含有醯胺基團之乙炔蒽衍生物：取代基團位置對於有機凝膠之形成及固態刺激響應行為之研究

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姓名

郭婷怡(Ting-Yi Kuo) 查詢紙本館藏

畢業系所

化學學系

論文名稱

含有醯胺基團之乙炔蒽衍生物：取代基團位置對於有機凝膠之形成及固態刺激響應行為之研究
(Ethylanthracene Derivatives with Amide-functional group：Investigation of Gel formation and Stimuli-responsive Behavior in Solid state with Different Substitute group.)

相關論文

★ 含有醯胺基團之乙炔蒽衍生物：碳氫長鏈與碳氟長鏈對於有機凝膠之形成及固態刺激響應行為之研究	★ 2,3位置含長鏈吡啶二醯胺基團之蒽衍生物：碳橋基及碳鏈長度對於有機凝膠形成及固態刺激響應性質之研究
★ 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 (2025-8-20以後開放)

摘要(中)

我們合成了含有醯胺基團之乙炔蒽衍生物，以不同取代基團（FB10、FB14）去探討其形成凝膠的能力與固態刺激響應行為。在形成凝膠能力的測試中發現FB10、FB14在許多有機溶劑中皆可以形成凝膠，而且具有良好的形成凝膠能力，其中FB14在1-heptanol中形成凝膠的能力最好，臨界凝膠濃度為2.71 mg/mL。以變溫吸收光譜、放射光譜及不同狀態下的吸收、放射光譜探討其分子間作用力及光物理變化，得知會形成聚集及分子間自組裝主要以J-type aggregation 形式進行；利用 1H NMR了解凝膠分子形成凝膠主要是以分子間的氫鍵、-作用力及 C-H···作用力而成。透過SEM 的觀察，其凝膠分子會自組裝排列成纖維結構或球形結構，其中FB10在p-xylene經由快速冷卻與慢速冷卻過程所形成的凝膠會有不同的微觀結構，FB10與FB14在不同溶劑中也能呈現網狀、細絲狀或球狀的微觀結構。在固態行為研究中，我們利用PXRD來探討形成乾凝膠後的堆疊模式，並對FB10與FB14的粉末進行刺激響應行為測試，其中發現FB10的B form粉末對於熱與機械力的刺激有良好的響應行為，FB14則是可以利用溶劑沉澱形成與原始粉末不同堆疊模式的粉末，對酸蒸氣也有響應行為的表現。

摘要(英)

We synthesized two anthracene-based organogelators, FB10 and FB14, respectively, containing long-chain perfluoro-alkoxyl and pyridine dicarboxamide function groups. These gelators are able to transform into organogels, when it presented in different organic solvents. As indicated inside the thesis, when it comes to comparing the properties between FB10 and FB14, the latter exhibits a better ability to form stable gel inside the 1-heptanol (the critical gelation concentration was 2.71 mg/mL). After in-depth investigation, we found that in the presence of perfluoroalkyl chain not only plays a key role in forming gel, but also influences their physical properties. A variety of spectroscopic methods were applied to identify the intermolecular interactions upon gel formation and explore the photo-physical properties. The primary driving forces for the gel formation are intermolecular hydrogen bonding, aromatic π-π, and C-H-πinteractions. The supramolecular aggregates in these organogels are considered to be J-type aggregation. SEM morphologies on the xerogels reveal that the gelators can self-assemble into fibers or spheres. On the other hand, when the gelator, FB10, went through rapid and slow cooling process signifying different SEM morphologies, when it dissolved in p-xylene (which has an ability to form gel). The gel formed by FB10 and FB14 in different solvents can also present filament, fibers or spheres on SEM morphologies. Moreover, we utilized PXRD to explore the stacking mode of xerogels as well as testing the stimulus response behavior between FB10 and FB14. Finding B form powder of FB10 have both interesting thermochromism and piezochromism behaviors；FB14 can use solvent to precipitate forming powder with different stacking mode from the original powder and possess acidochromism behavior.

關鍵字(中)

★ 有機凝膠分子
★ 超分子自組裝
★ 固態刺激響應行為材料
★ 蒽
★ 醯胺

關鍵字(英)

★ Organogels
★ supramolecular self-assembly
★ solid-state stimuli-responsive behavior
★ anthracene
★ amide

論文目次

中文摘要 I
英文摘要 II
誌謝辭 III
目錄 IV
圖目錄 VI
表目錄 XI
化合物對照表 XII
一、緒論 1
1.1 前言 1
1.1.1 凝膠的定義 2
1.1.2 凝膠的形成 2
1.1.3 凝膠的分類 3
1.2 小分子有機凝膠 4
1.3 小分子有機凝膠分類 5
1.3.1 含有碳氫鏈、碳氟鏈的有機凝膠 6
1.3.2 含有amide的有機凝膠 12
1.3.3 含有芳香環的有機凝膠 14
1.3.4 含有蒽的有機凝膠 18
1.3.5 含有金屬的有機金屬凝膠 24
1.3.6 多組分的有機凝膠系統 27
1.4 刺激響應 31
1.4.1 具刺激響應行為的分子 31
1.5 研究動機 36
二、結果與討論 38
2.1 實驗流程 38
2.2 凝膠分子FB10、FB14光物理性質 46
2.3 凝膠分子FB10、FB14的自組裝行為 50
2.3.1 不同溶劑下形成凝膠能力的測試 50
2.3.2 變溫核磁共振實驗 54
2.3.3 變溫UV-Vis 吸收實驗、變溫放射實驗 58
2.3.4 稀薄溶液、凝膠、薄膜狀態的吸收及放射實驗 62
2.3.5 分子聚集形貌研究 67
2.3.6 FB10、FB14與實驗室近年開發之凝膠分子比較 73
2.4 固態行為研究 77
2.4.1 Xerogel堆疊模式探討 77
2.4.2 刺激響應行為測試 80
2.4.3 熱穩定分析 89
三、結論 92
四、實驗部分 93
4.1 分析儀器 93
4.2 實驗藥品 97
4.3 實驗合成步驟 98
五、參考資料 112
六、附錄 120

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指導教授

孫世勝陳銘洲(Shih-Sheng Sun Ming-Chou Chen)

審核日期

2020-8-19

推文