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http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/101040完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 姜昌明 | zh_TW |
| dc.contributor.advisor | Chang-Ming Jiang | en |
| dc.contributor.author | 陳奕文 | zh_TW |
| dc.contributor.author | Yi-Wen Chen | en |
| dc.date.accessioned | 2025-11-26T16:34:36Z | - |
| dc.date.available | 2025-11-27 | - |
| dc.date.copyright | 2025-11-26 | - |
| dc.date.issued | 2025 | - |
| dc.date.submitted | 2025-08-04 | - |
| dc.identifier.citation | (1) 鄺浚忠; 陳奕文; 馮竣麟; 張家維; 姜昌明. 光電催化應用於能源轉換與有機合成的簡介 化學 2024, 82, 263-285.
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Electrolyte effects on undoped and Mo-doped BiVO4 film for photoelectrochemical water splitting. J. Electroanal. Chem. 2019, 842, 41-49. (101) Li, Y.; Wei, Y.; Zhang, W. Oxidation behavior of N-hydroxyphthalimide (NHPI) and its electrocatalytic ability toward benzyl alcohol: Proton acceptor effect. J. Electroanal. Chem. 2020, 870, 114251. (102) Grunshaw, T.; Wood, S. H.; Sproules, S.; Parrott, A.; Nordon, A.; Shapland, P. D. P.; Wheelhouse, K. M. P.; Tomkinson, N. C. O. A Mechanistic Investigation of the N-Hydroxyphthalimide Catalyzed Benzylic Oxidation Mediated by Sodium Chlorite. J. Org. Chem. 2024, 89 (11), 7933-7945. (103) McGregor, J.-M.; Bender, J. T.; Petersen, A. S.; Cañada, L.; Rossmeisl, J.; Brennecke, J. F.; Resasco, J. Organic electrolyte cations promote non-aqueous CO2 reduction by mediating interfacial electric fields. Nat. Catal. 2025, 8 (1), 79-91. (104) Klahr, B.; Gimenez, S.; Fabregat-Santiago, F.; Bisquert, J.; Hamann, T. W. Electrochemical and photoelectrochemical investigation of water oxidation with hematite electrodes. Energy Environ. Sci. 2012, 5 (6), 7626. (105) Terry, B. D.; DiMeglio, J. L.; Cousineau, J. P.; Bartlett, B. M. Nitrate Radical Facilitates Indirect Benzyl Alcohol Oxidation on Bismuth(III) Vanadate Photoelectrodes. ChemElectroChem 2020, 7 (18), 3776-3782. (106) Klinova McMillan, N.; Lopez, D. A.; Leem, G.; Sherman, B. D. BiVO4 Photoanodes for TEMPO-Mediated Benzyl Alcohol Oxidation in Organic Media. Chempluschem 2022, 87 (10), e202200187. (107) Jouyban, A.; Soltanpour, S. Prediction of Dielectric Constants of Binary Solvents at Various Temperatures. J. Chem. Eng. Data 2010, 55, 2951–2963. (108) Tsukamoto, T.; Dong, G. Catalytic Dehydrogenative Cyclization of o-Teraryls under pH-Neutral and Oxidant-Free Conditions. Angew. Chem. Int. Ed. Engl. 2020, 59 (35), 15249-15253. | - |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/101040 | - |
| dc.description.abstract | 光電催化有機合成（photoelectrocatalytic organic synthesis, PECOS）因具備溫和的反應條件與獨特的產物選擇性，被認為是環保且具有潛力有機合成策略。然而，儘管具備這些優勢，對固液界面反應機制的理解仍然不足，限制了其更廣泛的應用。本研究中，我們以單斜白鎢礦型釩酸鉍（bismuth vanadate, BiVO4）作為光陽極，進行兩項光電催化反應。第一部分中，成功透過間接氧化機制將苯甲醇選擇性氧化為苯甲醛。研究結果顯示，反應效率受限於氧化還原介體－N-羥基琥珀醯亞胺（NHS）在電極表面的吸附，該吸附會形成有害的表面態，導致光生載子複合，並抑制NHS的完全再生。經鉬摻雜於BiVO4後，可有效降低表面態的生成，顯著提升催化效率。在最佳條件下，苯甲醛的生成速率達19.1 μmol cm-2 h-1，且選擇性與法拉第效率均接近100%。動力學分析亦顯示，鉬摻雜電極具有較長的吸附時間常數，佐證其產率提升之原因。
