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姓名 李政穎(Jheng-Ying Li) 查詢紙本館藏 畢業系所 化學學系 論文名稱 含噻吩衍生物非對稱方酸染料應用於染料敏化 太陽能電池
(Unsymmetrical Squaraine Dyes Incorporating Electron-rich Thiophene Derivatives for Panchromatic Dye-Sensitized Solar Cells )相關論文 檔案 [Endnote RIS 格式]
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摘要(中) 由於全球暖化以及石化能源短缺的問題，使再生能源受到廣泛的注意。太陽能具有取之不盡，用之不竭的優勢，利用太陽能電池將光能轉為電能為眾所矚目的研究。染料敏化太陽能電池(dye-sensitized solar cells, DSSCs)具有透光性、可撓曲性、色彩多樣性、良好的光電轉換效率及低製造成本等優點，是目前相當熱門的研究領域之一，也是未來前景極為看好的新興科技。DSSCs中，光電流主要來源-光敏化劑(sensitizer)，是影響電池光電轉換效率以及元件穩定性的關鍵組成之一。DSSCs所採用的主要染料：以釕金屬為中心的錯合物以及有機共軛分子，皆具有高光電轉換效率(10-11 %)；僅管如此，這些染料仍無法有效的吸收遠紅光(far-red (FR) region)及近紅外光區(near-infrared (NIR) region)的光子，為了進一步的提高染料敏化太陽能電池的光電轉換效率，發展新型的FR/NIR染料是相當重要的。Squaraine染料具有高吸收係數且吸收的最大波長位於遠紅光/近紅外光區，是設計NIR染料的最佳選擇之一。本研究在設計合成幾個含squaraine單元染料分子:JYL-SQ1、JYL-SQ2、THL-SQ3、JYL-SQ5、JYL-SQ6及JYL-SQ7，採用donor-π-conjugated-acceptor的設計概念，同時以thiophene或其衍生物做為具有推電子能力的共軛片段來製備不對稱型squaraine染料，論文中詳細探討這些染料的物理性質，並將之組裝成DSSCs元件，測試元件的光電效能，以了解染料分子結構、物理性質與其所組裝之元件效率的關係。
摘要(英) Global warming and depletion of fossil fuels have led to a great interesting in clean renewable energy sources. Amongst the new energy technologies, solar cell which utilizes the Sun as an energy source is one of the most promising technologies. Dye-sensitized solar cell, DSSC, is considered as an alternative to the conventional solar cell due to its transparence, flexibility, colorfulness, high conversion efficiency and low cost. Sensitizer is one of the key components for the photovoltaic performance and long-term stability of DSSCs. Ruthenium complexes and organic dyes exhibit relatively high efficiency, however those photo-sensitizers did not absorb the photons in the Far-Red (FR) or Near-Infrared (NIR) region. To improve the performances of DSSCs, it would be essential to develop FR/NIR sensitizer. Squaraine dyes with attractively intrinsic absorption of the red-light photons and unusual high molar extinction coefficient were developed for the application in DSSCs. In this study we designed and synthesized several new donor-π conjugated- acceptor (D-π-A) unsymmetrical squaraine dyes, coded JYL-SQ1, JYL-SQ2, THL-SQ3, JYL-SQ5, JYL-SQ6 and JYL-SQ7, in which thiophene derivatives were incorporated to link the squaraine core and donor moiety. The fundamental physcicochemical properties of these squaraine dyes and the corresponding DSSCs devices based on them were well-studied. Understanding the relationship between the structure of the squaraine dyes, their physical properties and photovoltaic performance of the corresponding DSSCs devices may provide a new way for designing new high efficiency FR/NIR sensitizers.
