核黃素之同質異構物結晶篩選與核黃素螯合金屬有機網狀化合物，輔以濕式研磨法作為特定分子感測器之應用。

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蔡孟勳(Meng-hsun Tsai) 查詢紙本館藏

畢業系所

化學工程與材料工程學系

論文名稱

核黃素之同質異構物結晶篩選與核黃素螯合金屬有機網狀化合物，輔以濕式研磨法作為特定分子感測器之應用。
(Polymorphs Screening of Riboflavin and Riboflavin Chelated Luminescent Metal-Organic Framework: Identified by Liquid-Assisted Grinding for Specific Molecule Sensing via Chromaticity Coordinates)

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摘要(中)

化學感應器泛指具有高靈敏度、小體積，並對特定有機、無機或生化醫學物質具有相當高選擇性之偵測器。每一種化學感測器皆由化學感應材料辨識單元、訊號轉換單元所組成。由於化學感應材料必須盡可能對偵測分子具單一選擇性，且感應後所產生的訊號也必須要清晰及穩定的輸出。故化學感應器的化學感應材料之合成與設計，為化學研究上很有意義的挑戰。
核黃素因分子本身具有多牙基結構，可與許多金屬產生錯合物；此外核黃素也能透過氫鍵與水楊酸、3,5-二羥基苯甲酸、甲基胍胺、三聚氰胺等分子形成超分子水溶膠。故本論文嘗試利用具光激發光特性，且放光波長於可見光範圍的金屬有機網狀化合物作為感應訊號平台，將核黃素以錯合方式，接枝於金屬有機網狀化合物的結構上，藉以形成(有機金屬網狀結構)-(核黃素)的錯合晶體；並配合濕式研磨法，檢視作為感應分子的核黃素與可能之目標分析物，包括：水楊酸、3,5-二羥基苯甲酸、甲基胍胺、三聚氰胺等分子產生化學反應的難易度，以來預測形成(有機金屬網狀結構)-(感應分子) -(分析物)結合系統的可能性。而偵測到的光感應訊號將進一步轉譯於色度座標圖上，以獲得數值化的感測訊號結果。
此論文所提出的(有機金屬網狀結構)-(感應分子)-(分析物)感應系統是一個全新的概念，可破除金屬有機網狀結構作為感測器的孔洞限制，並增強與分析物的結合作用力；而濕式研磨法可以協助找出合適的感應分子，從而建立完整的感測系統。之後，也期望藉由這套方法找出更多可行性高的化學感測器系統。
除此之外，此論文也對核黃素的基本結晶特性進行探討，並蒐羅了歷年來所發表的專利文獻，從中發現核黃素存在六種同質異構物晶體，當中亦包含了三種水合物。為了統整所有資料，此論文也更進一步地建立所有核黃素同質異構物的相互關係圖、製造流程以及鑑定方法，期待此論文所提供的資訊能有效幫助日後對於核黃素的相關研究。

摘要(英)

Chemical sensor is generally defined as a detector with high sensitive, small size, and highly selective to special organic matter, inorganic substance, or biomedical substance. All the chemical sensors are composed by molecular recognition unit and signal transduction unit. Chemical sensing material must select the wanted analyte as specific as possible. Furthermore, the signal output that caused by binding with the analyte have to be distinguishable and stable. Therefore, the synthesis and design of the chemical sensing material are the significant challenges in chemical research.
Riboflavin has the polydentate ligand to form the complexes with different metals. Moreover, it also can form the supramolecule with salicylic acid, 3,5-dihydroxybenzoic acid, acetoguanamine, and melamine through the hydrogen bonding formation. Therefore, our research uses visible-light emitting metal-organic frameworks (MOFs) as a sensing platform, and riboflavin molecules are grafted on the framework structures by chelation to form the (MOFs)-(riboflavin) chelating crystals. Besides, liquid-assisted grinding can help to check the interactions between the sensing molecule (i.e. riboflavin) and target analytes (i.e. salicylic acid, 3,5-dihydroxybenzoic acid, acetoguanamine, and melamine), then, to predict the possibility of forming (MOFs)-(sensing molecule)-(analyte) binding system. Finally, the detecting light signal will further translate to the chromaticity coordinates to quantify the sensing results.
The (MOFs)-(sensing molecule)-(analyte) sensing system is a novel concept, it can overcome the limitation of size exclusion of MOFs sensors, and strengthen the binding interaction with analyte. On the other hand, the search for the candidate of sensing molecule can be easily and rapidly achieved by liquid-assisted grinding to develop a complete sensing system. Afterwards, we expect to construct more possible chemical sensing systems using this strategy.
Apart from this, this thesis also investigates the fundamental crystallized properties of riboflavin, and collects information about riboflavin from different patents. In these patents, we find that six polymorphs of riboflavin have already been published, including three types of hydrates. Furthermore, to summarize the significant data, the polymorph transformation diagram, manufacturing procedures, and characterized principles are provided as well. We hope these data we offer in this thesis will aid the related research about riboflavin in the future.

