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研究生： 愛爾華多
Atayde, Eduardo Jr. Clarito
論文名稱： 利用金屬有機框架觸媒之生物質轉化反應與其產物呋喃寡聚體應用於新型電致變色材料
MOF-Catalyzed Synthesis of Biomass-based Furan Oligomers and Their Application as New Electrochromic Materials
指導教授： 吳嘉文
Wu, Chia-Wen
倪其焜
Ni, Chi-Kung
口試委員: 何國川
Ho, Kuo-Chuan
陳林祈
Chen, Lin-Chi
康敦彥
Kang, Dun-Yen
葉禮賢
Yeh, Li-Hsien
學位類別： 博士
Doctor
系所名稱： 理學院 - 化學系
Department of Chemistry
論文出版年： 2024
畢業學年度： 112
語文別： 英文
論文頁數： 276
中文關鍵詞： 生物質 、呋喃寡聚物 、電致色變 、π-堆疊 、羥基烷基化-烷基化反應 、硫酸化MOF-808
外文關鍵詞： Biomass, Furan Oligomer, Electrochromism, π-Stacks, Hydroxyalkylation-Alkylation Reactions, Sulfated MOF-808
相關次數： 點閱：3  下載：0 
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    • 全球日益增加的能源需求促使研究人員制定了不同的策略，以利用可再生資源生成能源並減少能耗。根據此目標，本論文將介紹生物質材料轉化的方法，轉化出多種生物燃料前驅物的呋喃寡聚物，並將這些呋喃寡聚物應用於電致變色技術，這項技術相當適合應用於窗戶中達到改變透光性之目的，在永續建築中是相當重要的應用。
    本研究中呋喃寡聚物可以通過羥基烷基化/烷基化反應（HAA）的原位合成，且使用了首次介紹的酸性金屬有機框架材料之硫酸化MOF-808作為觸媒，以高產量和高選擇性生成多種呋喃寡聚物。結果顯示使用酸性MOF觸媒進行的HAA催化反應，可因為抑制2-甲基呋喃的自縮合反應，使主產物產率高達97%。該觸媒的高穩定性，使產率在重複性實驗中不會明顯的降低。除此之外硫酸化MOF-808還促使苯基電親試劑和呋喃衍生物的反應更容易進行，因此證明了硫酸化MOF-808的多功能性。
    針對呋喃寡聚物進一步研究了其電致變色性能，將tris(5-methylfuran-2-yl)methane（TriM）寡聚物引入原型電致變色器件後，藉由調控施加電壓，元件的顏色會隨著電位調控在透明的黃色與紅色之間進行可逆的變色。基於呋喃寡聚物的特性與表徵，電致變色元件在吸收波長為507 nm時具有1940 cm²/C的優異著色效率，並且具有相當優異的重複使用性，可持續1000次的切換循環。實驗和計算結果證實，寡聚物的著色是由於寡聚物陽離子自由基的可逆π-堆疊形成。本研究展現了優異的觸媒並有效地從生物質中轉化出寡聚物，並以此寡聚物取代其他有機電致變色材料，為開發新型有機電致變色打下良好的基礎。

    The world’s increasing energy demands has prompted researchers to formulate different strategies to generate energy from renewable sources and to also cut down energy usage. Aligned with these goals, this dissertation presents a means of generating different oligofuran-based biofuel precursors that can be obtained from biomass-based materials and introduces another application of these oligofurans in the field of electrochromism, which is fundamental in the development of smart windows for sustainable buildings.
    Furan oligomers may be synthesized using a one-pot approach by hydroxyalkylation/alkylation reaction (HAA). In this study, we introduce the first application of an acidic metal-organic framework, Sulfated MOF-808 in the catalysis of HAA reactions to produce a variety of furan oligomers with high yield and selectivity. Our results revealed that the use of the acidic MOF for our representative HAA reaction can generate a quantitative yield of 97%, while at the same time inhibiting the self-condensation of 2-methylfuran. It was also revealed that the catalyst is highly stable and can be reused many times without any significant degradation in its efficiency. The versatility of the catalyst towards the HAA process was also proven by its ability to facilitate the reaction involving benzene-based electrophiles and furan derivative.
    The generated furan oligomers were further investigated for their electrochromic properties. Upon incorporation of tris(5-methylfuran-2-yl)methane (TriM) oligomer into a prototype ECD, it was observed that it can undergo reversible transitions between a transmissive yellow state to red-colored state when subjected to different applied potentials. Additional characterizations have revealed that the furan-based ECD has a superior coloration efficiency of 1940 cm2/C at 507 nm and that it is stable enough to last 1000 switching cycles. It is also proposed that the coloration of the oligomer is due to the reversible π-stack formation of the oligomer radical cations as confirmed by both experimental and computational results. The ability to derive this oligomer from biomass and its simple synthesis process make it a formidable alternative to other existing organic electrochromic materials. In addition, this material may also serve as a base compound in the development of novel organic electrochromes.

