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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 楊吉水(Jye-Shane Yang) | |
| dc.contributor.author | Yu-Hsuan Hu | en |
| dc.contributor.author | 胡雨旋 | zh_TW |
| dc.date.accessioned | 2021-06-17T01:35:39Z | - |
| dc.date.available | 2025-08-25 | |
| dc.date.copyright | 2020-09-16 | |
| dc.date.issued | 2020 | |
| dc.date.submitted | 2020-08-25 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/67516 | - |
| dc.description.abstract | 刺激響應材料是具有智能行為的材料，它能夠感知外界環境如外力、溫度、蒸氣、光等刺激而產生可被偵測的變化量。以光作為刺激源的響應材料近年來備受關注。本實驗室近年發展了不同碳鏈長度修飾的五苯荑，並以蒽作為螢光團的化合物P(Cn)，其於固態下展現同質多晶形性，分別為Y型、G型、B型。在光刺激下Y型與G型皆會進行二聚合，並展現放光變色的現象；B型則沒有二聚合的發生。二聚合與晶格剛硬度的交互作用造成光機械應力，進而影響蒽蒽間的交互作用，使得晶體展現獨特的光色變化。此為文獻中前所未見的光致機械力放光變色 (photomechanofluorochromism, PMFC) 現象。 本論文根據本實驗室近年研究成果及文獻資料，分別在五苯荑的長碳鏈上或蒽上進行氟取代，設計出化合物P(F)、An(F)、An(F)P(F)。前兩種化合物展現同質多晶形性，為G型及B型，而後者化合物只具有G型。在光刺激下，三種化合物晶體呈現不盡相同的光色變化，其中P(F)的G型晶體形狀更隨著光刺激而有顯著變化，經紫外光照射後晶體彎離光源。對此進行晶體結構分析，來探討氟取代基在分子排列及晶體放光顏色上、形狀上所造成的影響。再進一步結合晶體結構、光物理參數、二聚合程度等數據，探討PMFC和光機械效應的現象，並進而提出在光刺激下晶體變化機制。以期氟取代基對固態刺激響應材料性質的影響對日後科學家在分子設計上有所幫助。 | zh_TW |
| dc.description.abstract | Stimuli-responsive materials are materials with intelligent behavior. They can sense the external stimuli such as external force, temperature, steam, light, and so on, by producing detectable signals. Among those stimuli, light have received much attention in recent years. In our previous work, we have synthesized P(Cn), a monosubstituted anthracene as the chromophore with pentiptycene moiety modified with different length of alkyl chain. They exhibited polymorphism in the solid state, including yellow fluorescence (Y form), green fluorescence (G form) and blue fluorescence (B form). Under light irradiation, the Y form and the G form underwent dimerization along with the change of fluorescence color while B form was unreactive. The fluorescence color change resulted from the interaction between dimerization and lattice rigidity. The interaction caused photomechanical stress, which in turn affected the interaction between anthracene moieties, making the crystal exhibit unique fluorescence color change. We named this “photomechanofluorochromism”, abbreviated as PMFC. Based on our research and the previous observation of others’ research, we designed P(F), An(F), An(F)P(F) derivatives by fluorine substitution on the alkyl chain or on anthracene. P(F) and An(F) exhibited polymorphism including a G form and a B form. An(F)P(F) only exhibited a G form. Under UV light irradiation, their crystals showed different fluorescence color change, and the shape of the P(F) G form crystal deformed significantly. The P(F) G form crystal bent away from the light source after irradiation. Therefore, the crystal structure analysis was carried out to investigate the effects of the fluoro substituents on the molecular arrangement, the fluorescence color, and the crystal shape. We further combined the data of crystal structure, photophysical parameters, and degree of dimerization to propose a mechanism to explain the change of crystal under light irradiation. By studying on these derivatives, we hope that the fluoro-substituent effect on the properties of solid-state fluorescent materials can pave the way for the molecular design toward better understanding of the PMFC properties. