三級膦催化烯炔化合物與碳六十的環加成反應與其衍生物應用於有機太陽能電池元件n型材料之效率探討

Abstract

本篇論文主要以探討三級膦與烯炔 (enyne)化合物的反應為主，為使用特定三級膦與烯炔化合物和碳六十反應。在其條件最佳化後，使用催化劑量的三級膦便能獲得不錯的產率。接著經由光譜分析、X光單晶繞射驗證，得知碳六十衍生物立體結構後，便可推斷可能反應機制。之後延長取代基碳鏈長度，增加其溶解度，將其應用到光伏打有機太陽能電池 (Organic Photovoltaic Cells, OPVs)上，進行效率量測，發現其中一個衍生物具有取代市面常用n型材料—PCBM的潛力。

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.