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研究生:陳柚全
研究生(外文):Yu-Chuan Chen
論文名稱:單硫紫質衍生物的合成及光電轉換效率研究
論文名稱(外文):Synthesis of Thiophene Containing Thiaporphyrin Derivativesand their Application as Photo-sensitizing Dyes
指導教授:洪政雄洪政雄引用關係
指導教授(外文):Chen-hsiung Hung
學位類別:碩士
校院名稱:國立中央大學
系所名稱:化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2008
畢業學年度:97
語文別:中文
論文頁數:111
中文關鍵詞:染料染料敏化太陽能電池光電轉換率單硫紫質紫質
外文關鍵詞:solar cellsdsscthiaporphyrinsporphyrins
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本研究主要目的為研發新穎染料分子-單硫紫質化合物,將其應用於染料敏化太陽能電池並分析效能上的影響,我們將單硫紫質結合酸基利用相關非對稱合成文獻合成出10-(4-carboxyphenyl)-5,15,20-tris(p-tolyl)-21-monothiaporphyrin (8)、10,15-bis(4-carboxyphenyl)-5,20-bis(p-tolyl)-21-monothiaporphyrin (9)、
5,10,15,20-tetra(4-carboxyphenyl)-21-thiaporphyrin (13) 與推電子基3,4,5-trimethoxylbenzene 置入的單硫紫質化合物
10,15-bis(4-carboxyphenyl)-5,20-bis(3,4,5-trimethoxyphenyl)
-21-monothiaporphyrin (19),也將以上化合物的性質和光譜鑑定做初步探討。另外我們首度成功合出和鋅金屬化的Zinc(II) complex (20),也做了單晶X-ray 繞射分析。由偵測光電轉換效率實驗結果顯示,化合物8、9、13、19 的光電轉換率分別為0.11%、0.07%、0.06%、0.12%,化合物9 和19 的比照中發現經由推拉電子基設計的染料分子其光電轉換效率可提升約71%,因此推測取代基的推電子和立體結構特性,能降低染料分子在TiO2 上產生堆疊效應及電荷重組的可能,使電子能夠有效在染料和半導體導帶間進行傳遞。我們嘗試將附著酸基單硫紫質化合物的TiO2 film,利用第二次浸泡含有2,6-lutidine 的ZnCl2 溶液方式和鋅進行金屬化反應,經Uv-vis 光譜做初步分析和探討。
The purpose of this research is to synthesize novel molecular dyes that possess a potential of applying on the fabrication of dye-sensitized solar cells. Synthesis and
spectroscopic characterization of asymmetric free-base thisaporphyrins that are attached by various numbers of carboxylic acid and electron donating groups, 10-(4-carboxyphenyl)-5,15,20-tris(p-tolyl)-21-monothiaporphyrin (8),10,15-bis(4-carboxyphenyl)-5,20-bis(p-tolyl)-21-monothiaporphyrin (9), 5,10,15,20-tetra(4-carboxyphenyl)-21-thiaporphyrin (13), and 10,15-bis(4-carboxyphenyl)-5,20-bis(3,4,5-trimethoxyphenyl)-21-mono-thiaporphyrin (19), have been achieved. Moreover, the first zinc(II) thiaporphyrin complex (20) has also been successfully prepared, and the structural characterization was unambiguously corroborated with single-crystal X-ray diffraction analysis. From the measured result of solar energy to electricity conversion efficiency (η), the h values are 0.11, 0.07, 0.06, and 0.12% for compounds 8, 9, 13, and 19, respectively. With introduction of electron donating groups, 3,4,5-trimethoxylphenyl, into the skeleton of thiaporphyrin 9, the push-and-pull functional thiaporphyrin molecule (19) can be highly promoted ca. 71% on η value. By means of modification with push-and-pull
and steric crowded groups, the possibility of molecular aggregation as well as charge recombination could be decreased, i.e. the electronic communication between a
molecular dye and the conductive band of TiO2 could be improved. On the other hand, zinc metallation of thiaporphyrin molecules has been directly carried out on the surface of TiO2 film, which was attached by thiaporphyrin molecules, by monitoring the shift on the Uv-vis spectrum.
章節 頁次
摘要
Abstract
謝誌
第一章 緒論 1
1-1. 紫質化合物簡介 1
1.2. 紫質衍生物 3
1-3. 紫質電子吸收光譜原理 3
1-4. 太陽能源的重要性 4
1-5. 太陽能電池的傳統發電原理 5
1-6. 染料敏化太陽能電池 6
1-7. 染料敏化太陽能電池工作原理 7
1-8. 染料敏化劑 8
1-9. 太陽能電池的重要參數 11
1-10. 研究動機與方向 12
第二章 單硫紫質的合成 15
單硫紫質染料及其衍生物的合成 15
第三章 實驗結果與討論 27
第四章 結論 88
第五章 未來展望 90
第六章 實驗步驟 91
參考文獻 110
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