銅催化之碳氫鍵芳香環化反應於染料敏化太陽能電池之綠色合成與應用;Step- and Cost-Effective Synthesis of D-π-A Organic Sensitizers via Cu-Catalyzed Direct Arylations: Development of Sn- & Pd-Free Process for Dye-Sensitized Solar Cells

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題名:	銅催化之碳氫鍵芳香環化反應於染料敏化太陽能電池之綠色合成與應用;Step- and Cost-Effective Synthesis of D-π-A Organic Sensitizers via Cu-Catalyzed Direct Arylations: Development of Sn- & Pd-Free Process for Dye-Sensitized Solar Cells
作者:	黃泂淮;Huang,Jiung-Huai
貢獻者:	化學工程與材料工程學系
關鍵詞:	染料敏化太陽能電池;Dye-Sensitized Solar Cells
日期:	2016-07-29
上傳時間:	2016-10-13 12:43:43 (UTC+8)
出版者:	國立中央大學
摘要:	有機染料敏化太陽能電池 (DSSCs)近年來發展非常快速，然而傳統合成染料分子的方法需要較多且繁雜的步驟。截至目前為止，僅有少數文獻利用具有步驟經濟效益之合成法來合成有機染料分子。其中具有步驟經濟效益之直接碳氫鍵芳香環化反應是一個非常具有競爭性的新合成法，此方法可將反應步驟從先前傳統人名反應中的四個步驟減少到僅需一個步驟即可完成。然而，目前直接碳氫芳香環化反應所使用之催化劑大部份都是利用昂貴的鈀錯合物。基於經濟成本考量，我們希望能找到便宜的催化劑來取代昂貴的鈀金屬催化劑。本研究此次準備以銅催化劑來取代鈀催化劑，開發出一套新的銅催化直接碳氫鍵芳香環化反應，並將合成之有機分子應用於DSSCs上。首先需尋找最佳化的反應條件，經過了篩選各式溶劑、配位基與鹼後得到最佳化反應條件。為證明此條件的適用性，於是嘗試變換各種推電子基團 (Donor)以及拉電子基團 (Acceptor)進行交叉耦合反應，且可成功合成出各類型之目標產物，證實此反應條件寬廣的應用性。本研究中將合成之有機染料分子應用於染料敏化太陽能電池 (DSSCs)，並展示了三條新型D-A-π-A以及D-π-A-π-A型之有機染料分子CYL-A、CYL-B以及CYL-C之合成，並測得其能源轉換效率 (PCE)為2.95-6.20 %。 ;In recent years, organic dye-sensitized solar cell (DSSCs) developed very fast, however, it requires complicated synthesis steps in using traditional method. So far, only a few literatures have been reported using direct C-H arylation synthesis method to synthesize small organic dye molecules. This method can only use one step to achieve the organic molecules we need, while the traditional method needs four steps. However, most of the literatures which study in C-H arylation method usually use palladium complexes as catalyst. But palladium complexes are expensive reagents, we hope to find out some other cheap reagents, which can replace it. In this report, we choose copper complexes as our catalyst in direct C-H arylation method. After screening various types of solvent, ligand and base, we finally find out the optimum reaction condition for our system. To demonstrate the applicability of this condition, we change different electron-rich and electron-deficient group in our system, and almost all the target product can be synthesized successfully. This confirms the broad applicability of the reaction conditions. For applications in dye-sensitized solar cells (DSSCs), we demonstrates three D-A-π-A type and D-π-A-π-A type new organic sensitizers (CYL-A、 CYL-B and CYL-C) can be step-economically synthesized via sequential C-H arylations using Cu catalyst .CYL-A、CYL-B and CYL-C give a Voc of 0.65-0.77 V, a Jsc of 5.17-12.60 mA/cm2, and a FF of 64.5-76.9 %, which corresponds to anoverall power conversion efficiency (PCE) of 2.51-6.20 %. This work is expected to become a practical synthetic alternative aiming at guiding material scientists to access small-molecule materials of interest with less synthetic transformations.
顯示於類別:	[化學工程與材料工程研究所] 博碩士論文

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