關鍵字(中)

★ 化學感測器
★ 金屬有機網狀化合物
★ 核黃素
★ 色度座標圖
★ 濕式研磨法

關鍵字(英)

★ Chromaticity coordinate
★ Liquid-assisted grinding
★ Chemical sensor
★ Riboflavin (vitamin B2)
★ Metal-organic framework (MOF)

論文目次

摘要 i
Abstract iv
Acknowledgement vi
Table of Contents vii
List of Figures xii
List of Tables xix
Chapter 1 Executive Summary 1
1.1 Chemical Sensor 1
1.2 Metal-Organic Frameworks Materials as Chemical Sensors 4
1.3 Brief Introduction of Riboflavin 7
1.4 Brief of Melamine and Sensing Techniques 9
1.5 Conceptual Framework 12
1.6 References 14
Chapter 2 Analytical Instruments 31
2.1 Introduction 31
2.2 Microscopic Method 35
2.2.1 Polarized Optical Microscopy (POM) 35
2.3 Crystallographic Analysis Method 38
2.3.1 Powder X-ray Diffractometry (PXRD) 38
2.4 Thermal Analysis Methods 41
2.4.1 Differential Scanning Calorimetry (DSC) 41
2.4.2 Thermal Gravimetric Analysis (TGA) 43
2.5 Spectroscopic Methods 45
2.5.1 Fourier Transform Infrared (FT-IR) Spectroscopy 45
2.5.2 Photoluminescence Spectroscopy (PL) 48
2.6 Conclusions 51
2.7 References 52
Chapter 3 Polymorph Screening, Property Characterization of Riboflavin and Synthesis of [AgL]n‧ nH2O 57
3.1 Riboflavin 57
3.1.1 Polymorphs 58
3.1.2 Riboflavin-Metal Chelates 58
3.1.3 Bicomponent Hydrogels of Riboflavin 60
3.2 Metal-Organic Frameworks 62
3.2.1 [AgL]n‧ nH2O 62
3.3 Materials 63
3.3.1 Chemicals 63
3.3.2 Solvents 63
3.4 Experimental Methods 64
3.4.1 Polymorphs Screening of Riboflavin 64
3.4.2 Hydrothermal Synthesis of AgL 65
3.5 Analytical Measurements 67
3.5.1 Optical Microscopy 67
3.5.2 Fourier Transform Infrared (FT-IR) Spectroscopy 67
3.5.3 Powder X-ray Diffractometry (PXRD) 67
3.5.4 Differential Scanning Calorimetry (DSC) 68
3.5.5 Thermal Gravimetric Analysis (TGA) 68
3.5.6 Photoluminescence Spectroscopy (PL) 69
3.6 Results and Discussion 70
3.6.1 Riboflavin 70
3.6.1.1 Polymorph Screening of Riboflavin 70
3.6.1.2 Characterization 71
3.6.1.3 Solubility 75
3.6.1.4 Photoluminescence 75
3.6.2 AgL 76
3.6.2.1 Characterization 76
3.6.2.2 Photoluminescence of AgL 79
3.7 Conclusions 81
3.8 References 82
Chapter 4 Riboflavin Chelated Luminescent Metal-Organic Framework: Identified by Liquid-Assisted Grinding for Specific Molecule Sensing via Chromaticity Coordinates 87
4.1 Introduction 87
4.2 Commission Internationale de l’Eclairage (CIE) 1931 Chromaticity Coordinates 91
4.3 Materials 94
4.3.1 Chemicals 94
4.3.2 Solvents 94
4.4 Experimental Methods 95
4.4.1 Liquid-Assisted Grinding 95
4.4.2 Synthesis of (AgL)-(Riboflavin) Chelation Crystals 95
4.4.3 Molecule Sensing by (AgL)-(Riboflavin) Chelation Crystals 96
4.5 Analytical Measurements 97
4.5.1 Optical Microscopy 97
4.5.2 Fourier Transform Infrared (FT-IR) Spectroscopy 97
4.5.3 Powder X-ray Diffractometry (PXRD) 97
4.5.4 Differential Scanning Calorimetry (DSC) 98
4.5.5 Thermal Gravimetric Analysis (TGA) 98
4.5.6 Photoluminescence Spectroscopy (PL) 98
4.6 Results and Discussion 99
4.6.1 Liquid-Assisted Grinding Method 99
4.6.2 Characterization of (AgL)-(Riboflavin) Chelation Crystals 105
4.6.3 Specific Molecules Sensing by (AgL)-(Riboflavin) Chelation Crystals 112
4.7 Conclusions 120
4.8 References 121
Chapter 5 Conclusions and Future Work 127
5.1 Polymorph Screening and Property Characterization of Riboflavin 127
5.2 Riboflavin Chelated Luminescent Metal-Organic Frameworks: Identified by Liquid-Assisted Grinding for Specific Molecule Sensing via Chromaticity Coordinates 127
5.3 Future Work 128
5.3.1 Developing Novel Sensing Systems 128
5.3.2 Fabricating (AgL) Thin Film 129
5.4 References 130

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指導教授

李度(Tu Lee)

審核日期

2012-7-11

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