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研究生： 王則彬
Tse-Pin - Wang
論文名稱： 合成具推拉電子基之苯乙烯芳烴分子及其光物理性質研究
Study on Synthesis and Photophysics of New Styrylarene Compounds with Electron Donor-Acceptor Groups
指導教授： 何郡軒
Jinn-Hsuan Ho
口試委員: 張家耀
Jia-Yaw Chang
鄭智嘉
Chih-Chia Cheng
學位類別： 碩士
Master
系所名稱： 工程學院 - 化學工程系
Department of Chemical Engineering
論文出版年： 2017
畢業學年度： 105
語文別： 中文
論文頁數： 203
中文關鍵詞： 分子內電荷轉移
外文關鍵詞： intramolecular charge transfer
相關次數： 點閱：272  下載：14 
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  •  上一筆

    • 在本研究中，針對了共軛系統為[n]phenacene的具推拉電子基分子作光物理性質的研究。

    [n]phenacene為多苯環芳香碳氫化合物分子，其共軛性佳且熱穩定性好，在本研究中，主要是以[n]phenacene為共軛系統合成一系列具推拉電子基的分子內電荷傳輸分子，本研究的推電子基為Triphenylamine，而拉電子基為-CN group，藉由具有顯著推拉電子能力的推電子基團與拉電子基團探討共軛系統之間共軛系統構形與共軛系統大小的差別。

    本研究藉由吸收光譜、螢光光譜與循環伏安法探討了最大吸收波長、最大放光波長、螢光量子產率、消光係數與HOMO/LUMO等光物理性質，藉由上述之測量與結果探討共軛系統與推拉電子基之間的差異，以幫助未來研發出更具前瞻性與實用性的材料。

    本研究以OLED光電材料為目的，開發了一系列的光電材料，這些材料具有應用在OLED的巨大潛力，本研究希望藉由這一系列的光電材料開發出更有效率及更環保的OLED元件，為地球環保盡一份心力。

    In this research, we focus on synthesis research and on photophysics property research of [n]phenacene derivative compounds that have electron-donor group and electron-acceptor group. These are four final compounds I discuss and research mainly.

    First, the research synthesizes four conjugated systems that are polycyclic aromatic hydrocarbon(PAHs) for their effective conjugation property and high thermal stability, and I choose triphenylamine as electron-donor group and cyanostyrene group as electron-acceptor group for their strong inductive effect.

    Second, the research measures and discusses many photophysical properties such as uv-visible absorption spectroscopy, fluorescence spectroscopy, fluorescence quantum yield, molar extinction coefficient and cyclic voltammetry, giving much information to let us know about these compounds properties and helping us to design the new compounds in the future.

    Finally, these compounds have potential on OLED application that are worth for us to think about it.

    摘要 I Abstract II 誌謝 III 目錄 V 圖目錄 IX 表目錄 XIV 前言 多芳香環碳氫分子及有機光電材料之簡介 1 第一章 緒論 7 第一節 有機發光二極體之發展與介紹 7 第二節 多芳香環碳氫分子應用於有機發光二極體之文獻回顧 10 第一項 Anthracene衍生化合物的相關發展 10 第二項 Chrysene衍生化合物的相關發展 14 第三項 Phenanthrene衍生化合物的相關發展 16 第四項 Naphthalene衍生化合物的相關發展 19 第五項 文獻回顧之總結 20 第三節 有機偶合反應之介紹 21 第一項 鈴木反應 21 第二項 赫克反應 22 第四節 分子光物理性質之理論介紹 23 第一項 分子內電荷轉移 23 第二項 溶劑效應 25 第三項 斯托克斯位移 26 第四項 偶極矩探討 27 第五項 螢光量子產率 28 第五節 研究動機及目的 29 第二章 結果與討論 31 第一節 化合物結構與代號 31 第二節 化合物於溶液中的光物理性質研究 32 第一項 F2L2於溶液中的光物理性質探討 32 第二項 F3L4於溶液中的光物理性質探討 35 第三項 F3W4於溶液中的光物理性質探討 38 第四項 F4W7於溶液中的光物理性質探討 41 第三節 化合物共軛系統對於光物理性質的影響 44 第一項 共軛系統對於最大吸收波長的探討 44 第二項 共軛系統對於螢光放光波長的探討 46 第四節 化合物於溶液中的吸收度 48 第一項 化合物於Acetone的吸收度 50 第二項 化合物於Acetonitrile的吸收度 52 第三項 化合物於Cyclohexane的吸收度 54 第四項 化合物於Dichloromethane的吸收度 56 第五項 化合物於Dibutylether的吸收度 58 第六項 化合物於Dimethylformamide的吸收度 60 第七項 化合物於Dimethyl sulfoxide的吸收度 62 第八項 化合物於Ethyl acetate的吸收度 64 第九項 化合物於Methanol的吸收度 66 第十項 化合物於Tetrahydrofuran的吸收度 68 第十一項 化合物於Toluene的吸收度 70 第五節 斯托克斯位移 72 第六節 分子內電荷傳遞效應與激發態偶極矩 73 第一項 利用Lippert-Mataga plot評估化合物的分子內電荷傳遞效應 73 第二項 激發態偶極矩 76 第七節 螢光量子產率 78 第八節 各化合物的電化學分析 82 第九節 理論計算與實際量測 89 第十節 各材料的熱性質分析 95 第三章 結論 96 第一節 結論 96 第二節 本研究的未來延伸 98 第四章 實驗部分 99 第一節 實驗儀器與器材： 99 第二節 儀器分析與原理 100 第一項 核磁共振光譜學 100 第二項 質譜儀 100 第三項 紫外光-可見光吸收儀 101 第四項 螢光光譜儀 101 第五項 循環伏安儀 102 第六項 熱重分析 102 第七項 差示掃描量熱法 102 第三節 實驗藥品與溶劑 103 第四節 紫外光-可見光光譜之量測 105 第五節 螢光光譜之量測 106 第六節 消光係數之量測 107 第七節 螢光量子產率之量測 108 第八節 氧化還原電位之量測 111 第九節 激發態偶極矩的計算方法 113 第十節 化合物的結構、名稱、代號、分子式與分子量 115 第十一節 化合物合成流程圖 119 第十二節 化合物之合成步驟 123 第五章 參考文獻 140 附錄 150

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