關鍵字(中) ★ 方酸
★ 有機染料
★ 染料敏化太陽能電池
★ 噻吩關鍵字(英) ★ dye sensitized solar cells (DSSCs)
★ squaraine
★ thiophene
★ panchromatic論文目次 第一章.緒論 ............................................................................................................................... 1
1-1、前言 ................................................................................................................................ 1
1-2 染料敏化太陽能電池 ........................................................................................................ 3
1-3 染料敏化太陽能電池的組成及工作原理 ....................................................................... 4
1-4、光電轉換效率（Η（%））的量測 ............................................................................... 6
1-4-1、Overall conversion efficiency (η) ......................................................................... 6
1-4-2、IPCE (incident photon to current conversion efficiency) .................................... 7
1-5、光敏化劑 –染料 .............................................................................................................. 8
1-5-1、有機染料光敏化劑 (Metal-Free Organic Dye)概述 .......................................... 9
1-5-2、近紅外光染料 (Near-IR Dyes)概述 ................................................................. 16
1-6 研究動機 .......................................................................................................................... 26
第二章、實驗部分..................................................................................................................28
2-1、實驗藥品 ....................................................................................................................... 28
2-2、儀器分析與樣品製備 ................................................................................................... 33
2-2-1、紫外光/可見光及近紅外光吸收光譜儀；Ultraviolet/Visible and Near-Infrared Absorption Spectroscopy (Cary 300 UV/Vis Spectrometer).......................................... 33
2-2-2、螢光光譜儀;emission Spectroscopy (FluoroMax-4 spectro- fluorometer (HORIBA JOBIN YVON)) ....................................................................................... 33
2-2-3、紅外光吸收光譜儀;Infrared Abosrption Spectroscopy (Bio-rad FTS-155，FT-IR Spectrometer) ....................................................................................................... 34
2-2-4、液態核磁共振光譜儀；Solution State Nuclear Magnetic Resonance Spectrometer (Bruker DRX-300 MHz、Bruker DRX-500 MHz) ................................. 35
2-2-5、Electrochemical Measurement: 電化學測量裝置 (AUTOLAB PGSTAT30 電流/電位儀) ....................................................................................................................... 35
2-2-6、元件組裝與測詴: ............................................................................................... 36
2-3、實驗流程步驟 ............................................................................................................... 37
2-3-1、5-Carboxy-2-[[3-(5-methylthiophen-2-yl)-2-hydroxy-4-oxo-2-cyclo-buten-1- ylidene]methyl]-3,3-dimethyl-1-butyl-3H-indolium，JYL-SQ1之合成步驟 ............. 37
2-3-2、5-Carboxy-2-[[3-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)thiophen-2-yl)-2- hydroxy-4-oxo-2-cyclobuten-1-ylidene]methyl]-3,3-di- methyl-1-but- yl-3H-indolium， JYL-SQ2之合成步驟 ..................................................................................................... 38
2-3-3、5-Carboxy-2-[[3-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)-2,3-di-hydro- thieno[3,4-b][1,4]dioxin-7-yl)-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene]methyl]-3,3- dimethyl-1-butyl-3H-indolium，JYL-SQ5之合成步驟 ............................................... 39
2-3-4、5-Carboxy-2-[[3-(5-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl) thiophen-2-yl) thiophen- 2-yl)-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene]methyl]-3,3-dimethyl-1-butyl-3H-indolium，JYL-SQ6之合成步驟 ............................................................................ 40
