請用此 Handle URI 來引用此文件：
http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/72508完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 林金全(King-Chuen Lin) | |
| dc.contributor.author | Hsin-Lung Lee | en |
| dc.contributor.author | 李欣隆 | zh_TW |
| dc.date.accessioned | 2021-06-17T07:00:05Z | - |
| dc.date.available | 2024-08-13 | |
| dc.date.copyright | 2019-08-13 | |
| dc.date.issued | 2019 | |
| dc.date.submitted | 2019-08-02 | |
| dc.identifier.citation | Chapter 1
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/72508 | - |
| dc.description.abstract | 化學感測器（chemosensor）是對於特定物質有辨識能力以改變其感測器的光電性質並處理及轉換成訊號。金屬離子感測在環境汙染物的監測當今科技工業迅速發展的年代是對於生態永續發展非常重要的課題。尤其當越來越多的慢性疾病被發現與人體攝取過多的重金屬離子有相關性，化學研究學者已經發展出不同的方法去做金屬離子感測。例如，利用修飾電極表面以增加特定金屬離子的親和力來觀察電流或電位的變化；合成特殊結構的化合物，當化合物與特定金屬離子交互作用時可以使得系統產生光子訊號，已達到金屬感測的目的。金屬離子感測器的發展已經超過百年，新興物質的發展已經大幅提升金屬離子感測的靈敏度以及專一性。本研究主要目的在設計對金屬離子具有專一性的螢光感測分子材料。螢光感測分子材料主要使用冠狀醚（crown ether）作為金屬離子的辨識單元，並化學鏈結到不同的訊號輸出單元，包含羅丹明（rhodamine）、硒化鎘量子點（CdSe Quantum dots）、矽量子點（silicon quantum dots）、中孔洞二氧化矽奈米粒子（mesoporous silica nanoparticle），討論不同大小及不同雜環原子種類的冠醚分子對金屬離子選擇性。
實驗結果得到：第一、羅丹明-15-冠-5與硒化鎘量子點-15-冠-5共軛物（RBCE-QDCE）對於鉀離子能形成三明治錯合物，具有高效的螢光共振能量轉移（Förster resonance energy transfer, 44％）。第二、氮雜冠狀醚（aza-crown ether）修飾於矽量子點（SiQDs）表面，我們發現氮雜-15冠-5-矽量子點能夠專一選擇鎂離子、氮雜-18-冠-6-矽量子點專一選擇二價錳離子、二氮雜-18-冠-6-矽量子點專一選擇鈣離子。其原理是利用金屬離子對於氮雜冠狀醚有專一選擇性，而冠狀醚上的氮雜原子具有光誘導電子轉移（photoinduced electron transfer）性質能夠淬熄矽量子點的光致發光。第三、螺環內醯胺-羅丹明B鏈結不同大小環的冠狀醚（sRBCEs）分別對四價錫離子有螢光感測能力。第四、更進一步地，將螺環內醯胺-羅丹明B修飾上中孔洞分子篩（SBA-15-sRB）發現對於鋁離子有專一選擇性。螺環內醯胺-羅丹明B（Spiro-lactam Rhodamine B）能夠與金屬離子配位形成錯合物，並將原始羅丹明B的螢光恢復以達到螢光感測的效果，稱之螯合增強螢光（chelation-enhanced fluorescence）。 | zh_TW |
| dc.description.abstract | A chemosensor is a kind of molecular structure that is used for sensing of a specific analyte to produce a detectable change or a signal. Metal ion sensing in environmental pollutants monitoring is an important issue of sustainable development. While rapid industrial development, many diseases were found to be associated with excessive diet of metal ions. Chemists had developed vary of methods for metal ion sensing. For example, the modified electrode can increase the affinity of specific metal ions, and it can be observed changes in current or potential. Synthesized specific structure molecule can interact with a specific metal ion, and the molecule can transduce a photon signal, which has achieved the purpose of metal sensing. Metal ion sensors had been developed for many decades, and new materials was found and greatly improved the sensitivity and specificity of metal ion sensing. The main purpose of this study was to design a fluorescent sensing molecular material, which is specific to metal ions. Fluorescent sensing molecular materials mainly composed of crown ether as the identification unit of metal ions, and chemically bonded to different signal output units, including rhodamine B, CdSe Quantum dots, silicon quantum dots and mesoporous silica nanoparticles. The selectivity of the crown ether molecules using different sizes and different heterocyclic atom was discussed.
