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

• Main Authors: Jiung-Huai Huang, 黃泂淮
• Other Authors: Ching-Yuan Liu
• Format: Others
• Language: zh-TW
• Published: 2016
• Online Access: http://ndltd.ncl.edu.tw/handle/rrys7c

碩士 === 國立中央大學 === 化學工程與材料工程學系 === 104 === 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.