D?π?π?D 功能型芳香(雜)環寡聚物 之簡易兩步驟合成法開發研究;An Undemanding Two-Step Synthetic Pathway to D?π?π?D Type Functional Oligo(hetero)aryls

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题名:	D?π?π?D 功能型芳香(雜)環寡聚物之簡易兩步驟合成法開發研究;An Undemanding Two-Step Synthetic Pathway to D?π?π?D Type Functional Oligo(hetero)aryls
作者:	田昊旻;Tian, Hao-Min
贡献者:	化學工程與材料工程學系
关键词:	銅催化劑;直接碳氫鍵芳香環化反應;Copper catalyst;Direct C-H arylation
日期:	2021-08-19
上传时间:	2021-12-07 11:25:05 (UTC+8)
出版者:	國立中央大學
摘要:	材料是人類生存和社會發展的物質基礎，隨著科技的日新月異人們對於新材料的依賴也日漸增加，這使得開發新型材料的研究逐漸受到重視，而這當中又以有機光電材料的開發最受矚目，由於其具備輕薄短小、軟性可撓、材料多變的優點，現今已廣泛地應用於日常生活中可見的手機、電視螢幕等電子產品中，具有相當大的發展潛力。在眾多有機光電材料分子中，有一種 D?π?π?D 型的直線型小分子(D: electron donors; π: π?linker)，其作為有機發光材料與電洞傳輸材料在光電元件中皆擁有不錯的表現，然而其製備方法大部分仍然是以多步驟的傳統人名反應為主，此製備方法的步驟冗長、還需要使用到危險性較高的強鹼與對環境不友善的有機金屬試劑，這使得製備成本昂貴，並不是一個理想的合成策略。因此本研究團隊嘗試開發新型的兩步驟合成法，經由直接碳氫鍵芳香環化與自身耦合反應，高效率地合成出一系列新型 D?π?π?D 化合物，有效縮短合成步驟並改善傳統合成法的缺點。在本篇工作中我們使用了低價的銅金屬作為催化劑，透過嘗試不同溫度、配位基、鹼與溶劑，來找到最佳的反應條件，並且經由此銅催化直接碳氫鍵芳香環化反應合成出不同的電子 D?π 型式化合物，緊接著再進行自身耦合反應合成出 D?π?π?D 化合物 HMT01-08，最後我們對此八種化合物進行熱性質、光化學性質與電化學性質的量測與探討，並預計將其作為電洞傳輸材料應用於鈣鈦礦太陽能電池中，觀察其元件的效率表現。;Materials are the foundation for human survival and the development of civilization. With the rapid development of science and technology, people’s reliance on new materials is also increasing, which makes the development of new materials gradually get more attention. Among them, the development of organic optoelectronic materials attracts the most attention. Due to its lightness, thinness and shortness, flexibility and variable materials, it has been widely used in electronic products such as mobile phones and TV screens that can be seen in daily life, and has great potential for development. Recently, we find a D?π?π?D type linear organic small molecules, which have an excellent performance when it work as Light-emitter and hole-transporting Materials. However, most of them are synthesized by the traditional name reaction that requires not only tedious synthetic step but also using dangerous strong base and non-ecofriendly organometal reagent. Therefore, we report a new high efficiency two-step synthetic route via direct C-H arylation and homo-coupling to synthesize a series of D?π?π?D type linear oligo(hetero)aryl materials, which effectively shorten the synthesis steps and improve the disadvantages of traditional synthesis method. In this work, We used low cost copper as catalyst and optimized the reaction conditions of copper-catalyzed direct C-H arylation by screening different kinds of temperature, ligand, base and the solvent. Finally we used this copper-catalyzed direct C-H arylation and homo- coupling synthesize HMT01-08, Finally we measured their thermal properties, photovoltaic, and electrochemical characteristics. And use it as a hole transport material in the perovskite solar cell to investigate the efficiency of its components.
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