含醯胺官能基之蒽衍生物及其刺激響應行為之研究

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姓名

陳冠崴(Kuan-Wei Chen) 查詢紙本館藏

畢業系所

化學學系

論文名稱

含醯胺官能基之蒽衍生物及其刺激響應行為之研究

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至系統瀏覽論文 (2026-12-31以後開放)

摘要(中)

在本論文中，我們合成了一系列以蒽為主體的有機凝膠分子，並在分子中引入了醯胺官能基團。其中具有長碳鏈的結構分子 (1A12C、9A12C、1,4A12C) 具有形成超分子凝膠的特性，而我們的目標是了解這些分子的主要作用力是什麼，並探討分子間可能的自組裝模式。為了達到這個目的，我們使用了變溫的1H核磁共振 (NMR) 和紫外可見光譜 (UV-vis) 等技術。期望透過這些實驗，觀察到凝膠形成過程中的分子間作用力，包括分子間的作用力、π-π作用力和碳氫鍵(CH-π)作用力等。這些作用力對於凝膠的形成和穩定起著關鍵的作用。此外，我們還合成了具有短碳鏈結構的凝膠分子(1A4C、9A4C、1,4A4C)，並嘗試透過結晶生長來得到不同螢光性質的單晶，比較這些凝膠分子在固態下的刺激響應測試結果，讓我們能夠獲取得更多螢光變色的機制和分子自組裝行為的相關信息。
關鍵字：有機凝膠分子、超分子自組裝、蒽、醯胺、固態刺激響應、單晶

摘要(英)

In this research thesis, we synthesized a series of organic gel molecules based on anthracene and introduced acylamide functional groups into the molecules. The molecules with long carbon chains (1A12、9A12C、1,4A12C) exhibited the ability to form supramolecular gels. Our objective was to understand the primary forces driving gel formation and explore possible molecular self-assembly patterns. To achieve this, we employed techniques such as variable temperature 1H nuclear magnetic resonance (NMR) and ultraviolet-visible spectroscopy (UV-vis). Through these experiments, we aimed to observe the intermolecular forces involved in gel formation, including molecular interactions, π-π stacking, and CH-π interactions. These forces play a crucial role in the formation and stability of gels. Additionally, we synthesized gel molecules with short carbon chains (1A4C、9A4C、1,4A4C) and attempted to grow single crystals with different fluorescent properties. By comparing the results of solid-state stimulus response testing for these gel molecules, we aimed to gain insights into the mechanisms of fluorescence color changes and molecular self-assembly behavior.

Keywords: organogel molecules, supramolecular self-assembly, anthracene, amide, solid-state stimuli response, single crystal

關鍵字(中)

★ 有機凝膠分子
★ 超分子自組裝
★ 蒽
★ 醯胺
★ 固態刺激響應
★ 單晶

關鍵字(英)

★ organogel molecules
★ supramolecular self-assembly, anthracene
★ anthracene
★ amide
★ solid-state stimuli response
★ single crystal

論文目次

目錄
中文摘要 I
Abstract II
謝誌 III
目錄 IV
圖目錄 VIII
表目錄 XXIV
第一章序論 1
1-1. 前言 1
化合物對照表 2
1-2. 刺激響應的定義 4
1-3. 刺激響應材料 5
1-4. 凝膠的定義 17
1-4-1. 凝膠的種類 17
1-4-2. 超分子凝膠自組裝行為 18
1-5. 超分子有機凝膠 19
1-5-1. 含碳鏈的有機凝膠 19
1-5-2. 含醯胺官能基的有機凝膠 20
1-5-3. 含芳香環的有機凝膠 23
1-6. 刺激響應凝膠 26
1-7. 研究動機 31
第二章結果與討論 34
2-1. 實驗流程 34
2-2. 溶液下目標分子的吸收與放射 40
2-3. 不同溶劑的凝膠測試 54
2-4. 變溫核磁共振實驗 58
2-5. 變溫吸收和放射實驗 62
2-6. 掃描電子顯微鏡測試 69
2-7. 目標分子的刺激響應特性 77
2-7-1. 1A12C 刺激響應的性質 77
2-7-2. 1A4C 刺激響應的性質 79
2-7-3. 1A4C 青色螢光晶體 (BG) 83
2-7-4. 1A4C 黃綠色螢光晶體 (YG) 86
2-7-5. 9A12C 刺激響應的性質 91
2-7-6. 9A4C 刺激響應的性質 94
2-7-7. 9A4C 藍色螢光晶體 (B) 98
2-7-8. 9A4C 黃綠色螢光晶體 (YG) 101
2-7-9. 1,4A12C 刺激響應的性質 104
2-7-10. 1,4A4C 刺激響應的性質 108
2-7-11. 1,4A4C 藍色螢光晶體 (B) 112
2-7-12. 1,4A4C 綠色螢光晶體 (G) 116
第三章結論 118
第四章實驗部分 121
4-1. 分析儀器、實驗藥品 121
4-2. 實驗合成步驟 125
第五章參考資料 140
第六章附錄 144
6-1. 核磁共振光譜圖、質譜 145
6-2. ORTEP 圖 186
6-2-1. 1A4C 186
6-2-2. 9A4C 187
6-2-3. 1,4A4C 188
6-2-4. 9A4TC 189
6-3. 9A4C 熱刺激響應和 DSC 測量 191
6-4. 1A4C Photocycloaddition 192
6-5. 9A4TC 晶體排列 194
6-5-1. 9A4TC 不同晶體的放射光譜 194
6-5-2. 9A4TC 綠色螢光晶體 (G) 194
6-5-3. 9A4TC 青色螢光晶體 (BG) 195
6-5-4. 9A4TC 黃綠色螢光晶體 (YG) 195
6-6. 1A4C 青色螢光晶體之單晶資料 196
6-7. 1A4C 黃綠色螢光晶體之單晶資料 201
6-8. 9A4C 藍色螢光晶體之單晶資料 204
6-9. 9A4C 黃綠色螢光晶體之單晶資料 209
6-10. 1,4A4C 藍色螢光晶體之單晶資料 212
6-11. 1,4A4C 黃綠色螢光晶體之單晶資料 219
6-12. 9A4TC 青色螢光晶體之單晶資料 232
6-13. 9A4TC 綠色螢光晶體之單晶資料 235
6-14. 9A4TC 黃綠色螢光晶體之單晶資料 238

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指導教授

孫世勝陳銘洲(Shih-Sheng Sun Ming-Chou Chen)

審核日期

2023-8-19

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