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-17T01:35:39Z (GMT). No. of bitstreams: 1 U0001-1508202016541100.pdf: 14830175 bytes, checksum: 38a2cb2f0413e60616112b5a8bbc5275 (MD5) Previous issue date: 2020 | en |
| dc.description.tableofcontents | 誌謝 I 摘要 II Abstract III 目錄 V 圖目錄 VIII 表目錄 XIV 附圖目錄 XV 附表目錄 XVII 第一章 緒論 1 1-1 有機氟化物的簡介 1 1-1-1 氟原子對有機物的影響 1 1-1-2 有機氟化物的分子間作用力 2 1-1-3 有機氟化物分子間作用力的應用 5 1-2 刺激響應材料 7 1-2-1 光響應材料 7 1-3 光響應分子晶體 12 1-3-1 常見分子晶體之光化學反應 13 1-3-2 拓樸化學 15 1-3-3 光致變色 17 1-3-4 光致放光變色 18 1-3-5 光致放光開關 21 1-3-6 光機械效應 23 1-4 含五苯荑基團之固態刺激響應材料 30 1-4-1 五苯荑分子的介紹 30 1-4-2 五苯荑於刺激響應材料的應用 31 1-5 研究動機 37 第二章 結果與討論 38 2-1 目標化合物的合成 38 2-1-1 目標化合物的逆合成分析 38 2-1-2 目標化合物P(F)的合成 39 2-1-3 目標化合物An(F)的合成 40 2-1-4 目標化合物An(F)P(F)的合成 41 2-1-5 化合物碳譜分析 41 2-2 目標化合物的溶液態光物理性質 43 2-2-1 目標化合物於二氯甲烷的吸收光譜 43 2-2-2 目標化合物於二氯甲烷的激發光譜與放光光譜 43 2-3 目標化合物的固態光物理性質 45 2-3-1 目標化合物的同質多晶形性檢測 45 2-3-2 G型目標化合物的固態光物理性質 46 2-3-3 B型目標化合物的固態光物理性質 47 2-4 目標化合物的光致機械力放光變色 49 2-4-1 目標化合物的PMFC性質測試 49 2-4-2 G型目標化合物的PMFC性質之探討 49 2-4-3 B型目標化合物的PMFC性質之探討 64 2-5 目標化合物P(F)的熱致回復性 68 2-6 目標化合物P(F)的G型晶體應用 70 第三章 結論 71 第四章 實驗部分 72 4-1 實驗藥品與溶劑 72 4-2 實驗儀器 75 4-2-1 核磁共振光譜儀 (Nuclear Magnetic Resonance) 75 4-2-2 高解析度質譜儀 (High Resolution Mass) 75 4-2-3 熔點測定儀 (Melting Point Apparatus) 75 4-2-4 紅外線吸收光譜儀 (FT-Infrared Spectrometer) 76 4-2-5 紫外光/可見光吸收光譜儀 (Ultraviolet/Visible Spectrophotometer) 76 4-2-6 螢光光譜儀 (Fluorescence Spectrometer) 76 4-2-7 X-光粉末繞射儀 (X-ray Powder Diffractometer) 78 4-2-8 X-光單晶繞射儀 (X-ray Single Crystal Diffractometer) 78 4-3 實驗方法 79 4-3-1 目標化合物粉末及晶體的製備 79 4-3-2 目標化合物晶體的光致機械力放光變色 80 4-3-3 二聚體定量分析 80 4-3-4 化合物P(F)晶體的光機械效應 81 4-3-5 化合物的合成 81 參考資料 92 附錄 97 | |
| dc.language.iso | zh-TW | |
| dc.subject | 氟取代基效應 | zh_TW |
| dc.subject | 光致機械力放光變色 | zh_TW |
| dc.subject | 蒽-五苯荑衍生物 | zh_TW |
| dc.subject | Fluoro-Substituent Effects | en |
| dc.subject | Photomechanofluorochromism | en |
| dc.subject | Anthracene-Pentiptycene Derivatives | en |
| dc.title | 氟取代基效應對蒽-五苯荑衍生物之晶體結構及光致機械力放光變色之探討 | zh_TW |
| dc.title | Fluoro-Substituent Effects on the Crystal Structure and the Photomechanofluorochromism of Anthracene-Pentiptycene Derivatives | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 108-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 孫世勝(Shih-Sheng Sun),詹益慈(Yi-Tsu Chan),陳志欣(Chih-Hsin Chen) | |
| dc.subject.keyword | 光致機械力放光變色,蒽-五苯荑衍生物,氟取代基效應, | zh_TW |
| dc.subject.keyword | Photomechanofluorochromism,Anthracene-Pentiptycene Derivatives,Fluoro-Substituent Effects, | en |
| dc.relation.page | 178 | |
| dc.identifier.doi | 10.6342/NTU202003527 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2020-08-26 | |
| dc.contributor.author-college | 理學院 | zh_TW |
| dc.contributor.author-dept | 化學研究所 | zh_TW |
| 顯示於系所單位： | 化學系 | |
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