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研究生: 倪青文
Ching-wen Ni
論文名稱: 合成具苯乙烯基菲主骨架有機染料及研究 其光物理性質
Synthesize organic dye with styrylphenanthrene main backbone and study on their photophysical properties
指導教授: 何郡軒
Jinn-hsuan Ho
口試委員: 張家耀
Jia-yaw Chang
戴龑
Yian Tai
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: 2014
畢業學年度: 102
語文別: 中文
論文頁數: 146
中文關鍵詞: 苯乙烯基菲有機染料染料敏化太陽能電池
外文關鍵詞: styrylphenanthrene, organic dye, DSSC
相關次數: 點閱:242下載:4
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  • 本論文主要是開發新的有機染料,是以苯乙烯基菲為衍生物的染料,一個有機
    染料主要的基本結構上是具有拉電子基、π-共振橋基和推電子基三部份,而本論
    文的有機染料所使用的拉電子基是cyanoacrylic acid;π-共振橋基是苯乙烯基菲;
    推電子基是triphenylamine,而在已有的文獻上大部分是以苯乙烯或二苯乙烯為
    骨架衍生物研究居多,因此本實驗重新合成(Z)-2-cyano-3-(4-((E)-4-(diphenylami
    -no)syryl)phenyl)acrylic acid(CDSPA)是文獻上已有的化合物作為對照組,且本實
    驗室利用反式二苯乙烯照光經順式二苯乙烯進行六電子環化變成菲的光氧化環
    化反應,藉此成功合成出一系列的苯乙烯基菲衍生物,此結構增強了分子剛性及
    增加π 共軛系統,而對於苯乙烯基菲衍生物作為有機太陽電池的染料,目前是尚
    未有研究及討論的,因此本論文將對以苯乙烯基菲骨架的有機染料進行探討及研
    究。


    This paper aims to develop new organic dyes. The dye main backbone is
    styrylphenanthrene derivatives in this paper. A basic structure of the organic dye
    includes three parts: an acceptor, a π-electron resonance bridge and a donor. The
    acceptor of organic dye is the cyanoacrylic acid; the π-resonance bridge groups is
    styrylphenanthrene; their donor is the triphenylamine in this paper. However the most
    DSSCs dyes of the reported literature are based on styrene or derivatives of stilbene
    backbone, we synthesized the compound(CDSPA) as the counterpart. We used
    irradiated methodology to make trans-stilbene changing into cis-stilbene, which then
    carried out six-electron photocyclization to afford phenanthrene. By this feature, we
    have successfully synthesized a series of derivatives of styrylphenanthrenes, and their
    molecular structure strengthened the rigidity and increased more conjugated π system.
    Until now, no research in literatures studied styrylphenanthrene derivatives as DSSCs
    dye, therefore this paper will aim to synthesize organic dye with styrylphenanthrene
    main backbone and study on their photophysical properties.

    第一章 緒論…………………………………………………………………………01 1-1 前言……………………………………………………………………..01 1-2 DSSC 的光電轉換機制.……………………………………………...01 1-2-1 有機染料的基本結構…………………………………………….03 1-3 Jablonski 能階…………………………………………………………..03 1-3-1 分子電子躍遷…………………………………………………….05 1-3-2 有機光化學反應………………………………………………....06 1-4 分子內電荷轉移(ICT)………………………………………………….07 1-4-1 二苯乙烯類DSSCs 染料之文獻回顧…………………………09 1-5 研究動機與目的………………………………………………………..10 第二章 結果與討論………………………………………………………………....12 2-1 化合物合成方式之探討……………………………………………….12 2-2 不同溶劑下各化合物的UV和PL 圖…………………………………20 2-2-1 同溶劑下各化合物的UV比較圖………………………………23 2-3 各化合物的吸收度…………………………………………………….26 2-4 各化合物的偶極矩……………………………………………………29 2-5 各化合物的C-V 圖……………………………………………………31 2-6 各化合物的DSSC 效率……………………………………………..33 2-7 結論……………………………………………………………...……..34 2-8 未來展望………………………………………………………………..35 第三章 實驗部分……………………………………………………………………36 3-1 實驗儀器……………………………………………………………….36 3-2 實驗藥品與溶劑……………………………………………………….37 3-3 吸收度的測量方法…………………………………………………….39 3-4 偶極矩的計算方法……………………………………………………40 3-5 C-V 的測量及計算方法………………………………………………41 3-6 化合物結構、分子式及分子量表…………………………………….43 3-7 實驗流程圖…………………………………………………………….46 3-8 實驗步驟及化合物的化學位移……………………………………….49 第四章 參考文獻…………………………………………………………………...71 附錄…………………………………………………………………………74

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