三級膦1,3-加成於烯炔類化合物與碳六十進行環加成反應與其衍生物應用於有機太陽能電池材料之效率探討

Abstract

本篇論文主要探討三級膦與烯炔類化合物的反應機制，並討論在三級膦的催化下，化合物3與碳六十進行反應時的情況。在設立最佳反應條件後，使用一系列烯炔類化合物與碳六十反應，並經由光譜分析與X-ray單晶繞射鑑定出碳六十衍生物的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，其表現與PCBM相當，具有成為新一代n型材料的潛力。

In this thesis, we revealed a phosphine-catalyzed [3+2] cycloaddition of compound 3 with [60]fullerene in a good yield. The reaction proceed through initial nucleophilic 1,3-addition of phosphine to alpha-carbon of 3 that forms reactive 1,3-dipoles followed by cycloaddition with [60]fullerene. The condition optimization, reaction scope, characterization and mechanism related to the formation of the proposed [60]fullerene products are also provided. The structures of these substrates are characterized spectrometrically 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. The selected fullerene derivatives were used as n-type materials in efficiency study of organic photovoltaic devices, and they show great potentials to be alternative n-type materials in the near feature.