第二部分則以BiVO4光陽極直接氧化鄰-三聯苯（o-terphenyl），成功驅動分子內碳－碳鍵形成反應，合成三亞苯（triphenylene）。此為首次在光電化學條件下成功實現朔爾反應（Scholl reaction），為多環芳烴（polycyclic aromatic hydrocarbons）的綠色合成提供了新的途徑。這些研究結果不僅展現光電化學在有機合成中的應用潛力，也強調了對固液界面反應機制深入理解的重要性，為未來光電化學有機反應的設計提供了重要參考。 | zh_TW |
| dc.description.abstract | Photoelectrocatalytic organic synthesis (PECOS) has emerged as a promising approach for sustainable organic synthesis due to its mild reaction conditions and unique product selectivity. Despite these advantages, limited understanding of interfacial behavior and efficiency loss mechanisms remains a major challenge. In this study, monoclinic scheelite-type bismuth vanadate (BiVO4) photoanodes were applied to two light-driven reactions. First, benzyl alcohol was selectively oxidized to benzaldehyde through an indirect oxidation pathway. The reaction efficiency was found to be limited by the specific adsorption of the redox mediator N-hydroxysuccinimide (NHS) on the BiVO4 surface, which induced detrimental surface states, promoted charge recombination, and suppressed complete regeneration of NHS. Molybdenum doping effectively reduced surface state density and improved catalytic performance, achieving a benzaldehyde formation rate of 19.1 μmol cm-2 h-1 with nearly 100% selectivity and Faradaic efficiency. Kinetic analysis showed longer adsorption time constants for Mo-doped electrodes, corroborating the enhancement in reaction yield.
In the second part, BiVO4 was used to drive intramolecular C–C bond formation via direct oxidation of o-terphenyl, yielding triphenylene. This work represents the first successful demonstration of the Scholl reaction via PEC, offering a new sustainable route for synthesizing polycyclic aromatic hydrocarbons. Overall, this work highlights the potential of PEC in organic synthesis and underscores the importance of understanding interfacial mechanisms, providing valuable insights for the rational design of future PEC systems. | en |
| dc.description.provenance | Submitted by admin ntu (admin@lib.ntu.edu.tw) on 2025-11-26T16:34:36Z No. of bitstreams: 0 | en |
| dc.description.provenance | Made available in DSpace on 2025-11-26T16:34:36Z (GMT). No. of bitstreams: 0 | en |
| dc.description.tableofcontents | 口試委員會審定書 i
致謝 ii 中文摘要 iv Abstract v 目 次 vi 圖 次 ix 表 次 xv 縮寫對照表 xvi 第一章 緒論 1 1.1 研究背景 1 1.2 光電化學反應 2 1.2.1 光電化學反應的基本原理 2 1.2.2 光電極材料的選擇 3 1.2.3 光電化學技術之發展 4 1.3 光電化學在有機分子轉化的應用 6 1.3.1 氧化還原介體 7 1.3.2 醇類氧化反應 8 1.3.3 C－H鍵的官能基化反應 10 1.3.4 其他有機氧化反應 16 1.4 BiVO4光陽極 19 1.4.1 基本性質 19 1.4.2 晶體結構與電子結構 19 1.4.3 製備方法 21 1.4.4 本質限制 22 1.4.5 BiVO4的表面態 23 1.5 研究目的 26 1.5.1 理解固液界面行為－NHS介導的苯甲醇氧化反應 26 1.5.2 擴展PECOS的應用性－以光電化學形式驅動朔爾反應 26 第二章 實驗方法與原理 29 2.1 金屬－有機分解合成法 