2-3-5、5-Carboxy-2-{{3-{5-{5-{4-[N,N-Bis(4-hexyloxyphenyl)amino]phen-yl}-3,4- (ethylenedioxy)thiophene-2-yl}-4-hexylthiophene-2-yl}-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene}methyl}-3,3-dimethyl-1-butyl-3H-indolium，JYL-SQ7之合成步驟 ........ 41
2-4、合成步驟 ....................................................................................................................... 50
2-4-1、3,4-dichloro-3-cyclobutene-1,2-dione (簡稱SQ-Cl2)之合成 ............................ 50
2-4-2、2,3,3-trimethyl-3H-indole-5-carboxylic acid ( 簡稱TMCI)之合成 .................. 50
2-4-3、5-Carboxy-2,3,3-trimethyl-1-butyl-3H-indolium iodide (簡稱TMCI-b)之合成 ........................................................................................................................................ 51
2-4-4、3-chloro-4-(5-methylthiophen-2-yl)cyclobut-3-ene-1,2-dione (簡稱2-MT-SQ-Cl)之合成 ............................................................................................................................. 51
2-4-5、3-hydroxy-4-(5-methylthiophen-2-yl)cyclobut-3-ene-1,2-dione (簡稱2-MT-SQ- OH)之合成 ...................................................................................................................... 52
2-4-6、5-Carboxy-2-[[3-(5-methylthiophen-2-yl)-2-hydroxy-4-oxo-2-cyclo-buten-1- ylidene]methyl]-3,3-dimethyl-1-butyl-3H-indolium，JYL-SQ1之合成...................... 53
2-4-7、3,6-di-tert-butyl-9H-carbazole (簡稱DTBC)之合成 ......................................... 54
2-4-8、3,6-di-tert-butyl-9-(thiophen-2-yl)carbazole (簡稱T-DTBC)之合成 ............... 54
2-4-9、3-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)thiophen-2-yl)-4-chloro-cyclobut-3- ene-1,2-dione (簡稱Cl-SQ-T-DTBC)之合成 ................................................................. 55
2-4-10、3-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)thiophen-2-yl)-4-hydroxy-cyclobut- 3-ene-1,2-dione (簡稱HO-SQ-T-DTBC)之合成 ........................................................... 56
2-4-11、5-Carboxy-2-[[3-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)thiophen-2-yl)-2- hydroxy- 4-oxo-2-cyclobuten-1-ylidene]methyl]-3,3-dimethyl-1-butyl-3H-indolium， JYL-SQ2之合成 ............................................................................................................. 57
2-4-12、1-hexyloxyl-4-iodobenzene (簡稱h-IB)之合成............................................... 58
2-4-13、N, N-Bis(4-hexyloxyphenyl)-4-bromophenylamine (簡稱Br-TPA-Oh)之合成 ........................................................................................................................................ 58
2-4-14、2-{4-[N,N-Bis(4-hexyloxyphenyl)amino]phenyl}-3,4-(ethyl-enedioxy)thio- phene (簡稱ED OT-TPA-Oh)之合成 ............................................................................. 59
2-4-15、3-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)-2,3-dihydrothieno[3,4-b][1,4]- dioxin-7-yl)-4-chlorocyclobut-3-ene-1,2-dione (簡稱Cl-SQ- EDOT-TPA- Oh)之合成 ........................................................................................................................................ 60
2-4-16、3-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)-2,3-dihydrothieno[3,4-b][1,4]- dioxin-7-yl)-4-hydroxycyclobut-3-ene-1,2-dione (簡稱HO-SQ-EDOT-TPA-Oh)之合成 ........................................................................................................................................ 61
2-4-17、5-Carboxy-2-[[3-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)-2,3-dihydro- thieno[3,4-b][1,4]dioxin-7-yl)-2-hydroxy-4-oxo-2-cyclobuten-1-yl-diene]methyl]-3,3- dimethyl-1-butyl-3H-indolium , JYL-SQ5之合成 ........................................................ 62
2-4-18、trimethyl(5-(thiophen-2-yl) thiophen-2-yl) stannane (簡稱TMSn- BT)之合成 ........................................................................................................................................ 63
2-4-19、5-(5-(4-(N,N-Bis(4-hexyloxyphenyl)amino)phenyl)thiophene-2-yl)thiophene (簡稱BT-TPA-Oh)之合成 .............................................................................................. 63
