臺灣博碩士論文加值系統

具有聚集誘導發光性質的材料近幾年吸引了很多人的興趣，因其在發光性質、光電元件、螢光探針、化學傳感及生物傳感上的應用。四苯乙烯是一種常被拿來討論具有顯著聚集誘導發光特性的化合物。本研究中成功合成出具有四邊取代基的四苯乙烯衍生物化合物9、14、15、16、18a-d來探討其吸收光譜、螢光光譜、聚集誘導發光現象、液態螢光量子產率和電化學性質。從化合物14、15的吸收、螢光光譜中得知共軛增長會產生紅移的現象。在聚集誘導發光測試中發現隨著不良溶液的增加，螢光強度會隨之增加，並產生些微紅移，並觀察出不同結構所產生不同螢光強度的變化。在螢光量子產率實驗中，加入三甲基矽基結構的化合物14為最高的56.7%，而不同烷基鏈對於螢光量子產率也有不同的影響。透過電化學則以循環伏安法測定出化合物的氧化電位，進而推定其最高佔據分子軌域(Highest occupied molecular orbital, HOMO)與最低未佔分子軌域(Lowest unoccupied molecular orbital, LUMO)的能階，並在熱重分析結果中顯示出化合物18a-d熱裂解溫度都於300oC以上，表現出良好的熱穩定性。

Luminescent materials with aggregation-induced emission (AIE) properties have attracted many people's interest in recent years due to their application in, optoelectronic components, fluorescent probes, chemical sensor, and biosensor. Tetraphenylethene (TPE) is a compound that often used to investigate luminescence properties with significant AIE. In this study, TPE derivatives 9, 14, 15, 16, 18a-d with tetra-substituted structure were successfully synthesized, and their absorption spectra, fluorescence spectra, aggregation-induced luminescence, liquid fluorescence quantum yield and electrochemical properties were studied. Based on the red-shift of absorption and fluorescence spectra for compounds 14, and 15, the conjugation growth was observed. In the aggregation-induced emission test, it was found that the fluorescence intensity increased with decrease of the solution solubility, and red-shift of fluorescence occurred. The compound 14, with Tetramethyl silane (TMS) substituents, showed the highest fluorescence quantum yield (56.7%). Moreover, different alkyl chains led to different fluorescence quantum yield. The oxidation potential of the compounds was determined by cyclic voltammetry and the energy of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) was estimated. The thermal decomposition temperatures of the compounds were above 300oC revealing good thermal stability.

致謝 II
摘要 III
Abstract IV
目錄 VI
圖目錄 VIII
表目錄 XIV
第一章 緒論 1
1.1研究動機 1
1.2研究目的 1
第二章 文獻回顧 2
2.1聚集誘導螢光猝滅與聚集誘導發光 2
2.1.1聚集誘導螢光猝滅 2
2.1.2聚集誘導發光 3
2.1.3 聚集誘導的發光機制 4
2.2 具有聚集誘導發光效應的四苯乙烯化合物應用 5
2.2.1 在有機發光二極體上的應用 5
2.2.2 在機械螢光變色材料上的應用 7
2.2.3 在危害物質檢測上的應用 8
2.2.4 在生物傳感及顯影上的應用 9
2.3 多重取代基與四苯乙烯化合物的關係 10
2.3.1含有單邊取代基的四苯乙烯化合物 10
3.2含有雙邊取代基的四苯乙烯化合物 16
2.3.3 含有四邊取代基的四苯乙烯化合物 20
2.4 文獻總結 24
第三章　實驗方法 25
3.1實驗藥品 25
3.2實驗步驟 27
3.3檢測儀器 46
3.4檢測方法 47
3.4.1吸收光譜儀 47
3.4.2螢光光譜儀 47
3.4.3液態螢光量子產率 47
3.4.4電化學測定儀 48
3.4.5超導磁場核磁共振儀 48
3.4.6 熱重分析儀 49
第四章 結果與討論 50
4.1合成結果 50
4.1.1 NMR光譜 50
4.2光物理性質 55
4.2.1吸收及螢光光譜圖 55
4.2.2聚集誘導發光性質 (AIE) 60
4.2.3液態螢光量子產率 71
4.3電化學分析 72
4.4熱重分析 79
第五章 結論 81
附錄 83
附錄一：氫核磁共振光譜 83
附錄二：碳核磁共振光譜 92
參考文獻 95

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