Phosphine-Catalyzed Cycloaddition of Enynes with [60]Fullerene and Efficiency Study of Photovoltaic Devices with Obtained Fullerene Derivatives as n-Type Materials

• Main Authors: Tseng, Po-Yen, 曾柏諺
• Other Authors: Chuang, Shih-Ching
• Format: Others
• Language: zh-TW
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/78955131092961139054

碩士 === 國立交通大學 === 應用化學系碩博士班 === 102 === In this thesis,we provided a catalytic way to synthesis fullerene derivatives. By using triclohexyl phosphine cycloaddition of enynes with [60]fullerene to give cyclopentenofullerenes in good to excellent yields, through initial chemo- and regioselective 1,4-Michael nucleophilic conjugate addition of phosphines at the carbon of enyne substrates. The resulting cyclopentenofullerenes , characterized with spectrometric methods and single crystal X-ray diffraction analysis, exhibit higher LUMO energy levels than a typical n-type material, [6,6]-phenyl-C61 butyric acid methyl ester (PCBM). We next evaluated the power conversion efficiency (PCE) through enhanced solubility of cyclopentenofullerenes with long carbon chain. One of the fullerene derivatives gave 4.62% of PCE and 0.69V to Voc, which meant it had the possibility to substitute PCBM as n-type material in the future.