    Chinese Abstract…………………………………………………………… ii English Abstract…………………………………………………………… iV Acknowledgement…………………………………………………………….. vi List of Publications……………………………………………………… viii List of Figures……………………………………………………………… xiii List of Schemes……………………………………………………………… xiii List of Tables……………………………………………………………… xiv Chapter 1. Introduction…………………………………………………… 1 1.1. General Aim and Specific Objectives of the Dissertation… 6 Chapter 2. Review of Related Literature 2.1. Lignocellulosic Biomass as a Source of Furan-based Compounds............................................... 8 2.2. Furan and its Oligomers…………………………………………… 10 2.3. Hydroxyalkylation-Alkylation (HAA) Reactions of Furan and its Derivatives……………………………………………………….….. 12 2.3.1. Heterogeneous Catalysts for HAA Reactions………………… 15 2.4. Metal-Organic Frameworks (MOFs)………………………………… 16 2.4.1. MOF-808 and Sulfated MOF-808……………………………. 17 2.4.2. Sulfated MOF-808 as Heterogeneous Catalyst for Different Organic Reactions……………………………………………..…………… 19 2.5. Electrochromism and Electronic Devices (ECDs)……………… 21 2.5.1. Typical Fabrication of ECDs and its Different Categories 22 2.5.2. Performance Indicators for Electrochromic Devices……… 23 2.5.3. Electrochromic (EC) Materials …...…………………………. 25 2.5.4. Organic Electrochromic Materials……………………………. 26 2.6. The Potential of Furan Oligomers as Electrochromic Materials 2.6.1. The Challenges of Using Furan for Electrochemical Applications……………………………………………………. 27 2.6.2. The Advantages and Electrochemical Applications of Conjugated Oligofurans……………………………………………………... 28 2.6.3 Furan as a Material for Electrochromic Devices….......… 29 Chapter 3. MOF-Catalyzed Hydroxyalkylation-Alkylation Reaction for the Controlled Synthesis of Furan Oligomers 3.1. Introduction…...…………………………………………………… 32 3.2. Experimental Section 3.2.1. Materials…..………………….……………………………….. 36 3.2.2. Synthesis of MOF-808………………………………………... 36 3.2.3. Synthesis of S. MOF-808……………………………………. 37 3.2.4. Analysis of the Acidity of the Catalysts……...………… 38 3.2.5. Typical Procedure for the Catalyzed Hydroxyalkylation/Alkylation Reaction………………………………… 38 3.2.6. Characterization and Instrumentation……………………….. 39 3.2.7. Analysis and Calculations…………………………………….. 40 3.3. Results and Discussion 3.3.1. Catalyst Characterization…………………………………….. 41 3.3.2. HAA Reaction and Catalyst Screening………………………. 44 3.3.3. Factors Affecting HAA Reactions……………………………. 52 3.3.4. Recyclability of S. MOF-808………………………………… 54 3.3.5. Derivatives of Trifuran Oligomers and Substituent Effect 56 3.3.6. HAA of Aldehyde-Containing Benzene Substrates…………... 60 3.4 Conclusions…………………………………………………………… 63 Chapter 4. Biomass-based Discrete Furan Oligomers as Materials for Electrochromic Devices 4.1 Introduction…………………………………………………………… 65 4.2. Experimental Section 4.2.1. General Synthesis of Oligofurans…………………………….. 67 4.2.2. Electrochemical Testing of the Synthesized Oligomers…… 68 4.2.3. Preparation of the NiHCF Counter Electrode………………… 68 4.2.4. Electrochromic Device Fabrication and Testing…………… 69 4.2.5. Computational methods……………………………………….. 70 4.3. Results and Discussion 4.3.1. Facile synthesis of furan oligomers………………………… 70 4.3.2. Electrochemical Characterization of the Trifuran Oligomers 71 4.3.3. Spectroelectrochemistry and Electrochromism of TriM…… 74 4.3.4. Cycling and long-term stability tests………………………… 78 4.3.5. Mechanistic Studies on the Electrochromism of TriM……… 81 4.3.6. Computational Studies………………………………………... 87 4.3.7. Other TriM-based Electrochromic Materials…………………. 89 4.4. Conclusions…………………………………………………………… 92 Chapter 5. Overall Conclusions and Future Perspective…………… 94 References…………………………………………………………………… 97 Appendix A…………………………………………………………………… 131 Appendix B…………………………………………………………………… 155 Appendix C…………………………………………………………………… 171 Appendix D…………………………………………………………………… 220

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