有機膦促進炔與碳簇反應與其衍生物之應用探討

Abstract

本篇論文主要探討三級膦與烯炔類化合物的反應機制，使用三級膦作為催化劑與烯炔類化合物、碳六十進行反應。找尋到最佳反應條件後，變換各類型烯炔類化合物，合成一系列碳六十衍生物，並透過光譜分析與X-ray單晶繞射鑑定出其立體結構並推測其反應機構。將獲得的產物應用於有機太陽能電池n型材料，並量測光電轉換效率，若能找到適當混合比例和製成參數，有機會超越市面常用n型材料—PCBM。

In this thesis, we demonstrate a triphenylphosphine-catalyzed cycloaddition of methyl (Z)-3-methyl-7-phenylhepta-2-en-4,6-diynoates with [60]fullerene to give unusual cyclobutenofullerenes in good yields. The condition optimization, reaction scope, characterization and mechanism related to the formation of the proposed [60]fullerene products are also provided. The molecular structures of these cyclobutenofullerenes were characterized by mass spectrometry (MS), 1H and 13C NMR and infrared spectroscopic methods and supported by single crystal X-ray diffraction analysis. These derivatives possess a general trend of LUMO energy levels as the typical n-type material, PCBM does. In the second part of the thesis, the selected fullerene derivatives were utilized as n-type materials in efficiency study of organic photovoltaic devices, and some of them show good potentials to be an alternative n-type materials in the feature.