化合物(19)之合成 ...................90
化合物(20)之合成 ...................90
化合物(21)之合成 ...................91
化合物(22)之合成 ...................92
化合物(23)之合成 ...................93
化合物(24)之合成 ...................93
化合物(25)之合成 ...................94
化合物(26)之合成 ...................94
化合物(27)之合成 ...................95
化合物(28)之合成 ...................95
化合物(29)之合成 ...................97
化合物(30)之合成 ..................105
化合物(31)之合成 ..................106
TPA-IndFL-OXD之合成..................96
IndFL-2之合成.....................98
2TPA-IndFL之合成 ...................99
IndFL-4之合成 ....................100
IndFL-101D之合成 ..................101
DIndFL-OXD之合成 ..................102
2DIndFL-IndFL之合成 .................103
2DIndFL-FL之合成...................104
G1之合成.......................109
參考文獻 ........................110
附圖 ..........................116
圖表目錄
圖一. SUNY Buffalo之PNP研究團隊所提出的分子設計概念....2
圖二. AFX之分子示意圖 .................3
圖三. 單、雙光子吸收-發射螢光示意圖............4
圖四. 線性吸收與非線性吸收曲線示意圖 ...........6
圖五. 光學功率限制的示意圖 ................7
圖六. 雷射武器配置於戰機圖 ................8
圖七. 三維光學儲存記憶體示意圖 ..............9圖八. 單、雙光子激發之生物顯相示意圖...........10
圖九. 條形分子結構示意圖.................13
圖十. 四叉型分子結構示意圖................15
圖十一. 三叉型分子結構示意圖...............16
圖十二. 六叉型分子結構示意圖...............17
圖十三. 樹狀型分子結構示意圖 ..............18
圖十四. 對稱型條型分子結構圖及其代號...........19
圖十五. 非對稱型條型分子結構圖及其代號..........20
圖十六. 四叉型分子結構圖及其代號.............20
圖十七. 三叉型分子結構圖及其代號.............21
圖十八. 樹狀型分子結構圖及其代號.............21
圖十九. Cross- coupling reaction (Heck-suzuki reaction)反應
機制示意圖. ..................36
圖二十. Double Heck Reaction反應機制示意圖........39
圖二十一. 已畢業成員(陳昌鈺)合成之染料模型分子......43
圖二十二. 模型分子之線性吸收光譜圖............44
圖二十三. 模型分子之螢光發射光譜圖............46
圖二十四. 鈦:藍寶石雷射實體圖 ..............50
圖二十五. 雙光子之激發螢光量測裝置示意圖.........50
圖二十六. 雙光子之螢光光譜圖...............51
圖二十七. 雙光子的激發之螢光強度與激發光源強度間關係量測裝置示意圖....................53
圖二十八. 2DFL、FL-2、IndFL-2雙光子激發螢光強度與激發光
源強度關係圖..................54
圖二十九. 2DIndFL-FL、2DIndFL-IndFL、2TPA-IndFL雙光子
激發螢光強度與激發光源強度關係圖........55
圖三十. DIndFL-OXD、TPA-IndFL-OXD、FL-4雙光子激發
螢光強度與激發光源強度關係圖..........56
圖三十一. IndFL-4、101D、G1雙光子激發螢光強度與激發光源
強度關係圖...................57圖三十二. W.W. Webb之實驗設置示意圖圖 .........58
圖三十三. 雙光子之激發螢光光譜量測裝置示意圖.......60
圖三十四. Fluorescein激發螢光光譜圖............61
圖三十五. 對稱型條型分子之激發螢光光譜圖.........62
圖三十六. 非對稱型條型分子與四叉型分子之激發螢光光譜圖..63
圖三十七. 三叉型分子與樹狀型分子之激發螢光光譜圖.....64
圖三十八. 各模型分子之有效π-電子數與雙光子吸收特性之關聯圖.......................75
Scheme 1. Tripheylamnine之相關衍生物之合成流程圖.....27
Scheme 2. Fluorene之相關衍生物之合成流程圖........29
Scheme 3. IndenoFluorene之相關衍生物之合成流程圖.....31
Scheme 4. 2,5-diaryl-1,3,4-oxadiazole(化合物(28))之合成流程圖. 32
Scheme 5. TPA-IndFL-OXD之合成流程圖..........33
Scheme 6. 條型分子之合成流程圖 .............34
Scheme 7. 三叉型分子之合成流程圖 ............35
Scheme 8. 四叉型分子之合成流程圖 ............35
Scheme 8. 樹狀型分子之合成流程圖 ............38
表一. 模型分子之最大吸光係數、最大發射波長與螢光產率 ..48
表二. 所有模型分子之光學性質數據表 ...........68
附圖目錄
附圖一. 2DIndFL-FL之1H NMR(CDCl3)圖譜 .........117
附圖二. 2DIndFL-FL之13C NMR(CDCl3)圖譜.........118
附圖三. 2DIndFL-IndFL之1H NMR(CDCl3)圖譜........119
附圖四. 2DIndFL-IndFL之13C NMR(CDCl3)圖譜 .......120
附圖五. 2TPA-IndFL之1H NMR(CDCl3) 圖譜.........121
附圖六. 2TPA-IndFL之13C NMR(CDCl3) 圖譜 ........122
附圖七. IndFL-2之1H NMR(CDCl3) 圖譜 ..........123
附圖八. IndFL-2之13C NMR(CDCl3) 圖譜 .........124
附圖九. DIndFL-OXD之1H NMR(CDCl3) 圖譜.........125
附圖十. DIndFL-OXD之13C NMR(CDCl3) 圖譜 ........126
附圖十一. TPA-IndFL-OXD之1H NMR(CDCl3) 圖譜. .....127
附圖十二. TPA-IndFL-OXD之13C NMR(CDCl3) 圖譜......128
附圖十三. IndFL-4之1H NMR(CDCl3) 圖譜 .........129
附圖十四. IndFL-4之13C NMR(CDCl3) 圖譜.........130
附圖十五. IndFL-101D之1H NMR(CDCl3) 圖譜........131
附圖十六. IndFL-101D之13C NMR(CDCl3) 圖譜 .......132
附圖十七. G1之1H NMR(CDCl3) 圖譜............133
附圖十八. G1之13C NMR(CDCl3) 圖譜 ...........134
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指導教授 林子超(Tzu-Chau Lin) 審核日期 2008-7-20
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