29 2.2 掃描式電子顯微鏡 31 2.3 X光繞射分析 32 2.4 拉曼光譜法 33 2.5 紫外－可見光光譜法 35 2.6 X光光電子能譜分析法 36 2.7 電感耦合電漿體質譜法 37 2.8 電化學分析方法 38 2.8.1 伏安法（Voltammetry） 38 2.8.2 計時電流法（Chronoamperometry, CA） 40 2.9 氣相層析法 41 2.10 化學試劑資訊 43 第三章 BiVO4薄膜的製備與鑑定 44 3.1 BiVO4薄膜之製備方法 44 3.1.1 FTO基材的前處理 44 3.1.2 BiVO4薄膜的製備 45 3.2 表面形貌分析（SEM） 46 3.3 結晶結構分析 48 3.3.1 BiVO4薄膜的XRD圖譜 48 3.3.2 BiVO4薄膜之Raman光譜 50 3.4 化學組成 52 3.4.1 BiVO4薄膜的X光光電子能譜 52 3.4.2 Mo:BiVO4薄膜的ICP-MS 56 3.5 光學性質（UV-Vis） 57 第四章 光電催化苯甲醇氧化反應 60 4.1 光電催化反應條件與產物定量方法 60 4.1.1 光電催化反應裝置架設 60 4.1.2 光電催化的標準反應條件與添加試劑設定 61 4.1.3 產物分析方式 62 4.1.4 產率、選擇性、生成速率與法拉第效率的計算方式 63 4.2 純BiVO4光陽極的光電催化表現 66 4.2.1 標準反應條件下的光電催化表現 66 4.2.2 各添加試劑在反應中的功能與角色分析 69 4.3 光電流衰減機制探討 72 4.3.1 光腐蝕機制之排除 72 4.3.2 擴散極限機制之排除 73 4.3.3 NHS再生能力的探討 74 4.3.4 氧化還原介體對NHS吸附的影響 75 4.3.5 輔助電解質對NHS吸附的影響 78 4.3.6 NHS－吸附與光電流衰減機制總結 82 4.4 吸附行為與異質表面態對催化性能的影響 83 4.4.1 NHS－的強化學吸附 83 4.4.2 異質表面態的形成 84 4.4.3 異質表面態對催化性能的影響 86 4.5 純BiVO4與Mo:BiVO4光電催化性能比較 88 4.5.1 Mo:BiVO4於標準反應條件下的光電催化表現 88 4.5.2 Mo摻雜對異質表面態濃度的影響 89 4.6 光電流衰減之動力學分析 92 4.6.1 雙指數衰減模型與時間常數比較 92 4.6.2 衰減時間常數的動力學探討 94 4.7 反應機制與應用展望 98 4.7.1 NHS介導的光電化學苯甲醇氧化反應機制 98 4.7.2 研究延伸與應用展望 99 第五章 光電化學方法的朔爾反應（Scholl Reaction） 100 5.1 反應條件與產物分析方法 100 5.1.1 光電催化反應裝置架設 100 5.1.2 產物分析方法 100 5.2 光電催化表現與反應條件優化 101 5.2.1 以DDQ作為氧化還原介體，間接氧化2-萘酚 101 5.2.2 光電化學直接氧化鄰-三聯苯 105 5.3 低產率原因之機制分析 110 5.3.1 添加試劑的光電性能分析 110 5.3.2 影響產率的因素與機制探討 111 5.4 未來展望與應用 115 第六章 結論 116 參考文獻 118 附錄 128 | - |
| dc.language.iso | zh_TW | - |
| dc.subject | 光電化學 | - |
| dc.subject | 光電化學有機合成 | - |
| dc.subject | 釩酸鉍 | - |
| dc.subject | 苯甲醇氧化反應 | - |
| dc.subject | 表面態 | - |
| dc.subject | 朔爾反應 | - |
| dc.subject | photoelectrochemistry | - |
| dc.subject | photoelectrocatalytic organic synthesis | - |
| dc.subject | bismuth vanadate | - |
| dc.subject | benzyl alcohol oxidation reaction | - |
| dc.subject | surface states | - |
| dc.subject | Scholl reaction | - |
| dc.title | 以釩酸鉍光陽極進行小分子的光電化學氧化反應 | zh_TW |
| dc.title | Photoelectrochemical Oxidation of Small Molecules using BiVO4 Photoanodes | en |
| dc.type | Thesis | - |
| dc.date.schoolyear | 114-1 | - |
| dc.description.degree | 碩士 | - |
| dc.contributor.oralexamcommittee | 楊吉水;吳恆良;鍾博文;王迪彥 | zh_TW |
| dc.contributor.oralexamcommittee | Jye-Shane Yang;Heng-Liang Wu;Po-Wen Chung;Di-Yan Wang | en |
| dc.subject.keyword | 光電化學,光電化學有機合成釩酸鉍苯甲醇氧化反應表面態朔爾反應 | zh_TW |
| dc.subject.keyword | photoelectrochemistry,photoelectrocatalytic organic synthesisbismuth vanadatebenzyl alcohol oxidation reactionsurface statesScholl reaction | en |
| dc.relation.page | 130 | - |
| dc.identifier.doi | 10.6342/NTU202502400 | - |
| dc.rights.note | 同意授權(限校園內公開) | - |
| dc.date.accepted | 2025-08-06 | - |
| dc.contributor.author-college | 理學院 | - |
| dc.contributor.author-dept | 化學系 | - |
| dc.date.embargo-lift | 2026-09-01 | - |
| 顯示於系所單位： | 化學系 | |
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