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研究生: 楊秉翰
Yang, Ping-Han
論文名稱: 含芘苯硼酸衍生物的合成及其性質之探討
Synthesis and Properties of a Pyrene Derivative with Boronic Acid
指導教授: 宋光生
Sung, Kuang-Sen
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2024
畢業學年度: 112
語文別: 中文
論文頁數: 71
中文關鍵詞: 芘衍生物π 堆積相互作用力硼酸脫硼
外文關鍵詞: pyrene derivative, π stacking interactions, boronic acid, deboronation
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  • 根據過去Theodor Agapie團隊32及Yamamoto團隊33的研究成果,我們設計出了一款能藉由N-B配位協助進行π堆積相互作用力的化合物,但在合成過程中,我們發現了意料之外的脫硼現象,因此,我們決定修改以吡啶當作底物的化合物,將之換成苯環結構,並在之後針對所合成出的化合物進行單晶繞射分析,雖然缺少了N-B配位的幫助,沒辦法提供較好的共平面結構,但結果是好的,該化合物的硼酸部分朝向是與芘同方向的,這對未來將其運用到與芳香環類化合物這類化合物結合時能產生π堆積相互作用力。

    Drawing on the research from Theodor Agapie's 32and Yohsuke Yamamoto's 33groups, we aimed to design a compound that could facilitate π-stacking interactions through N-B coordination. However, during the synthesis process, we encountered an unexpected deboronation phenomenon. This led us to modify the original design that used pyridine as the substrate, replacing it with a benzene ring structure. Subsequent single crystal X-ray diffraction analysis of the newly synthesized compound revealed that although it lacked the N-B coordination which might have offered a better coplanar structure, the results were positive. The orientation of the boronic acid part was aligned with the pyrene, which is advantageous for inducing π-stacking interactions when interacting with aromatic ring compounds in future applications.
    This modification not only addressed the deboronation issue but also preserved the compound's potential for effective π-π interactions, which are crucial for the intended applications in sensing and interaction with aromatic compounds.

    中文摘要 i Summary ii 誌謝 xix 目錄 xx 表目錄 xxi 圖目錄 xxi 第一章 緒論 1 I-1 前言 1 I-1-1 π–π 堆積相互作用 1 I-1-2 堆積二聚體 3 I-1-3 π–π 分子內堆積相互作用 4 I-1-4激基複合物 5 I-1-5 π–π堆積相互作用的應用 5 I-2 硼酸 5 I-3 Suzuki-Miyaura Reaction 7 I-4 研究動機 9 第二章 結果與討論 10 II-1 (2(6-(pyren-1-yl)pyridin-2-yl)phenyl)boronic acid之合成 10 II-2 具有N-B配位的芳基π共軛之螢光增益 11 II-3 意外的四配位的硼化物脫硼過程 12 II-4 化合物(3'-(pyren-1-yl)-[1,1'-biphenyl]-2-yl)boronic acid (11)之合成 14 II-5 化合物(3'-(pyren-1-yl)-[1,1'-biphenyl]-2-yl)boronic acid (11)之基本光譜性質 15 II-6 化合物(3'-(pyren-1-yl)-[1,1'-biphenyl]-2-yl)boronic acid (11) 晶體結構 19 II-7 結論 20 第三章 實驗儀器與實驗步驟 21 III-1 實驗儀器及測量方法 21 III-2 螢光產物之合成方法 22 III-3 UV-Vis吸收光譜測量及計算之方法 28 III-4 螢光光譜儀測量及螢光量子產率計算之方法 28 III-5 螢光量子產率標準溶液配置 29 第四章 參考文獻 30 附錄 34

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