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研究生:麥綺倫
研究生(外文):Chi-Lun Mai
論文名稱:A:具有架橋基之雙紫質分子開關 B:應用於染料敏化太陽能電池之雙紫質合成與特性
論文名稱(外文):A:Synthesis of Porphyrin Dimers Bridged by an Electrochemically Switchable Unit B:Synthesis and Characterization of Diporphyrin Sensitizers for Dye-Sensitized Solar Cells
指導教授:葉鎮宇
指導教授(外文):Chen-Yu Yeh
口試委員:鄭淑華林敬堯郭明裕曾炳墝
口試委員(外文):Shu-Hua ChengChing-Yao LinMing-Yu KuoBiing-Chiau Tzeng
口試日期:2010-07-28
學位類別:博士
校院名稱:國立中興大學
系所名稱:化學系所
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:2010
畢業學年度:98
語文別:中文
論文頁數:387
中文關鍵詞:分子開關紫質染料敏化太陽能電池
外文關鍵詞:Molcular swicthporphyrinDye-Sensitized Solar Cells
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我們成功的合成具有quinone、dimethoxybenzene、anthraquinone 與diacetoxyanthracene 為架橋基的雙紫質與單紫質,並利用其電子吸收光譜、電化學方法以及化學氧化之吸收光譜來研究雙紫質系統中電子偶合的現象,其中Ni25 與Ni35都展現出在porphyrin 與porphyrin之間有很強的電子偶合現象,比較以anthraquinone-bridged Ni27 與quinone-bridge dimer Ni37,電子分佈在HOMO時分別定域化 (localized) 在兩側紫質單元間,因此,我們可以利用化學方法或電化學方法進行氧化還原反應來控制分子的開(switch on)與關(switch off)來應用在分子導線或電子材料上。

我們合成了三個具有推拉電子基的鋅紫質染料(YD11-YD13)應用在敏化太陽能電池(DSSC)上,而這些染料是利用酸基與TiO2做連結,其中最值得注意的是YD-12在相同條件下,不加入散射層與N719的光電轉化率比較分別為η= 6.7% 與 η= 6.1%;再加入散射層後雖然能提高N719的效率,但同時也能些微的提高YD系列的光伏性質,另外在雙紫質系列方面我們成功的合成具有很寬廣的吸收峰且延伸到近紅外光範圍;其中以meso–meso做連接的的雙紫質YDD1光電轉換率在1.5G的模擬太陽光下高達5.2%。我們相信以紫質為主體的
色素染料將來會有更佳的光電轉化效率的表現。
The synthesis of porphyrin dimer and monomer with a quinone, dimethoxybenzene、anthraquinone or diacetoxyanthracene unit has been achieved. Electrochemical and UV-Vis absorption measurements on these compounds show that the diacetoxyanthracene-bridge Ni25 and dimethoxybenzene-bridge Ni35 confers stronger porphyrin-porphyrin electronic communication. Comparing with the anthraquinone-bridged Ni27 and quinone-bridge dimer Ni37 system, the electron density of the HOMO is essentially localized on the two porphyrin rings and the LUMO is mainly contributed. The quinone and anthraquinone-bridged system can be reversibly switched from cross conjugated (switch off) to linear conjugated (switch on) via two-electron reduction/oxidation reactions. This feature holds promise for the quione-based wires to be used as redox-controlled switches in molecular electronic devices.

Three push–pull zinc porphyrins sensitizers (YD11–YD13) were synthesized for use as photosensitizers in TiO2 dye-sensitized solar cells. YD12 (η= 6.7%) is a green sensitizer remarkable for its outstanding cell performance beyond that of N719 (η= 6.1%) with no added scattering layer; the additional scattering layer assists N719 in promoting the effciency in the red shoulder of the spectrum, but has only a small effect on the improvement of the cell performance for porphyrins and Novel porphyrin dimers with broad and strong absorption in the visible and/or near IR regions have been synthesized; the meso–meso-linked porphyrin dimer (YDD1) exhibited the best photovoltaic performance with power conversion efficiency 5.2% under AM 1.5G one solar illumination. We believe that porphyrin-based DSSCs with even higher efficiency can be obtained.
第一章 具有架橋基之雙紫質分子開關
1-1 紫質(porphyrin)簡介...................................1
1-2 紫質性質............................. ................4
1-3 多紫質陣之分子導線與分子開關之簡介...................13
1-4 研究動機與方向.......................................25
1-5 紫質雙聚體之合成部分.................................26
1-5-1 紫質合成及其衍生物之合成...........................26
1-5-2 Anthraqinone 之合成................................31
1-5-3 具有架橋基Anthraqinone之雙紫質合成.................33
1-5-4 Dimethoxybenzene之架橋基合成.......................35
1-5-5 具有架橋基qinone之雙紫質合成.......................36
1-6 結果與討論 ..........................................41
1-6-1 Diacetoxylanthracene系列之UV-Vis吸收光譜...........42
1-6-2 Diacetoxylanthracene系列之電化學特性...............44
1-6-3 Diacetoxylanthracene系列之化學氧化還原吸收光譜之研究...............47
1-6-4 Dimethoxyphenylene系列之UV-Vis吸收光譜.............51
1-6-5 Dimethoxyphenylene系列之電化學特性.................52
1-6-6 Dimethoxyphenylene系列之晶體解析...................57
1-6-7 Dimethoxyphenylene系列之分子及軌域計算模型.........58
1-6-8 Dimethoxyphenylene化學氧化還原吸收光譜之研究.......59
1-7 結論.................................................62
1-8 未來展望.............................................64
1-9 實驗部分.............................................65
1-9-1 藥品與儀器.........................................65
1-9-2 實驗步驟...........................................70
第一章參考文獻...........................................92

第二章染料敏化太陽能電池之紫質
2-1 染料敏化太陽能電池的發展與起源.......................95
2-2 染料敏化太陽能電池簡介...............................99
2-3 染料敏化太陽能電池相關文獻回顧......................103
2-4 研究動機與方向......................................117
2-5 合成部分............................................119
2-5.1 紫質染料及其衍生物之合成..........................119
2-5.2 雙紫質染料之合成..................................121
2-5.3 鋅紫質染料之合成..................................125
2-6 雙紫質系列之結果與討論..............................134
2-6.1 雙紫質系列之UV-Vis光譜比較........................134
2-6.2 雙紫質系列之分子及軌域計算模型....................136
2-6.3 雙紫質系列之電化學分析............................138
2-6.4 雙紫質系列之染料敏化太陽能電池之結果與討論........144
2-6.5 雙紫質系列之染料敏化太陽能電池之結論..............147
2-6.6 雙紫質系列之染料敏化太陽能電池之未來與展望........148
2-7 YD系列紫質之結果與討論..............................149
2-7.1 YD系列紫質之UV-vis光譜比較........................149
2-7.2 YD系列紫質之電化學分析............................151
2-7.3 YD系列紫質之染料敏化太陽能電池之結果與討論........155
2-7.4 YD系列紫質之染料敏化太陽能電池之結論..............162
2-7.5 YD系列紫質之染料敏化太陽能電池之未來與展望........163
2-8 實驗部分............................................164
2-8.1 實驗步驟..........................................164
第二章參考文獻..........................................193
附錄一..................................................195
附錄二..................................................348
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