2-4-20、3-(5-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophen-2-yl)thiophen-2- yl)-4-chlorocyclobut-3-ene-1,2-dione(簡稱Cl-SQ-BT -TPA-Oh)之合成 ..................... 64
2-4-21、3-(5-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phenyl)thiophen-2-yl)thiophen-2- yl)- 4-hydroxycyclobut-3-ene-1,2-dione (簡稱HO-SQ- BT-TPA -Oh)之合成 ............. 65
2-4-22、5-Carboxy-2-[[3-(5-(5-(4-(bis(4-(hexyloxy)phenyl)amino)phen- yl)thiophen-2- yl)thiophen-2-yl)-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene]methyl]-3,3-dimethyl-1- butyl-3H-indolium，JYL-SQ6之合成步驟 .................................................................. 66
2-4-23、trimethyl{2-{4-[N,N-Bis(4-hexyloxyphenyl)amino]phenyl}3,4-(ethylenedioxy) thiophene-5-yl}stannane之合成 ..................................................................................... 67
2-4-24、5-{5-{4-[N,N-Bis(4-hexyloxyphenyl)amino]phenyl}-3,4-(ethylene dioxy)thio- phene-2-yl}-4-hexylthiophene (簡稱3HT-EDOT-TPA-Oh)之合成 ............................. 68
2-4-25、3-{5-{5-{4-[N,N-Bis(4-hexyloxyphenyl)amino]phenyl}-3,4-(ethylenedioxy)- thiophene-2-yl}-4-hexylthiophene-2-yl}-4-chlorocyclobut-3-ene-1,2-dione (簡稱SQ-Cl-3HT-EDOT-TPA -Oh)之合成 ............................................................................ 69
2-4-26、3-{5-{5-{4-[N,N-Bis(4-hexyloxyphenyl)amino]phenyl}-3,4-(ethylenedioxy)- thiophene-2-yl}-4-hexylthiophene-2-yl}-4-hydroxycyclobut-3-ene-1,2-dione(簡稱SQ-OH-3HT-EDOT-TPA -Oh)之合成 .......................................................................... 70
2-4-27、5-Carboxy-2-{{3-{5-{5-{4-[N,N-Bis(4-hexyloxyphenyl)amino]phen- yl}-3,4- (ethylenedioxy)thiophene-2-yl}-4-hexylthiophene-2-yl}-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene}methyl}-3,3-dimethyl-1-butyl-3H-indolium，JYL-SQ7之合成 ................ 71
第三章、結果與討論 .............................................................................................................73
3-1、JYL-SQ1、JYL-SQ2 & THL-SQ3 ............................................................................... 73
3-1-1、JYL-SQ1、JYL-SQ2 & THL-SQ3的合成探討 ................................................ 73
3-1-2、JYL-SQ1、JYL-SQ2及THL-SQ3的光學性質與邊界軌域(frontier orbitals)分佈之理論計算探討 ............................................................................................................. 74
3-1-3、JYL-SQ1、JYL-SQ2 及THL-SQ3邊界軌域(frontier orbitals)之能階位置 ... 79
3-1-4、JYL-SQ1、JYL-SQ2及 THL-SQ3為敏化劑所組裝之元件的光電參數 ...... 82
3-2、JYL-SQ5 及JYL-SQ6 ................................................................................................... 85
3-2-1、JYL-SQ5 及JYL-SQ6的合成探討 ................................................................... 85
3-2-2、JYL-SQ5 及JYL-SQ6的光學性質探討與邊界軌域(frontier orbitals)分佈之理論計算探討 ..................................................................................................................... 85
3-2-3、JYL-SQ5 及JYL-SQ6邊界軌域(frontier orbitals)之能階位置 ....................... 90
3-2.3 以JYL-SQ5 及 JYL-SQ6為敏化劑所組裝之元件的光電參數 ....................... 92
3-3、JYL-SQ7 ........................................................................................................................ 94
3-3-1、JYL-SQ7的合成探討 ......................................................................................... 94
3-3-2、JYL-SQ7的光學性質探討 ................................................................................. 95
3-3-2、JYL-SQ7邊界軌域分佈及吸收光譜之理論計算 ............................................ 98
3-3-3、JYL-SQ7邊界軌域(frontier orbitals)之能階位置 ........................................... 100
3-3-4 以JYL-SQ7為敏化劑所組裝之元件的光電參數 ............................................ 101
結論 .......................................................................................................................................105
參考文獻 ...............................................................................................................................106
附錄 .......................................................................................................................................112
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