The experimental results show that: First, 15-crown-5-ether attached rhodamine B and 15-crown-5-ether capped CdSe/ZnS quantum dots conjugate (RBCE-QDCE) formed a sandwich complex with potassium ions by fluorescence resonance energy transfer (44%). Second, the aza-crown ether was modified on the surface of silicon quantum dots (SiQDs). It was found that the sensing of multiple metal ions including magnesium ion, manganese(II) ion and calcium ion by using diverse aza-crown ether-functionalized SiQDs based on the suppression of PET process and further demonstrate their sensing efficiency. Third, the chemosensor (sRBCEs) composed of rhodamine B with 15-crown-5/18-crown-6 can detect the tin(IV) ions and showed florescence recovery in the presence of these ions, respectively. Fourth, furthermore, the spirocyclic rhodamine B modified with SBA-15 (SBA-15-sRB) had showed specific selectivity for aluminium ions. Spiro-lactam rhodamine B can form a complex with metal ions, and then rhodamine B fluorescence recovered to achieve metal ion sensing, called chelation-enhanced fluorescence. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-17T07:00:05Z (GMT). No. of bitstreams: 1 ntu-108-D98223106-1.pdf: 9163836 bytes, checksum: 2407373d9d527c45b1d3b4333a91bed9 (MD5) Previous issue date: 2019 | en |
| dc.description.tableofcontents | 口試委員審定書 I
謝誌 III 摘要 V ABSTRACT VII CONTENT IX FIGURE CAPTIONS XV SCHEME CAPTIONS XXV TABLE CAPTIONS XXVII EQUATION CAPTIONS XXVIII ABERRATION TABLE XXIX CHAPTER 1 1 STUDY MOTIVES 1 REFERENCE 8 CHAPTER 2 21 INTRODUCTION 21 METHOD 25 Instrument 25 Synthesis 25 Preparation of 15-crown-5 ether attached rhodamine B 26 1) Boc-protection of 6-Aminocaproic acid 26 2) Synthesis of Boc-6-Ahx-15-Crown-5 28 3) Boc-deprotection of Boc-6-Ahx-15-Crown-5 30 4) Synthesis of RBCE 32 Preparation of 15-crown-5 capped QDs 34 1) Synthesis of (15-crown-5) LA 35 2) Synthesis of 15-crown-5 capped QDs (QDCE) 37 General procedure for sensing of metal ion 37 RESULTS AND DISCUSSION 38 CONCLUSION 54 REFERENCE 55 CHAPTER 3 66 INTRODUCTION 66 METHOD 70 Materials and Methods. 70 Synthesis of Aza-Crown Ether Capping Agents 71 1). Aza-15-crown-5 4-pentenamide. 72 2) Aza-18-crown-6 4-pentenamide. 75 3) Diaza-18-crown-6 4-pentenamide. 77 Synthesis of Aza-Crown Ether Functionalized Silicon Quantum Dots (SiQDs/CE) 79 General Procedure for Sensing of Metal Ions 80 Theoretical Method 82 Cell Culture 82 RESULTS AND DISCUSSION 83 Characterization of Aza-Crown Ether Functionalized Silicon Quantum Dots (SiQDs/CE) 83 Fluorescence Sensing of Metal Ions 86 CONCLUSIONS 106 REFERENCES 107 CHAPTER 4 119 INTRODUCTION 119 METHOD 122 Materials and Synthesis 122 Instrument 122 Synthesis of spiro-Rhodamine B 123 Synthesis of succinic acid mono crown ester (succinic acid mono15-crown-5 ester and succinic acid mono18-crown-6 ester) 126 1) Succinic acid mono15-crown-5 ester: 127 2) Succinic acid mono18-crown-6 ester: 128 Synthesis of sRBCE15 130 Synthesis of sRBCE18 133 General Procedure for Sensing of Metal Ions 136 Calculation for the association constant and the detection limit 137 Computational study details 138 Cell Culture 138 Cell Cytotoxicity 138 RESULTS AND DISCUSSION 140 Effect of pH values 140 Selectivity of sRBCEs 142 Sensitivity of sRBCEs 148 Structure study of sRBCEs with Sn4+ complex 153 Theoretical calculations 159 In vitro bioimaging and cytotoxicity of sRBCEs in the presence of metal ions 163 CONCLUSION 168 REFERENCE 169 CHAPTER 5 181 INTRODUCTION 181 METHOD 185 Materials and Methods. 185 Synthesis of spiro-Rhodamine B (sRB) 185 Synthesis of sRB-TEPI 188 Synthesis of SBA-15 191 Synthesis of SBA-15-sRB 191 Characterization 192 Detection of metal ions 192 Cell viability assay and imaging 193 RESULTS AND DISCUSSION 195 Characterization of SBA-15 and SBA-15-sRB 195 Photoluminescence properties of SBA-15-sRB 203 Cell studies 211 CONCLUSION 213 REFERENCE 214 CHAPTER 6 221 SUMMARY 221 PERSPECTIVES 223 | |
| dc.language.iso | en | |
| dc.subject | 金屬離子感測 | zh_TW |
| dc.subject | 冠狀醚 | zh_TW |
| dc.subject | 羅丹明B | zh_TW |
| dc.subject | 螢光共振能量轉 | zh_TW |
| dc.subject | 光誘導電子轉移 | zh_TW |
| dc.subject | 配位增強螢光 | zh_TW |
| dc.subject | metal ion sensing | en |
| dc.subject | photoinduced electron transfer | en |
| dc.subject | chelation enhanced fluorescence | en |
| dc.subject | crown ether | en |
| dc.subject | rhodamine B | en |
| dc.subject | fluorescence resonance energy transfer | en |
| dc.title | 合成冠狀醚—奈米材料衍生物應用於金屬離子感測之研究 | zh_TW |
| dc.title | Synthesis of crown ether-nanomaterial derivatives for application in metal ion sensing | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 107-2 | |
| dc.description.degree | 博士 | |
| dc.contributor.oralexamcommittee | 葉伊純(Yi-Cheun Yeh),黃志清(Chih-Ching Huang),江志強(Jyh-Chiang Jiang),廖尉斯(Wei-Ssu Liao) | |
| dc.subject.keyword | 金屬離子感測,冠狀醚,羅丹明B,螢光共振能量轉,光誘導電子轉移,配位增強螢光, | zh_TW |
| dc.subject.keyword | metal ion sensing,crown ether,rhodamine B,fluorescence resonance energy transfer,photoinduced electron transfer,chelation enhanced fluorescence, | en |
| dc.relation.page | 224 | |
| dc.identifier.doi | 10.6342/NTU201901377 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2019-08-05 | |
| 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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